Question Three: Is Dating a Widow a Losing Proposition?


Quinn asks:

“Dating a widow. I always felt that since the relationship never ended with a ‘break up’ that there was no real closure, and therefore the presence of the significant other would persist indefinitely. Is that true? How’s a guy to compete with a potentially perfect guy that’s no longer around?”


Dear Quinn,

Whether a new man remains “in competition” with a perfect, but absent, partner depends on the widow. A widow who has had enough time to heal and adjust will have gone through her own closure process, whatever that means to her.   She will be ready to have a new relationship.  I know several widows who, within a couple years after their husbands’ deaths, wanted to date again and to have new experiences.

After the loss of a spouse, there is no set amount of time to wait before moving on.  Wall Street Journal article  It just depends on the person.

Also, just because our spouses died, does not mean that we idealize them.  I know many widows who are aware of their late husband’s faults or of issues in their  marriages.  Part of grief counseling includes looking honestly at the past for clues about what we want in our futures.   And many marriages that ended in death were still bad marriages.

Furthermore, widowed people in new relationships can still love, and at times even miss, their  late spouses without taking away from their current relationships. Carole Brody link   They can move on from having been in one marriage to a subsequent committed relationship, incorporating both into whom they’ve become.  Michelle Steinke link.

But, there is a risk that the lovely widow in question is not yet ready for a new relationship.    Signs are constant references to her late husband or repeated expressions of regret about her life without him.   Or maybe she just seems really sad or withdrawn.   In that case, your concerns are well-founded.  If so, address the matter with a gentle, nonjudgemental query about whether she is ready to move on from her past.

Many people are haunted by the specter of their partner’s “lost love” who embodies all the things their mate finds lacking in them.   Similarly, a divorced person may still compare their new prospect to their prior, now idealized, spouse.    As we get older, the people we date are likely to have had past partnerships.  The question is how each individual has integrated their pasts with their current selves.

A widow can have “closure” on  her prior marriage.   It is part of the grieving process which, ideally, leaves us strong enough to move on.  But, it is unrealistic to think the widow leaves her memories behind never to be spoken of again.   They will always be a part of her life. Dating a widow who has healed is being with someone who had the capacity for love and can access that capacity again.

There is no competition, just “then” and “now.”










  • Michael says:


    Rather helpful response to a question that has occurred for me as well.
    I do believe that your response is valid for a divorced person as well — people require different recovery periods after the death of a marriage just as they do after the death of a spouse. I suspect the same could be true of dealing with any loss such as an unmarried person who lost a partner (death or otherwise) after a long term relationship. The circumstances and situations which occurred during and after the loss impact the recovery time.

    I believe many hope to date using hard fast and set rules, i.e. “a person needs to eschew dating for at least one year after a divorce.” In the process of abiding by these “rules” excellent opportunities might be missed — potentially very rewarding opportunities. Not all “eligible” women and men are cast from the same die. Thus there are no set rules.

    Being receptive to the feelings, statements, behaviors of others is vital to establishing a successful relationship. That statement goes beyond merely treating others as you would like to be treated; it means treating others as THEY want to be treated.

    Best of success to you and your readers,

    • Debbie says:

      Excellent points Michael. I have found a dearth of people who get that we should treat our prospective partners as they wish to be treated. Have you considered your own advice column?

  • Jake says:

    Quinn’s concern about dating widows is not just a guy thing. Based on my experience, women are just as wary of a “Losing Proposition”.

    There are many types of widow. The Hungover Widow lost her husband to cancer. My wife took her life after a decline lasting several years. She was desperate for relief from her suffering. Our marriage was quite good but not perfect. I initially was extremely angry at her for the choice she made to “leave” me and our children. I still struggle with issues of forgiveness and survivor’s guilt, but the sharpness of the loss has faded with time, and I have always been a silver lining-type person. I am grateful for the many blessings in my life including our children, family and friends.

    In the 2.5 years since her death, I have dated some and been in 1 serious relationship. The biggest challenge has been the reaction of each of my potential partners to the manner in which I lost my wife. Divorce is bad enough, death is worse, but suicide is seriously disturbing and seems to raise huge red flags. No matter how much closure I feel, no matter how happy and outgoing I feel, the women I am attracted to tell me that something must be wrong with me to be able to move on after such a tragedy.

    But really, what choice do I have? I want my children to have a positive role model for living and loving and moving past the darkness that we all share.

    Please give us widows/widowers a chance!

    • Debbie says:

      Dear Jake, I am so sorry for your loss. And I am sorry that you have found telling potential partners about your wife’s death to be so hard. I do understand that you would be ready to move on and experience joy again. It’s wonderful that you feel that way. I truly wish you luck in finding someone who appreciates what you’ve been through and how that reflects positively in so many ways.

  • Paul says:

    Great advice and I agree with almost everything. However, I think asking someone if they’re ready to move on isn’t the most productive way to go.
    I’m a widower myself and have been for many years. But it’s only in the last year or so that I’ve been “ready to move on”.
    I was certain that I was good to go about a year after my late wife died. I now feel that at that point, I didn’t even have the basic idea of what it meant to be ready to date. It’s not just about handling sadness and grief, it’s about having your new social system up and running, all of your financial issues figured and under control, your children stable, and your own physical and mental health robust. And probably much more. If those things aren’t working, then it’s difficult to be a great partner.
    Observe for yourself and form your own opinion on their state of readiness. Then, if you think there’s a problem, discuss it with them and help them move in the right direction. If that’s not possible, then consider whether the relationship is right for you.

    • Debbie says:

      I’ll defer to Paul on judging whether the widow or widower in question is ready to be in a relationship. Excellent advice.
      I too thought I was ready to date when it was probably too soon. But I did date before I had my social system in place. (I’m still working on that). And before I was at my mental best. (Still not there yet).
      I think it can be too limiting if we have to wait until everything else is in place, although of course it depends on the individual. But a good relationship did help me to make positive changes in other directions as well.

  • non-lawyer says:

    “But I did date before I had my social system in place. (I’m still working on that)”

    What is a social system for dating?

    Grief is a universal emotion. Certainly an issue when a spouse dies. But for someone who married very young, and lost a spouse in mid-life, I think they must find their own identity as a individual person. The person may decide they have a capacity for solitude, and remain alone.

    Also, a women may not need a man after 55, see

    Are Women Done With Men After Age 55?