Tips for people dating widows and widowers

Sorry, this is not a steamy article that belongs on the topshelf of a grocery store magazine rack nor a racy novel by Anne Rice.


Instead, I hope to help anyone who has lost a spouse/partner and is trying to move forward with their lives and to experience love again.

In previous articles, I have explained my belief that love is an infinite resource and has the ability to multiply, again and again. For example, when a widow/widower is ready, they will expand their ability to love, and without guilt will be able to love two people at the same time. In case you’re wondering, I mean their late spouse and new partner.

The same also happens when a parent’s love doubles as their second child is born and triples as their third is born and so forth for each additional child.

Now that I have reasoned that I am able to begin dating again. Here are a few personal observations for anyone brave enough to date a widow/widower:

1) It’s not a competition.

Mary’s pictures are scattered throughout my house, her clothes and shoes fill the closets, and the kitchen is stacked with her favorite blue Churchill plates. It is safe to say, my entire house reflects Mary’s passion and style.

My home is an intimidating place for any woman I date. I’m sure my girlfriend asks herself, “how do I compete with Richard’s late wife?” “Is he ready to love me the way he loved his late wife?”

All good questions and here’s how I would respond to anyone dating a widow/widower.

Firstly, and most importantly, you’re not in a competition. It’s not you or their late spouse. Don’t try to downplay their late spouse’s importance in their life while finding ways to increase your own significance. That importance, and those memories, are ingrained in their life — forever!

Instead, find ways to honour their late spouse. Ask them about his late wife/husband. Find out about their passions, what they liked/disliked, their job, their parents and their family. Don’t be afraid to bring up their name during conversations.

Don’t ignore the existence of their late spouse. Find ways to merge their late wife/husband’s memory into the new relationship and focus on building new memories. Ask them if they would like to do activities that they did with their late spouse or would prefer to steer clear of things that might conjure up sad memories.

After two-years of soul-searching and contemplation, I found that I could love a new partner in the same way that I loved Mary, but only when I was ready. This included doing many things that I did with Mary, but also avoiding others!

If that makes you uncomfortable or you feel threatened, maybe dating a widow/widower isn’t for you.

2) Let them grieve special anniversaries.

I’m not sure if this will change, but for now, I take time off to honour and remember special anniversaries such as Mary’s birthday, our wedding anniversary and the date of her funeral. For me, these days will always be filled with a mixture of happiness, sadness, and grief.

I often spend these anniversaries with my children. My tip is to let them spend these days grieving. Don’t get upset if the anniversary doesn’t include you, or take their “mood” personally. These anniversary dates are about them and their late spouse. If you’re divorced, I’m sure there are dates that induce memories and feelings of sadness and grief.

Also accept that the anniversaries may cause rough patches in your relationship. Try asking the griever to discuss their pain but don’t pretend to be an expert or know how they feel. Or worse, demand they share their thoughts with you.

Sometimes space is the best measure to bring you closer together.

3) Children.

For me, my children are the most sensitive part of dating.

As many of you know, I have three children. When I shared my dating plan with my adult kids, their reactions were mixed. One fully supported the idea but the other two were upset and unwilling to continue the discussion. They admitted that dating was my decision, but they were not ready to accept another woman coming into our family home and acting like their mom (or my wife).

I assured the two protesters that no one would ever replace their mom, nor would I ever try to erase their mom’s memories.

As I began dating, I slowly began sharing my dating experiences with my children. I didn’t keep my dates a secret, but I wouldn’t provide details unless asked. Most importantly, I avoided bringing anyone home (while the kids were home).

I continued honouring all of Mary’s special anniversaries and I improved the lines of communication with each child. I also took a deeper interest in their lives and their issues. Basically, I worked on becoming a better father and when possible, I even tried to fill some of Mary’s roles (unfortunately, not very well).

Last Christmas, I noticed a shift, a softening of their views. All three kids, including the objectors, took an interest in my new relationship. I’m not exactly sure what caused the change, but I think they are beginning to feel that my new relationship doesn’t mean the end of my love for their mom nor forgetting her memories.

As parents, we are supremely protective of them. They will always be our main love. Whether you’re dating a widow/widower or a divorcee, my personal observation would be to treat their kids very carefully. Don’t try to become their new parent.

As adults, we should be able to connect with people (his or her children) on a friendly level without the need to adopt a “I’m older I know better” stance. Similarly, leave them to do the parenting, and if you don’t agree with their style, you should be able to discuss it openly and articulately enough to come to a fair resolution.

4) Mine, Yours, and Ours.

Mary and I worked very hard during our 33-year marriage, and we accumulated enough money in our estate for a comfortable retirement. Our business, our homes, our rental properties, assets, savings and investments are for my use, and when I die, will pass to my children. I’m quite clear that they’re not destined for anyone else.

Don’t get me wrong, I’m not paranoid that I will be swindled out of my assets by a scam or a fraud but I am concerned enough to have the “money” discussion with my new girlfriend and prepare a cohabitation agreement, if we ever decide to live together.

To minimize financial conflicts, I believe the “money” discussion should be had very early on in a new relationship, and I recommend the mine, yours, and ours strategy.

In short, my assets are mine and her assets are hers and if we buy anything together (like a house), it’s an “our” asset. On my death, my assets will be inherited by my children (same applies to her assets) and joint expenses will be shared equally, or as per a mutually agreed plan.

I would hope that anyone in their 50s/60s and dating again, would be financially independent and would not expect financial support from their new partner or his/her family. This goes both ways!

5) Take it slow.

Dating a widow/widower will test the patience of most people.

You’re dealing with their late spouse, their children, their family and their friends. You’re also dating their emotions (e.g., grief and guilt), so it’s normal for them to be a little testy at times, and it’s normal for you to occasionally be inpatient. As adults we’ve collected many life experiences and we should be able to use them to our advantage.

Take it slow. Don’t rush, don’t push, and don’t feel the need to be involved in every facet of their life. Let them set the pace.

Final thoughts

We all want love and to be loved. As a widower, I have been loved and continue to be loved by Mary, and I will continue to love her until my last breath. However, that doesn’t mean that I can’t or don’t want to be loved again, by another woman.

But widows/widowers do come with a little baggage. I’m not talking about a six-piece luggage set with matching carry-on bags. But I am talking about the memory of their late spouse.

One last note. Widowers have been through the ultimate relationship experience. One that no one ever wants to go through, not least in their 50s or 60s. But this experience does “maketh the man,” (and woman) so to speak. When you date a widower, you will be dating someone with many more experiences, a better grasp of their emotions, and someone (hopefully) that has fully stowed their baggage.

How can we help you through some of life’s most difficult transitions

We’re a small family at Dri Financial Group. We’ve been together for over 20-years. From years of experience, we’re able to provide the emotional support and financial expertise needed for every situation. If you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Interested in learning more? Here are a few resources for you:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.

source https://richarddri.ca/tips-for-people-dating-widows-and-widowers/

Financial advice for widows planning to remarry

There are many factors that can positively and negatively affect a relationship… excess baggage, shared interests, attraction and even cold feet.


But money and love are the real relationship killer. Later in life it can be tricky combining love, widowhood and wealth, but not impossible. Here is what I learned when I began dating again after the death of my spouse.

This is my story

I met my first love at the age of 18, we were both high school seniors. We dated in grade 13, became a couple in university and married at the young age of 24.

We didn’t have any financial assets, heck I’d never even heard of a financial plan. But we had good jobs and with some help from the banks of Mom and Dad, we bought a small condo in Etobicoke.

Back then, our financial life was very simple. We had one joint account where we deposited our salaries and paid bills. We worked, continued our studies, and enjoyed our weekends. Nothing could have been simpler.

As many readers know, Mary died in 2020 and I became a widower. I was left with a much different and complicated financial life. Mary and I had three wonderful children together, who have become the reason for my life — they are my definition of being rich!

Today, I own a business, a family home, rental properties, a vacation home, RRSPs, TFSAs and cash accounts. I’m a member of a corporate pension plan and I’m eligible for government benefits, including our federal pension and CPP survivor’s pension. It’s so complicated that I hire a bookkeeper, an accountant and a property manager to help with all the paperwork and day-to-day stuff. I’m not complaining but it is complicated to stay on top of all my financial stuff.

Mary and I worked very hard for our money, and I want our assets to be eventually inherited by our children (but only after I have used whatever I need).

But wait, how would my plan work if I decided to remarry or cohabitate with another woman? Are there some sensitive topics involving money that should be discussed before remarrying or living together?

Scroll down before swiping right

Are you ready to date again? Before setting up your profile on one or more online dating apps, ask yourself if you’re ready to date again. Trust me when I say, “this is not an easy question to answer,” and a question that I spent two years trying to answer.

I felt confident to date when I was able to reconcile the possibility of loving two women at the same time. After much contemplation, I realized that I could continue to love my deceased wife while at the same time, let myself fall in love with another woman.

At first, the thought of loving another woman felt like cheating on my wife but eventually a different perspective emerged, the idea of infinite love.

To explain the concept, I often use the example of having kids. When child #1 is born, they receive all of mom and dad’s love, yet when child #2 is born, mom and dad’s love somehow multiplies and now each child is loved equally. Notice, Love didn’t get subtracted from one and added to the other, instead, love miraculously doubled.

I believe when you have accepted the idea of infinite love, you’re ready to date again and to give your new partner the same love, devotion and commitment you gave your late spouse, without the feeling of guilty.

My secret to Money Harmony: mine, yours and ours

When you can honestly say that you’re ready to love again, start the dating process without any guilt. I’m not a dating coach so, I’ll skip the dating advice, but I will provide financial tips to consider when planning to cohabitate and possibly remarry.

Some of the happiest remarried couples have shared their belief that “money issues” often lead to relationship issues and it’s best to be transparent with money before getting too serious. Yes, I know it’s common sense to discuss money before getting too serious, but the topic is far from romantic and many couples just ignore the topic and hope it doesn’t cause too many problems down the road.

I believe many money issues may be resolved by applying the strategy of “mine, yours and ours.”

If we look at a scenario, how would a remarried couple handle different amounts of assets brought into the marriage. Example: Partner A’s net worth is $1,000,000 while Partner B’s net worth is $5,000,000.

If your goal is to pass your personal assets on to your kids when you die, then it’s important to hold your assets individually and let your partner understand that all of your remaining assets (if any) on death will pass to your kids, not him or her. This understanding must be legalized with a prenuptial or cohabitation agreement.

Thus, each partner would maintain separate banks and investment accounts and would select their individual children as beneficiaries of their assets. The partners would also choose third-party executors (family or a trust company) to help settle their respective Wills and estates. At the same time, the partners would appoint Powers of Attorney for property and personal care who will act in their best interest and are free of conflicts of interest.

Perhaps a joint chequing account may be opened and used to pay common expenses. It’s best to predetermine if common expenses are paid equally or based on some other allocation like the ability to pay or usage.

Other thorny issues

Sometimes, money issues may be very complicated, you can stick to the mine, yours and our strategy or you might need to be a bit more creative. Other things spring to mind when you have that “money” conversation:

a) Houses

If both partners own a house, which house do you live in, who owns it? How’s it paid for? Would the second home be maintained or sold? Or would both homes be sold to purchase a new home together?

How are household expenses allocated? Is 50-50 reasonable or should expenses be paid based on ability to pay or usage?

b) Retirement plans

Should both partners retire at the same time? Do both partners have enough money to maintain their lifestyle in retirement, if not, is the affluent partner prepared to support the other?

If both partners don’t retire at the same time, how are vacations organized and who pays?

c) Investment strategies

Do the partners follow similar investment strategies? If not, what happens when one portfolio outperforms the other, or even declines? Is the gain and loss shared or is it taken individually?

Do partners use the same professional advisors?

d) Health consideration

If one partner is sick, is the other partner prepared to help with time and or money? If not, who will provide the necessary assistance? How would care differ if one partner had appointed a Power of Attorney for Personal Care?

e) Kids and aging parents

If aging parents are still alive and become financially dependent, does one or both partners provide financial support? What about financial assistance for children, do both partners help out equally or at all?

Final thoughts

Getting remarried later in life can be very messy. Putting personal factors aside, partners may have vastly different assets and liabilities, partners may disagree on retirement goals or have dramatically different retirement lifestyle expectations. The challenges continue if a partner may be ladened with financially dependent children and/or parents. Like I said, messy!

But this financial messiness shouldn’t stop you from falling in love again and possibly remarrying.

From my personal and professional experience, it is critical to protect yourself and your family. This isn’t pillow talk so put some time aside to discuss money with your partner and use the “mine, yours, and ours” strategy to arrive at consensus then formalize your joint understanding with a legal document.

If your partner is unwilling to discuss money or is more willing to apply the strategy of: What’s Mine Is Mine, And What’s Yours Is Ours, maybe a little internal soul searching is needed before you ask the question again.

Have you started dating again? Do you think having the “money talk” early makes sense or do you feel it will jeopardize the budding relationship?

How can we help you through some of life’s most difficult transitions

We’re a small family at Dri Financial Group. We’ve been together for over 20-years. From years of experience, we’re able to provide the emotional support and financial expertise needed for every situation. If you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Interested in learning more? Here are a few resources for you:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.

source https://richarddri.ca/financial-advice-for-widows-planning-to-remarry/

I lost my spouse and now I’m dating — why do I feel guilty?

Roses are red, violets are blue


As we move into February, my thoughts turn to red roses, heart-shaped chocolates and Valentine’s Day. But wait a minute, I’m a widower, can I date? Is that even allowed?

What will my family and friends think if I’m seen holding the hand of another woman? As I begin to date again, as a widower (and I’m sure widows feel the same) guilt and worry continue to swirl around my head.

Discover how I combined my endless love for my late wife and developed a new loving relationship with another woman. Everyone deserves to be happy. It is possible to share your life with someone else and to move forward without feeling guilty.

This is my story.

I lost my spouse and now I’m dating — why do I feel so guilty?

For most folks, February is known for snow, the super bowl, a bit more snow, and hopefully (if money and restrictions allow) a spring-break respite from, yeppers, the snow!

But for me, February is the month of love. I would spend hours planning a special Valentine’s Day (and evening) for my wife, including gifts, flowers and a romantic dinner or a play. But that all ended in January, 2020 when Mary passed away of ovarian cancer.

During my first Valentine’s Day as a widower, I had no interest in dating or even speaking to someone new. Mary had been dead for less than a month and I was in the grips of bitter grief. Everything hurt!

My second Valentine’s Day was in 2021, and I’m not going to lie, I believed that I had a better handle over grief. But in hindsight, time had allowed the “brain fog” to clear and with a clearer mind I was able to grasp and feel the full magnitude of what had happened. For me, the second year after Mary’s death was actually more difficult than the first.

I’m not sure how I managed but I forced myself to ask someone to dinner for Valentine’s Day, 2021. The date went well, and I enjoyed her company and conversation, but I couldn’t shake my guilt.

The many faces of guilt

Mary and I never discussed seeing another woman after her death, and for the longest time, I felt that she hadn’t given me permission to date. This lack of permission added a new guilt to my list of guilts, (including survival guilt), and every time I looked at a woman, it felt like I was cheating on Mary.

My first date after Mary, was at an outside patio in Yorkville and instead of getting to know my date, I was constantly checking if friends or family were around to see me with another woman. I left feeling guilty for having had fun and spending time with a woman who wasn’t my wife.

I felt conflicted, on one hand I was having fun meeting new people,

I felt conflicted, I was having fun with new people, but I couldn’t help thinking that my happiness was paid for by Mary’s death.

The guilt that had me checking over my shoulder

I’m a relatively confident man. I’ve never been too worried about what people think of me because I’ve never been in a situation to warrant concern.

But here I was, worrying what people would think as I walked out with another woman.

As a father, my main concern was (and always will be) my three children: Victor, Gordon and Christine. For over a year, I could hear their voices in my head, “Is dad replacing mom?” “Does dad want us to forget mom?” With the ever-present echo of my friends, “It’s too soon to date?”

I began dating about one year after Mary’s death. I can’t give anyone advice about the appropriate time to begin dating; it’s personal and it can be 2 months, five years or whenever. It’s a personal decision and should be left the griever.

Please don’t judge a griever until you have “walked a mile in their shoes.” The stages of grief vary from person to person and the time spent in each stage may be long or short. There are no set rules for how long grieving should take nor does a bell ring to signal that it’s appropriate to start dating again.

Not moving on, just moving forward

Kathleen Rehl’s book entitled “Moving forward on your own” helped me reconcile many of the guilts connected to dating after Mary’s death.

Kathleen explained how I could date and find happiness in my new life while still respecting my past life with Mary. After hours of mulling over these words, I now understand that it’s possible to begin a new relationship while always loving my deceased wife.

To my children, I say “the love that I have for your mother is endless, just like the love I have for you!”

I want them to know that when Victor was born, mom and I loved our little boy with all our heart and wondered if we had room to love another child. When Gordon was born, we didn’t subtract love from Victor to give to Gordon, instead our love doubled. And when Christine was born, our love tripled.

Love is not finite, instead it’s an endless resource.

Valentine’s 2022 (the third after Mary’s death)

Today, I feel healthier that I have reconciled many of the guilts connected to Mary’s death. This year, I will spend Valentine’s Day with a woman I have recently met, and I will be enjoying her company without worrying about who will see us.

Although Mary never gave me permission to date after her death, I now believe that she didn’t withhold her permission out of spite or malice but because of her own issues dealing with her death.

Much is written about death having five stages, if this is true, Mary had difficulty getting past the denial stage and moving to acceptance. Please believe me, I’m not being critical, I have absolutely no idea how I will handle my own death when the day comes. Hopefully I will be able to learn from Mary’s experience.

Next week I’ll look at some of the financial considerations when a widow or widower finds a new love of their life, stay tuned (sorry folks, I just couldn’t help myself, the financial considerations are so important).

A Valentine’s tip for widows and widowers

Loving another woman/man is not a betrayal of your late wife/husband nor should you care about what others think. Begin dating when you have found a way to move forward without forgetting your late spouse.

How did you manage the emotional issues connected to dating after the loss of your partner? Did you feel guilty? How did you overcome your guilt?

How can we help you through some of life’s most difficult transitions

We’re a small family at Dri Financial Group. We’ve been together for over 20-years. From years of experience, we’re able to provide the emotional support and financial expertise needed for every situation. If you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Interested in learning more? Here are a few resources for you:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.

source https://richarddri.ca/i-lost-my-spouse-and-now-im-dating-why-do-i-feel-guilty/

Who’ll take care of me if I have an accident

A Power of Attorney for Personal Care is a critical part of your estate planning.


It allows a trusted person to make decisions on your behalf when you do not have the capacity to do so.

I realize that “personal-care decisions” sounds more like hair and nails, and all that! And there is certainly an element of caring for the personal aspects of someone’s life, but it is much more than that!

Nuffin’s gonna ‘arm us.

I’m as bad as anyone. We feel invincible and nothing serious will ever happen to us, but…. occasionally an accident or a serious illness occurs, and it could leave us incapable of making personal-care decisions.

From my experience, most clients consider a Power of Attorney for Personal care to be used when/if a life-or-death decision needs to be made, such as to refuse or accept life support. However, it is also used for many other important decisions based on our wellbeing, such as housing and personal care.

An attorney decides where you will live, what you will eat and if you need caregivers. They will also understand your medicines and treatments. Based on your original requirements, they will decide how you dress, how often you see your friends, how often you exercise, and yes, how often you get a haircut. You can even tell them that you want your parting on the left, not the right!

That’s why it is an important position and why you must choose your attorney carefully. They must be:

  1. Someone you trust and who will act with your best interests in mind,
  2. free of conflicts of interests which may prevent them from acting according to your wishes, and
  3. must be familiar with your wishes and have the strength to be your steward (when you cannot).

As real as it gets!

Early in 2020, I received a frantic call from Anne (not her real name) explaining that her best friend Jane (also not her real name) had suffered a brain aneurysm and was now in a coma. Anne was extremely concerned about Jane’s health and was horrified to learn that she was chosen to be Anne’s Power of Attorney for Personal Care.

Anne said, “but we never talked about this issue and I have no idea what Jane wanted me to do, I guess Jane thought it would never happen to her. Now what?”

This article provides a general overview of the responsibilities under the Power of an Attorney for Personal Care and why we must select wisely. Please recognize that I’m not providing legal advice, nor am I covering Power of Attorney for Property.

What is a Power of Attorney for Personal Care in Ontario?

In non-legal terms, a Power of Attorney for Personal Care gives Anne the authority to make personal-care decisions in the event Jane becomes incapable. As she did after her brain aneurysm.

Based on this scenario in Ontario, Anne is now called the “attorney” and is responsible for making decisions on behalf of Jane, for the following1:

  1. Healthcare,
  2. housing, and
  3. other aspects of Jane’s personal life, such as meals and clothing.

From my experience, clients see attorneys as these high-powered individuals striding around a courtroom, akin to Al Pacino as he shouts “this whole courtroom is out of order” in his 1979 movie, …And justice for all. But the reality is very different.

For one, in this situation, an attorney isn’t necessarily a trained lawyer. It can be a family member or even a trusted friend, or friends.

In fact, many people understand that the role of “attorney” is just to make life or death decisions (i.e. accepting or refusing medical treatments). But the truth is, it is a great responsibility for an individual with many finer nuances. For example:

  • The attorney must decide where Jane lives: at home or in an institution.
  • What Jane eats (consideration must be given to special diets).
  • If Jane should receive caregivers (if at home): how many, how often and their responsibilities.
  • Jane’s clothing, personal hygiene, haircuts, outings etc.
  • An understanding of Jane’s drugs, treatments, and procedures.
  • A list of Jane’s personal and professional contacts, including doctors and medical professionals.

Do I need a Power of Attorney for Personal Care?

I can only speak for myself, but I strongly believe that selecting a Power of Attorney for Personal Care is an essential part of your estate planning. Here’s what I would discuss with my attorney:

Housing

For me, I’d like to stay in my home for as long as possible and hire caregivers to provide the necessary care, until a point where my health is suffering or it is dangerous for my health to be left alone.

Food

Since I don’t have religious considerations, my diet can be prepared according to the Canadian Food guide’s recommendations. With my daily Double Double of course.

Life support

I refuse artificial life support if I’m terminally ill or mentally incapable of returning to a normal life.

Personal hygiene

Ideally, I’d expect appropriate care for hair (every three weeks), clothing (business casual wear), outings (daily walks if possible), seeing friends (weekly, if possible) etc.

Wherever possible, it’s important to select an attorney without conflicts of interest. For example, if your beneficiary is selected as your attorney, they may be incentivised to minimize the cost of your care to maximize the value of your estate, which isn’t good for you. At the end of the day, you’ve earned your daily Double Double, but a beneficiary may not see it that way.

In fact, it is important to keep beneficiaries separate from attorneys and executors.

Also, it’s best to appoint someone who lives in Canada and ideally in Ontario. The attorney must respond quickly, monitor how you’re doing and make sure your needs are met, which could be difficult if they’re abroad or in Vancouver, for example.

— — Your attorney must be someone you can trust and someone who will act in your best interest at the appropriate time — —

What if I don’t have one of these contracts?

If you become incapable of making health decisions and don’t have a Power Of Attorney for Personal Care, the Health Care Consent Act determines who can make decisions, in this order2:

  • Your spouse or partner.
  • Your parent, or your child if they are at least 16 years of age.
  • Your brother or sister.
  • Any other relative.
  • The Office of the Public Guardian and Trustee.

If you’re estranged from your spouse or family, it could become a difficult situation. More specifically, it could become a difficult situation that you have absolutely no effect upon! This is exactly why you need a Power of Attorney for Personal Care.

Who can be an Attorney for Personal Care?

It’s a very flexible contract. You can appoint one attorney or a group of attorneys to manage your personal care, but you must decide if they are to act jointly and agree on every decision, or if they may act jointly and separately.

You can also appoint substitute attorneys in case one can’t act as your attorney at the time, or doesn’t want to act when they need to.

The person or persons must be mentally capable and be at least 16 years old to be made a Power of Attorney for Personal Care.

So, is this just a form from the Post Office?

You can complete a power of attorney document yourself for free or have a lawyer do it. To create the document yourself, you can either3:

The decision to use a lawyer or not comes down to personal choice and how comfortable you are with these documents. Obviously, there is a fee if you ask a lawyer to draft the document. Also, if you appoint your lawyer as your Power of Attorney for Personal Care, there will be a fee drawn from the estate for his/her services.

Care doesn’t come for free

I love and care for many people, and I’d do anything for them, but many aspects of the role of Power of Attorney for Personal Care, must be covered financially by the estate of said person. As the attorney, it is critical that you know that any care needs can be covered by the estate. You don’t need to know how much they have in the bank or whether they have a villa in Jamaica, but you do need to know that costs can be covered.

Likewise, it’s important to ensure that your wellbeing can be covered. This might be via your employers insurance (or previous employer if you’re permanently incapacitated). Or your own individual health, life, disability or long-term care insurance policy. Make sure to have these documents kept in a safe place for your attorneys.

It is likely that a separate Power of Attorney has been appointed to look after the financial needs of the individual. So it’s important that you know this person and periodically liaise with them to ensure that you can continue your role in a manner befitting the individual.

Final thoughts

Selecting a trusted attorney is often the last topic most people discuss, obviously it’s not a happy or uplifting topic, but accidents can happen, and some accidents (or illnesses) are so serious that they leave us incapable of making personal-care decisions (temporarily or permanently).

For me, I have already selected someone as my attorney. I feel comfortable knowing that I have selected a person I trust, who will act in my best interest, and we have discussed my wishes. It’s one less thing to worry about as I enter a new chapter of my life.

Have you selected your Power of Attorney for Personal Care yet? The team at Dri Financial Group are always available to discuss all aspects of estate planning, including insurance policies. If you’re unsure about this contract or simply what to catch up on your planning, feel free to reach out to our team at any time.

In fact, if you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Learn more:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.


1 https://www.ontario.ca/page/make-power-attorney
2 https://www.cleo.on.ca/en/publications/power/what-if-i-do-not-have-power-attorney-personal-care
3 https://www.ontario.ca/page/make-power-attorney

source https://richarddri.ca/wholl-take-care-of-me-if-i-have-an-accident/

Checklist: What to do after losing a loved one

Dealing with this loss can be an immensely emotional and overwhelming process.


During this difficult time, it is common to be confused or uncertain about your next steps personally, legally, and financially.

To help you get through this process, we’ve created a checklist of what you need to do when you lose a loved one. The steps below outline the main areas to cover, from the day your loved one passes away to when the estate administration is completed.

Continue reading “Checklist: What to do after losing a loved one”

Richard Dri Canadian dividend growth model

Executive summary

The Richard Dri Canadian Dividend growth model – 20-years on. Learn the story behind the dividend growth model that’s consistency delivered attractive risk adjusted returns  for 20-years

So much happened during the last twenty years: the aftermath of 9/11, the financial crisis of 2008, historically low interest rates, quantitative easing by the central banks and more recently, the economic repercussions of the pandemic.

So, I thought it would be a great time to evaluate how my flagship model performed during such extreme conditions.

Given that most of my clients were/are retired or pre-retired and require cash flow to fund retirement lifestyle expenses, it was important for the model to concentrate on the following objectives:

  1. Stocks that paid increasing dividends,
  2. stocks that were less volatile against the S&P/TSX, and
  3. stocks that performed well against the S&P/TSX.

Read this article for my analysis but here’s a hint: during 2021, the model’s stock prices and dividends were both up… significantly.

The year is 2022!

This year marks the 20th anniversary of my flagship model that I shamelessly called the “Richard Dri Canadian Dividend growth ” model.

Today’s article looks back at why I created the model, and possibly more importantly, whether the model has achieved the objectives established back in 2002.

Some history

After completing a four-year stint as a public accountant with a major Canadian accounting firm, I decided that I was ready to expand my wings and start an investment firm. The year was 1992 and the Canadian economy was struggling through a deep recession. Few people were interested in RRSPs, stocks or mutual funds, so the timing couldn’t have been worse. Nevertheless.

As I have written in past articles, the early 1990s were financially difficult for me and my family and I was close to financial bankruptcy.

I should mention that we had two bright spots, the birth of our first son in 1991, followed by the birth of our second son in 1994. Personally, it was a magical time for me, I loved playing and laughing with my young kids and spending time with Mary, as a family of four.

Professionally, I persisted and by the late 1990s, the Canadian economy began to recover, and my little investment firm began to grow and flourish.

We provided mutual funds, insurance and after qualifying as a Certified Financial Planner, we offered personalized financial planning services to Canadian pre-retirees.

Looking back, it was an exciting time to be in business, however, I had a nagging question that kept popping up and I couldn’t find the right answer. I kept asking myself, “how do I consistently find tomorrow’s top-performing stocks?” I didn’t have the answer, but I had a hunch that the study of history held the answer to my question.

A chance encounter with a professional investor

I’m sure you heard the following saying, “when the student is ready, the teacher appears.” My teacher was an experienced and successful long-term investor (not a speculator). Through a review of historical data, he proved that the best-performing stocks share many common characteristics.

At first, I had trouble understanding the lesson, then I remembered my aunt, who’s a teacher. She claimed she could identify the best-performing students on the first day of school. Over her many years of teaching, she learned that the best-performing students shared certain “success characteristics” which increased their odds of becoming top students.

Once she determined which students had some or all of these “success characteristics,” she believed she could guess the honour roll students before any tests or exams were written.

After many hours of study with my investment guru, a two-step investment process was developed:

  1. Study the best performing stocks of the last 30-years and identify the common characteristics they shared,
  2. find today’s stocks displaying these characteristics, and
  3. reapply the filter each quarter and replace stocks that are no longer sharing the characteristics with stocks that do.

The birth of the Richard Dri Canadian Dividend Model

With the assistance of a research company called Computerized Portfolio Management Services (today part of Morningstar research), we identified 10 common characteristics found in the best performing dividend stocks of the last 30-years and with this information we built the computer model needed to screen and rank today’s stocks displaying these characteristics.

I should add a note here that we only studied dividend paying companies because our clients were either retired or pre-retirees and needed cash flow to fund their retirement lifestyle.

By screening stocks against the 10 filters identified from the study, a list was generated ranking stocks based on how well they matched the filters. The model then selected the top 20 stocks and held each stock until the stock’s ranking fell below the 33 percentile, if/when this occurred, the stock was replaced with the next highest ranking stock.

The study also noticed that dividend increases often led to stock price increases, hence we tweaked the model to give additional importance to stocks displaying consistent dividend increases.

As of December 31st, 2021, how has the model performed?

The compounded investment returns are as follows

1 year 17.8%

3 years 13.3%

5 years 8.2%

10 years 12.7%

From inception (December 31st, 1990) 13.8%

(Before fees and reinvesting all dividends)

Richard Dri Models

How about dividend increases?

What a year for dividend increases… As of December 31st, 2021, 19 of the 20 companies in our dividend model increased their dividends in 2021. The dividend increases were as high as 38% for Newmont Corp and Quebecor, and the average increase for the 20 stocks within the portfolio was 13.75%.

I couldn’t be happier with the dividend increases, many of our clients are retirees and the bulk of their retirement income comes from dividends so, when the model’s dividend increases by almost 14%, retirement cash flow also increases.

Richard Dri Models

In addition, if our research is correct and stock prices follow dividend increases, then the future looks promising for our dividend growth stocks.

Final thoughts

From the model’s inception on December 31, 1990, it has consistently outperformed the S&P/TSX index (13.8% vs 8.9%), and demonstrated lower risk and volatility than the index (0.6 beta vs 1 beta for the index).

As the creator of this model, I have seen it grow, evolve and consistently meet its objectives. Akin to a father to his child, I’m proud of what you’ve achieved. As a portfolio manager, I’m very happy with the investment model’s long-term investment performance and I look forward to better or similar returns over the next 20-years.

However, I caution investors (especially newer investors), stock prices move in two directions: upward and downward. Investors must be prepared and expect months or even years when the market direction is downward.

Yet, despite negative returns, the model’s long-term performance has historically rewarded investors with investment returns greater than those offered by guaranteed investments, such as government bonds.

I hope that I’ve inspired you to relook at your financial planning. If you need help, call my office and book an appointment. We will help you start 2022 in a positive and profitable way. In fact, if you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Learn more:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.

source https://richarddri.ca/richard-dri-canadian-dividend-growth-model/

Dri Financial Group’s top five podcasts

Following my top five articles of 2021, it would be remiss of me if I didn’t include my top five podcasts as well.


For me, my podcasts are more than just words. They’re an opportunity to meet new people, to reconnect with old friends, and to continue learning about this wonderful industry that I’ve called home for over 25-years.

The feedback that I get tells me that you enjoy our podcasts too. Maybe you listen to them over your morning coffee or maybe you read the transcript on your way to work. Either way, you find them interesting and informative, and that’s exactly what we hoped when we created them. Look out for exciting new interviews, content and more…

During the year, we’ve released or rerun a podcast every week, on topics ranging from real estate to retirement planning and everything in between. In 2022, I plan to concentrate on the issues affecting people in the midst of a major life transition, such as:

  1. Planning for retirement,
  2. Going through a divorce, or
  3. Becoming a widow or widower.

Thank you for listening to my podcasts. AND NOW, the top 5 podcasts, in descending order:

#5 Building a breakfast business with Tony Cappellano

In this episode, I had the pleasure of chatting with the late Tony Cappellano, who passed away recently. Tony was a Toronto-based entrepreneur and restaurant owner who founded the Boom breakfast chain with locations throughout the Greater Toronto Area. Tony was a veteran of the food industry, invested in real estate, and could speak firsthand as to what it takes to be a successful entrepreneur. He believed that the more money and effort you put into training employees, the better they will be at winning over customers and making them feel at home. Learn more about what motivated him to start his own businesses.

#4 Disrupting the Real Estate Industry with Robert Price

Robert Price, Founder and CEO of Bode Canada, joined me for this podcast. Bode Canada, an online real estate brokerage is really disrupting the industry as it makes selling real estate simple, transparent and more economical. In our conversation, Robert shared a great deal of information about Bode, including its current status and finances, plans for expansion, biggest challenges as a start up, and its original and potential future funding. Finally, he explained how he describes Bode to real estate agents and brokers. Our interview drew to a close with Robert sharing the ways in which he invests and protects his money, and his definition of financial independence. Click here​ to listen to his words of wisdom.

#3 Making the Legal Profession Faster, Better, and Cheaper with Aaron Baer

On this episode I was joined by Aaron Baer, partner of the law firm of Aird and Berlis LLL, for a conversation about ways to make the legal profession faster, better, and cheaper. Aaron practices corporate and commercial, but the focus of our interview was his keen interest in legal technology, which has played a leading role in his firm’s adoption of artificial intelligence, legal project management and data analytics. So, in our call, Aaron discussed the ways in which technology can help lawyers and their clients. Aaron was filled with valuable information and ideas, and he shared so many of them during our podcast. Listen again to my informative podcast with Aaron Baer.

#2 Disrupting the Financial Sector with Jeff Adamson

Jeff Adamson, Co-Founder of NEO Financial, was my very special guest on this podcast. As the Co-Founder of SkipTheDishes, Jeff disrupted the food delivery business by identifying a consumer expectation gap and designing a more efficient and mutually rewarding system. He and his team at NEO continue to push traditional boundaries, and at the time of our podcast interview, they were hard at work trying to do something similar with the financial sector. Jeff’s passion for change is infectious. Click here​ to listen to the full podcast and his vision for the future of NEO.

#1 Finding Success Through Building a Collective Legacy with Mohamad Fakih

In the #1 spot is my thoroughly fascinating podcast interview with Mohamad Fakih, CEO of Paramount Fine Foods. Originally from Lebanon, Mohamad eventually made his way to Canada with very little money, and has gone on to create a highly successful empire and legacy through his commitment to putting people first. In addition to his current CEO role, he is the Chairman of Fakih Foundation, the Voice of UNHCR Canada, an award winning entrepreneur, and above all, a passionate and well respected philanthropist and activist. In fact, Mohamad was inducted to the Order of Canada (CM) in the 2021 Christmas honours list. I might be biased but it really was a good interview. Listen again to my conversation with Mohamad Fakih (CM).

Final thoughts

I believe that part of the success associated with our podcasts is due to the preparation that we do beforehand. Our due diligence towards our guests, the writing and rewriting of the questions, and the research that we conduct ensures that answers are meaningful and logical. The night before, I’m always up late, honing the prep work ready for the next day’s interview.

Together with the interview itself, there’s a lot to do, and I’ll be honest with everyone; I wouldn’t change a single thing. I thoroughly enjoy listening and learning from all of our guests. I hope you feel the same, and if they inspire you to relook at your financial planning, call my office and book an appointment. We will help you start 2022 in a positive and profitable way.

In fact, if you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Learn more:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.

source https://richarddri.ca/dri-financial-groups-top-five-podcasts/

Dri Financial Group’s top five articles of 2021

As I write this article on the last day of 2021, I can’t help but reminisce about the themes that we’ve covered during the year.


Some articles were interesting to research, some discussed difficult life situations and others covered technical issues about tax or retirement planning. I enjoyed writing each article and I especially loved reading and responding to the feedback from the readers.

During the year, we wrote 46 articles (one was written by Lora Shapiro) and the articles covered a variety of financial planning issues. I can summarize the themes into five general categories:

  1. The Financial challenges of losing a spouse,
  2. How to create retirement income for life,
  3. Helpful tips to defer tax (i.e., RRSPs, TFSA, RESPs, RDSP, life insurance),
  4. What to do with the family cottage after first death, and
  5. Living off a dividend income.

In 2022, I plan to concentrate on the issues affecting people in the midst of a major life transition, such as:

  • Planning for retirement,
  • Going through a divorce, and
  • Becoming a widow or widower.

Thank you for reading and sharing our articles and please keep sending your feedback.

AND NOW, the top 5 articles of 2021, in descending order:

#5 Retirement Planning for widows and widowers

This article was bittersweet but also incredibly rewarding because it allowed me to share both my experiences but also my knowledge of retirement planning.

The death of Mary meant the loss of my best friend and the end of many of my retirement plans and goals. I began worrying about my new retirement reality, yet as more time passed, I realized that developing a new retirement plan was part of the healing process.

This article allowed me to share my four-step process to help widows and widowers calculate their new retirement pension and take a positive step forward on their own. Learn more about retirement planning for widows and widowers. The team at Dri Financial Group is always available to help.

#4 The importance of estate planning after a divorce

Our lives don’t always go according to plan, that is why it’s necessary to review your estate plan after significant life changes. I wrote this article with four factors in mind: Wills, RRSPs and RRIFs, life annuities and insurance policies.

When a marriage breaks down, it’s important to re-evaluate your plan and amend who receives your assets in the event of your death. This article covered the importance of changing your plans and renaming your beneficiaries. This article was also an opportunity for me to highlight that the team at Dri Financial Group work closely with other professionals, such as lawyers and accountants to help protect your finances after a divorce.

Click here​ to learn more about estate planning after a divorce. The team at Dri Financial Group is always available to help.

#3 Why you don’t want to die without a Will

Having a Will is arguably one of the most important things you can do for yourself and your family. Not only can a Will legally protect your loved ones and assets, but it can also outline exactly how you would like your affairs handled after you have passed on.

With over 25-years experience as a personal financial planner, I feel that it is my responsibility to share my knowledge, so it gives me great pleasure when I can impart information in my articles.

In this article I was able to explain why it is important to have a Will and the five most critical reasons why you don’t want to die without a Will, which included:

  1. You decide who gets what, rather than leaving it in the hands of the provincial government.
  2. You decide who handles your affairs.
  3. You want to leave specifics about how your family is looked after.
  4. There may be others you want to provide for.
  5. You leave more for your beneficiaries and less to the state.

Discover more about why you shouldn’t die without a Will. The team at Dri Financial Group is always available to help.

#2 We started our retirement savings plan late; can we still catch up?

I’ve always been a man with a plan, and I like to break down those plans into bite-sized pieces, as it makes each part manageable. But, not everyone is as organized and it’s easy to let things slip for a few months, maybe a year or even 10-years.

This article was a reminder that it’s never too late to start a retirement savings plan, and it covered six major steps:

  1. Admit you have a problem.
  2. Prepare a retirement projection
  3. Track your spending and earnings
  4. Do you have a spending problem?
  5. Do you have an earning problem?
  6. Are your fixed expenses too high?

I love to give good news to my clients and this article was a good news story from start to finish. Click here​ to learn more about starting a retirement savings plan. The team at Dri Financial Group is always available to help.

#1 How to Live off your dividend income

We all want our last cheque to bounce, right? But until then, we want to be solvent in our retirement years, for however long that might be. My favourite article of 2021 explained how it’s possible to live off a dividend income in your retirement years, and how much is needed to accomplish this goal.

It’s generally recommended in financial planning that retirees save a pool of money/assets sufficient to fund annual withdrawals until their expected age of death. This article discussed the logic behind the Dri Dividend Growth Strategy and how it can help to ensure a steady income in your retirement.

I might be biased but it really is a good read. Delve into my Dri Dividend Growth Strategy. The team at Dri Financial Group is always available to help.

Final thoughts

2021 was certainly a funny ol’ year. I have my fingers and toes crossed that 2022 will be better for all of us. Take a little time to read my top five of 2021, and if you still have questions, call my office to book an appointment. We will help you start 2022 in a positive and profitable way.

In fact, if you have any goal in mind — big or small — that requires some financial planning, but you’re struggling with where to start, reach out to our team. We have the expertise and life experiences to help guide you to achieving your goals.

Contact us today to learn more about the options available to you. CLICK HERE.

Learn more:


The process of finding a financial advisor can be overwhelming. It is our job to make that process simpler and easier.

Dri Financial Group’s proprietary Wealth Navigator Process is designed with you in mind.

Its structured framework helps you make an informed decision and feel confident in our team and management practices before we get started.

We offer you a range of services from creating bespoke financial plans and providing investment advice to helping you take advantage of our investment models. If you would like more information on the Wealth Navigator Process or our team, call me any time at 416.355.6370 or email me at richard.dri@scotiawealth.com.

Beyond helping you manage your finances, we take pride in motivating, educating and helping you expand your financial literacy. We are here to answer any questions you have and to help you feel in control of your financial destiny.

If you are ready to dive deeper into your financial literacy journey, we have a wide range of free tools and educational resources available.

source https://richarddri.ca/dri-financial-groups-top-five-articles-of-2021/