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What If He’s Still Grieving?

If you’re over 55, you’ve probably lost someone who was dear to you. If you’re in your sixties or beyond, chances are even greater that you’ve lost a parent, a sibling, a close friend – or (most devastating of all) a beloved spouse. The same will be true for almost any senior man you will be dating.

Only when I stopped to count them did I realize how many women I know who are dating grieving men. These women are variously hopeful, dejected, or angry, but mostly they are patiently waiting for things to change. For the lucky ones, grief will become more manageable and relationships will begin to expand. The unluckier ones will find that the grief lasts forever, and meaningful bonding will never take place.

How do we tell the difference between a hopeful situation and a discouraging one? If you’re dating a grieving man, you’re hoping your sympathetic response to his sadness will cause him eventually to see your real value. You’d best balance that fantasy with reality. Kindness does beget kindness, but it doesn’t always lead to being chosen as a cherished full-time companion. You can maybe avoid being hurt if you confront — with honesty — these difficult questions:


After the death of a loved one, some people find it harder than others to resume a healthy and constructive lifestyle.  Grief counselors won’t put a time limit on bereavement, but it’s clear that after a certain point, grief can descend into depression. Here are a few things to watch for:

  • Frequent (many times, most days) references to his departed
  • Shrine-like photo displays in most rooms of his home, most especially his bedroom.
  • Excessive emotional dependency on his children and grandchildren


If your man is unable to fully enjoy a restaurant dinner, a movie, or a stroll through a museum, if he shows no interest in the music, sports, clubs, or family events he used to love, your sympathy and generosity of spirit will not be enough to change him. In fact, you could be doing him harm by throwing him an emotional lifesaver that keeps him just above the surface of a sea of despair. The inability to return to the real world and enjoy its bounty is a sign of deep grieving. Steer him (gently) to a counselor.


When her good friend Suzanne died, my own friend Gail became a much-needed support for Suzanne’s husband. He found comfort in speaking about his loss with someone who not only loved and revered his wife, but is also a professional therapist. It turns out that a PhD in psychology is no shield against hopeless desires. Gail opened herself to painful rejection when she began to imagine herself an object of this man’s growing affection instead of what she actually was – a crutch, a prop, with just a bit more significance than his collection of biofeedback CDs.


His wanting to DO things is the best sign. An eagerness to spend time with others is a sign that healing is taking hold. The return of sexual desire is especially significant. For some widowed men, first attempts to have sex after losing a beloved partner are a source of shame or guilt (“Am I betraying her?”). These feelings can lead to temporary bouts of erectile dysfunction.  The good news is that a man who can acknowledge a desire for sex is most likely on the road to recovery. Your response (serene, composed, and encouraging) will determine how things go from there.

Each of us experiences grief in a way that is utterly unique (click on this summary from the website). With a reasoned and understanding approach, you can help your senior man embark on a new phase of his life that is contented and fulfilling.



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'What If He’s Still Grieving?' have 10 comments

  1. September 22, 2014 @ 10:17 am Port in a storm

    This hits home for me because I think I’m with someone who is on the road to recovery. We have been together for almost 4 years and the grief has been constant until recently. I have tried to be supportive and I think he appreciates that. I really appreciated reading this because it’s encouraging to think all my patience will pay off.

  2. August 2, 2014 @ 6:32 pm Lee Murray

    Well, I have been left behind by Sam, our sixteen year old Basset hound in January. My wife died in March. I believe what everyone says amounts to giving and giving and giving.

    Life is so short!!! – Lee murray, Keizer, Oregon

  3. May 6, 2014 @ 9:48 am EGarth

    I’ve just come back to this post after reading it once before. It gave me a lot to think about because I was dating a grieving man. I don’t think I was very sensitive to his grief because he was trying to hide it. When we did talk about it he seemed glad. Thanks for making me think about these things. It was very helpful.

  4. November 24, 2013 @ 1:44 pm Sienna

    Byron – Thanks for your comment. Grieving may never go away. It’s how we handle it that counts.

  5. November 23, 2013 @ 2:26 pm MLGarner

    I dated a man who acted just fine unless some little thing went wrong and then he acted like I was intruding on his space. I wasn’t comfortable in his home because as you say there were shine-like photo collections all over the place. I am a divorcee so I can’t relate to someone wanting someone back, but I tried. Now I see it was a waste.

  6. November 23, 2013 @ 1:43 pm Sienna

    Idaho Girl — A friend of mine told me she had solved a problem like this by saying, “I’m flattered that you’ve chosen to share your feelings with me, but it seems unfair to us both for you to speak only about your situation. I’m an interesting person too, and you might enjoy our relationship more if we shared information more equally. Let’s agree not to see each other until you’re more ready to date.” This caused the man to think about the one-sidedness of their relationship and to change, and they’ve continued to spend time together.

  7. November 23, 2013 @ 1:15 pm Idaho Girl

    People need to get over grief and get on with their lives. It’s not fair to ask someone out and then bend their ear with stories about the dear departed. I’m through being a counselor andI want real companionship. The next guy I date will be divorced. I’d rather hear complaints about bitchy ex-wives than worshipful stories about a dead lover.

  8. November 23, 2013 @ 12:23 pm Abigail

    I was widowed six years ago. I met a man with this kind of sadness and I gave it my best shot, after which I just had to walk away. He just kept comparing me to her, and I felt he didn’t know who I was at all. I don’t say he’s a bad person, just kind of confused and I guess terminally unhappy.

  9. November 23, 2013 @ 11:17 am Byron

    The right woman can take a man out of himself for a while, but the grieving comes back.

  10. November 22, 2013 @ 3:11 pm Tracy

    I read your other posts earlier about widowers. You have a sensitive point of view. Thank you.

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