Tips for People Dating Widows and Widowers

My five Personal Pointers for dating someone who lost their spouse.

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, they will be able to love two people simultaneously. If you’re wondering, I mean their late spouse and new partner.

Now that I have reasoned that, I can 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.

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

Please 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.

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

  • Let them grieve special anniversaries.

I’m not sure if this will change, but for now, I take time off to honor and remember special anniversaries such as Mary’s birthday, our wedding anniversary, and the date of her funeral. These days will always be filled with 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 some dates induce memories and feelings of sadness and grief.

  • Children.

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

As many of you know, I have three children. Their reactions were mixed when I shared my dating plan with my adult kids. 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.

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 observation would be to treat their kids very carefully. Don’t try to become their new parent.

  • 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, homes, 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.

To minimize financial conflicts, I believe the “money” discussion should be had very early on in a new relationship. My assets are mine, her assets are hers, and if we buy anything together (like a house), it’s “our” asset. Upon my death, my children will inherit my assets (the same applies to her assets), and all joint expenses will be shared equally or as per a mutually agreed plan.

  • Take it slow.

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 be impatient occasionally.

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 I can’t or don’t want to be loved again by another woman.

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 [email protected].        

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One response to “Tips for People Dating Widows and Widowers”

  1. Paul Greene Avatar
    Paul Greene

    This is very helpful, Richard ! I would add one note of interest to me. I too have developed a new relationship following the death of my spouse of nearly 60 years.
    It is a deep and wonderful relationship. Occasionally (usually when we are busy or in a hurry) we will call our new lover by our former spouses name. It was embarrassing for a while until we ultimately realized it was a compliment in disguise. We’ve talked about it and chuckled about it a lot. Valuing the love of your former spouse is important to share in this new relationship ! Paul Greene


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