Help, I’m Dating a Widower!

Posted by in dating after divorce, dating in midlife, love after 40, understanding men over 40 | 3 comments

dating a widower

Is it a good idea to be dating a widower? Or will he always be comparing you to his late wife? 

Dear Sandy,

I am 62-years-old, and back in 2012 when I briefly joined eHarmony, I met a widower. I did NOT know exactly how to handle him. I learned a great deal and hung in there, but it was quite different. Fast forward to last summer when I joined eHarmony again and voila—I met another widower. I went straight to my minister, who said I would be alright dating a man who has been widowed for approximately a year. (There are some widowers who get on dating sites after three or six months.)
Just last week when I revisited eHarmony, I met another widower who lost his wife 14 months ago after a grueling illness. We briefly interacted, and he seems interested, but says that he is only seeking companionship, not even thinking of marriage. He also said that he wanted to know if I would consider moving (he is four hours away from where I live), because he loves his beautiful home that he and his wife built many years ago. YIKES….

Do you have any experience on this subject? I have read everything I can get my hands on for the past few years and dating a widower is NOT for the ‘faint of heart.’
I can easily handle discussions about the deceased, but what time period is ‘REBOUND’ period? And what about my feelings regarding being uncomfortable in the former spouse’s bedroom? 
Thank you!

Help, I’m Dating a Widower!

Dear CR,
Thank you for your excellent questions about dating a widower. This is something that a lot of my readers can relate to. First, let me preface by saying that my dating advice for women over 40 is about principles, not rules. So please understand that there is no one-size-fits-all advice for dating widowers.

What you need to find out when dating a widower:

1. Was his marriage really great?
Many times, it wasn’t as wonderful as we imagine it was, and the loss is not as big as we think it might have been. So, you need to ask him about the quality of his marriage was. How do you do this? You might say something like, “I imagine you had a wonderful marriage”, and see what he says…
2. Was he a caretaker during his wife’s long illness?
When you’re a caretaker, it can be one of the most stressful undertakings. I witnessed my mother’s challenges while taking care of my step father during his struggle with Alzheimer’s. If he was the primary caretaker, he might have stopped feeling as close to her a long time before the loss. Or, the opposite—taking care of her might have brought him closer. Find out by asking in a gentle way. A simple, “Were you the primary caretaker?” will probably yield the response you’re seeking.
3. How self-aware is he?
Most widowers never stop loving their wives, but they are also open to loving again. If he’s had therapy and/or he’s self-aware enough to put the past behind him, he’ll be open to loving you. Alternately, there are widowers who think they’re ready to date and post a profile on a dating site. But when you speak to them the first time, they can’t stop talking about their late wife. Those men are obviously not ready to love you.
If you find a widower who is open and ready to love again, he’s someone to pursue.
If you find he’s still grieving the loss of his wife, don’t tell him HE’S not ready to date. State your own needs.
You could say something like, “I’m so sorry for your loss. It feels like we’re in very different places at this time.
Please listen to this radio show I did with an amazing widower who wrote a love story about his wife:
I steer away from adhering strictly to the ‘one year rule’ that your minister referred to. Even though a year seems like a good amount of time to heal, everyone’s different. My friend’s widowed husband just started dating after two years. And he still isn’t fully ready.

To sum up:

  • Ask clarifying questions.

  • Figure out if he’s emotionally available.

  • If he is, move forward.

  • If he’s not, move on.

And remember that a widower who had a healthy loving marriage could be the most loving partner you’ve ever had!

Photo: Flickr/Hartwig HKD



  1. I recently dated a widower. His wife, God rest her soul, passed away 16 months ago. I am 43 and he is 53, with 2 grown sons. We only dated for a short time but he is the most amazing man and I like him very much. He told me, just this week, that he’s not ready for a relationship as he is being consumed by guilt over me. He thought that he was ready but he feels like he is cheating. Thankfully, he is engaging with services to deal with his grief. My heart goes out to him in this situation and I completely understand his feelings. It’s normal. I have left it open for him to contact me sometime in the future, when he is ready. My question is, is this a waste of time? Will I always just be a reminder of a time when he was consumed with grief and guilt? He’s the best man that I have ever met.

  2. Hi Carol,

    Sometimes we date the RIGHT person at the WRONG time. In those situations, I suggest you move on and date others, and if you’re both single when he is emotionally available, it could work out. BUT…don’t stop your life as you wait for him to possibly be ready. You deserve a great relationship with someone who wants you as much as you want him.

  3. Thank you, Sandy. I appreciate your response.

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