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Dating A Still-Grieving Widower

A surprising number of women tell me the senior men they’re dating are thoughtful, attentive, even generous, but they won’t commit to the relationship because they’re still mourning the loss of their wives. In some cases, their loss is several years in the past.

When a spouse dies, widows and widowers must adjust to the unthinkable, but women and men don’t grieve in the same ways. In this numbing circumstance, men are definitely the weaker sex. Women are more resilient. How can that be?


Senior men were taught early on that males must overcome – or at least hide – their grief. Outward expressions are unmanly. Bereavement must be done privately. Women, on the other hand, have spent a lifetime developing woman-to-woman connections, and these relationships help them to eventually recover and go on with their lives.

Men mostly intellectualize their grief, so it’s hard for women to understand how men can remain in a grieving mode even as they seek new companionship. I recall a first (and last) date with a man that consisted entirely of a monologue about his wife. His list of her virtues was delivered in much the same way a professor might deliver a lecture. The man was stricken – so much so that he seemed barely able to understand where he was and why he was with me.  “You’re not ready to date,” I said, as kindly as I could. “I guess not,” he agreed. We parted, our Starbucks lattes only partially consumed.


Because sympathy from men friends often comes down to, “stiff upper lip, dude,” a widower may gravitate to a sympathetic woman for support.  The woman may hope these therapy sessions will turn into something more, but too often they do not. My friend Estelle spent many long hours with Sam, a widower whose gratitude she mistook for ardor. This guy’s bereavement seemed deep enough to keep him grieving forever, but a mere eight months after his wife’s death, Estelle was stunned to receive a wedding invitation in which Sam was named as the groom.

Understanding the way senior men grieve is important at our stage of life. We need to guard against impatience. We need to remember that it’s wrong to tell someone how to grieve and for how long. It’s not a good idea to push a senior man to share his feelings. It’s no good telling him that swearing at the computer, kicking the lawnmower, and going to the movies alone are wrong ways to act. The way he processes his grief is going to be foreign to you.

To understand male bereavement it helps to look at why it’s different from yours and mine.

Widower: Home is a place where his wife tended to his needs. Without her, it’s an alien environment. Minus her sighs and laughter, TV is a noisy intrusion. Without the tap-tap of her computer keys in the background, he finds it difficult to read. The soft, muted hues of the living room carpet are reminders of her impeccable taste.

Widow:  Home is her inspiration and her favorite workspace, even if she has a career. The decoration scheme is hers. Her flower garden is a source of pride. She makes coffee in a French press. When she feels anxious, she cleans out the coat closet, or creates a beaded bracelet for her granddaughter.

Widower:  He knows few people in the neighborhood, his acquaintances are mostly people in his work circle. He golfs regularly and plays cards twice a month with a group of men from his sports club, but they stay clear of conversation about his grief.

Widow:  She belongs to two book clubs. She teaches English to new immigrants. She eats strawberries and M&Ms and stays up late to finish power-point presentations. She meets friends for lunch and is not ashamed to shed a river of tears in response to their expressions of sympathy.

Widower:  He has a hard time with solitude and begins to think about companionship. He has not been with a woman other than his wife for decades, and he regards sex as a central part of a successful relationship. He worries about his capacity for satisfactory performance. He wonders if he will be able to make love to a new woman without guilt.

Widow: She wants to be part of a couple because the world seems colder to singles, especially senior women. She craves help with financial decisions, household chores. She wants to plan vacations with someone. She thinks about sex and hopes the man she ends up with will be proficient as well as sensitive. She believes her late husband would want her to find a protective male.


Men distrust their feelings, while women know there’s nothing we can trust more. When a bereaved man decides to seek a new relationship, he will want it to be with a woman who will honor his past, just as you want him to honor yours. Entering into a relationship with such a man takes more than patience. It also requires an ability to evaluate his feeling for you.

  • Let it not be sisterly.
  • Let it not be for the sake of expediency.
  • Let it not be for testing that his sexual prowess is still operative.
  • Let it not be until-the-right-gal-comes-along.

If it’s any of these things, your chances are slim.

Ask your widower – directly and without impatience – if he’s on the way to commitment. If his answer is vague and you don’t mind staying on the periphery of his life, you’ll stick around, telling yourself that you’re acting honorably, supporting a guy who’s making his way through a hard time. Sometimes being a helping, supportive part of his life pays off. But after months or years of investment with little return, it’s time to evaluate the value of remaining in the relationship. If you hang around — and you nag — you may lose more than time (which is extra-important at our time of life). You could be left with nothing but some shredded dignity.

Make your departure a graceful one, and tell him kindly that you’ll be glad to hear from him when he’s ready for the mutuality that is the mark of a genuine relationship.

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'Dating A Still-Grieving Widower' have 53 comments

  1. December 5, 2016 @ 6:00 pm Sienna

    Steve — Thank you for sharing this beautiful tribute to your wife. May happy memories of your years with her help you in this sorrowful time. Your story helps our readers, most of them 60-plus women, many of them widowed, to see a man’s point of view, to empathize as he tries to come to terms with the loss of someone so very dear to him. Thank you for giving us this opportunity for insight.

  2. December 3, 2016 @ 7:25 pm Steve

    My wife of 38 years died just 2 weeks ago. She battled cancer for 8 years. The last 18 months I was her caregiver as she could not get up an could barely move. Being a caregiver was the most heart wrenching , stressful and hopeless thing I have ever done. Seeing her suffer and being able to do so little. We had a great marriage. She was everything a wife is supposed to be. People called me a hero for the effort I put into her care. It really was 24/7. But I just told them she would do the same for me. And she would have.
    I always knew I would lose her. They gave her 5 years. She made it 8 years before the pain and nausea was just too much and she gave up.
    During the 8 years, I rarely let myself think about the future. As a caregiver, I was too busy and too involved to let myself think about life without her. There were times when I would get overwhelmed with stress and feelings of being helpless and I would sneak out to the garage to let it out. I didn’t want her to see me suffering. She had plenty to deal with already.

    Now she is gone, our home is empty. The hardest part is not having her here doing her crafts or making stuff/outfits for the grand kids. She loved the holidays.

    I am more geek and dweeb than anything else. She was melt your heart beautiful and was also a very small woman. Guys would look at her and be smitten and look at me and be really confused.

    I am a mess most days. I cant stop crying. Its like every memory of out time together before the cancer just makes me cry. Little things do me in. I can keep a straight face and get things in order but inside there is no order. I have thought about will I ever be with someone new? Would finding another woman “fix” all of this. I sort of know the answer. I would most likely get my heart handed to me and have to come home to this empty home and just ball my head off in sorrow that I lost the best thing that ever happened to me. I wish I could at least stop crying for just one day. I have lots of friends and family. Our kids come over regularly.

    But its not the same. The love and the affection and the feeling that it was her and me forever is gone. I feel so very alone. My world is upside down. I am going to attend a grief group session at the church. I don’t go to church but I need a little help trying to keep myself together. I have already told anyone who will listen that if they get there before me, warn God that I am coming and I am a little pissed. I may start in heaven but will likely be kicked out in short order.

  3. October 3, 2016 @ 10:13 pm Recent Widower Dating

    […] Dating A Still-Grieving Widower | Dating Senior Men – Entering into a relationship with a widower who may still be grieving takes patience. It also requires the ability to objectively evaluate his feelings for you. […]

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