Dating for Widows and Widowers: 5 Questions to Ask Yourself if You’re Ready to Date

Widow Dating as Stuck in Reeds

Stuck in the Dating Thicket

I rushed into dating far too quickly after George died. I tried dating a couple of guys only a few months after his death. I waited 14 months before joining an online dating site, but it was still too soon, at least for me. I could have saved myself a lot of pain by waiting longer.

Let’s try some introspection before we start dating.  So, here are:

Five Questions to Ask Yourself Before You Start Dating:

1. Have You Regrown Your Shell?

I started “beta-dating” a few months after my loss, thinking I’d start practicing. But I was still too wounded and vulnerable, making me needy. If my date cancelled or wasn’t available, I was plunged into despair.

I needed companionship NOW, which meant I needed it too much.

Plus, dating comes with rejection and criticism. I dated a couple guys who wanted me to change to meet their needs. Now, I’d laugh (albeit huffily) and move on. But one year into my loss, I worried, “What’s wrong with me? Why can’t I make this work?”

If someone doesn’t recognize your wonderfulness, that’s their problem. But when you’re feeling super vulnerable, being rejected is devastating.

If your sense of self is still forming, it’s not time to date. Far better to spend your time with friends who will buoy you up as you figure out who you are in this new world.

2. How’s Your Energy Level?

The first year and a half, even two years, after my loss I was often exhausted. Part of it was bureaucracy and dealing with deferred maintenance, but part of it was having been through such a traumatic loss.

I severely underestimated the toll of having been George’s caregiver. I needed to spend what energies I did have taking care of myself.

Having only the best intentions, George’s parents took me on a three week cruise of the Baltics four months after he died. I sleepwalked through much of it, too tired to enjoy the fast-paced sightseeing and being out of my comfort zone.

Similarly, 14 months after his death, I found traveling to meet dates and figuring out new locales to be enervating. I lacked the energy to enjoy trying new experiences. Try some long days out with friends before attempting any lengthy or faraway dates.

3. Have You Processed Your Loss Enough to Focus on Someone New?

This is a hard one because you might not know until you try. I tried dating a nice Jewish yogi lawyer (just like me) four months after losing George. But I was lost in my memories. Everything we did reminded me of something George and I had done or eaten or seen or hadn’t had the chance to do because his life had been cut short. I was fighting back tears on almost every date.

I also had a lot of guilt over having been George’s caregiver. I hadn’t yet forgiven myself that he died on my watch.  I lacked closure. Until I resolved my own issues, I couldn’t be present for someone new because I was still living in the past.

I got through the guilt with grief counseling and journaling, but I wasn’t ready to date until I’d put my ghosts to rest. Trying to date before I’d processed George’s death caused unnecessary turmoil both for me and the guys I was seeing.

4. Do You Even Want to Date?

“Have you met anyone new yet? No? Well, get out there! You’re still relatively young and healthy!” Haven’t we all heard this from well-intentioned people who are uncomfortable because we’re alone.

Yup, time to hit Target and pick up a new spouse now that the old one’s gone!

But we may be happier on our own. I hear from so many widowed folk who get plenty of love and companionship from friends and family. They don’t want to re-enter the dating fray.

Yet the societal benchmark for recovery seems to be seeing someone new. I drank that koolaid as a new widow, but finally realized if I don’t want to date, it didn’t make me any less “recovered.” It also didn’t make me any more or less attractive.

It’s hard for me to admit I was using dating to prove I was still wantable. I confused being liked with having self-esteem, but that comes from within.

5. Do You know What You Want?

This last one is more for the benefit of your prospective beaus. I didn’t know what I wanted when I started online dating. Being a nice girl, I sought a stable guy to settle down with. But I really wanted to be on my own and meet different kinds of people for awhile. I unnecessarily confused a few serious guys who wanted exclusive relationships,

One fellow wrote me that after he lost his wife, he wanted a friend with benefits only. That was his emotional bandwidth. Another gentleman said he wants a girlfriend, but still wants to live separately. (I’ve come to see his point). It helps to have a goal before shopping in the human mall of online dating.

So, what helped you to decide whether or not you were ready to date again after being widowed? How did you reach your decision? And if you’re not ready, how will you know when you are? Blogging has shown me older daters are a cynical lot. Success stories and words of wisdom help us all.
























  • Michael Ivers says:

    Thank you Debbie, again, for your thoughtful and thought provoking post.

    Your comments and suggestions are relevant to all who date for the true purpose of possibly meeting that man or woman that suits each of us so very well.

    We should each perform the same assessments as you mention, especially numbers 5 and 4 (in that order in my opinion).

    My best wishes to you this holiday weekend,

    • Debbie says:

      Thank you Michael. I agree on your order. And a great holiday weekend to you too.

  • Kerry says:

    I waited a year to begin dating. That seemed like a reasonable time frame for me after having been with him for 25 years. I read a formula in one of my grieving books that said for every 5 years you were with your mate, expect 1 year of healing. I’m 6 years out now from the trauma, and still not fully over it, but beginning the dating process when I did, and continuing to date has helped me push through it. Dating, or being with someone exclusively, takes the focus off the loss and puts me more in the present and in a hopeful future.

    • Debbie says:

      Wise words from a fellow yogi. I admire how you check in with yourself throughout the process. (Miss you).

  • suzanne says:

    A very timely post for me. I entered my recent second year anniversary as a widow after 25 years with a list and desire to start dating. The list included #1 widower, #2 healthy, #3 – 10 all the standard stuff. Well my list quickly became irrelevant as I started dating and realized 1) the pool is small, and 2) widowed and healthy men aren’t necessarily the bomb either. A friend said to me “I wouldn’t want to date someone at 50 that didn’t have a story. Everyone has a past and divorce isn’t always a bad sign”. I thought that was good advice… my bias was that my marriage didn’t fail – we worked hard at it and were successful… and then he died. And I also went through a succession of dates that made me question everything – from the size of my nose, to my readiness, to my life choices. I never questioned any of these things with my husband. It wasn’t until I looked at a man who was a friend, for a long time, with all his imperfections and decided his imperfections and my imperfections just may make a perfect relationship. So we are two months in… who knows… but I know I’m stronger because I dove in. And I read a lot of blogs hahah. Love Suzanne

    • Debbie says:

      I went through the same thing when I started dating and wound up questioning my life choices, how I spent money, etc. I too hadn’t questioned those things when I was married. I admire your flexibility and willingness to change your criteria. Also, a willingness to dive in. Great story.

  • Lisa says:

    I lost my husband 2 1/2 years ago very suddenly as a result of a heart attack. We were both in our mid-50’s and I guess I wanted to get back out and find another companion quickly before I got ‘too old’, so I started seeing other men about 6 months after he passed. This was a mistake because I hadn’t recovered from his loss yet.
    I dated several men who were nice and interested in relationships with me, but one stated that I was ‘cold and emotionally unavailable’. He was right, so I took myself off the dating market and now I am not so concerned about getting older and being alone.
    If I don’t ever meet the right person then I am okay with that. I really need to process my husband’s passing first, no matter how long that takes.
    I was targeted by some younger (40’s) creepy men who thought that I would be desperate enough for attention that they could take advantage of me, but I was smart enough to see through them. I need to be okay with who I am at any age.

    • Debbie says:

      Good for you for recognizing the creeps. I briefly dated someone I decided was using me bit financially and I ended it. I too feel less worried about being alone the more I recover and feel comfortable with myself. I see life more in stages than absolutes.

  • Joanna says:

    I have been a widow for just over 2 1/2 years. I knew my husband was terminal when I married him in 2008. I was frozen after his death–some caregiver guilt, some omgosh, I don’t know how to do life alone.

    I recently said to a divorced friend of mine, when she expressed dissatisfaction with the single life, that I didn’t care if I ever had sex(or a date) again, and that it would be that way until I met the one who changed that tune. I am not Diogenes, looking for a good man with my lamp. I am happily, busily, gratefully on my own, getting to know myself, addressing my needs as I perceive them. And having the best life I have ever had.

    And I say this though my husband was a huge treasure in my life, a recognized gift. I am grateful every day that we met, loved and lived together. I just have no interest in replacement–don’t know if I ever will.

    Good and thoughtful piece, thank you!

    • Debbie says:

      Thank you for your thoughtful comments. I too am getting to know myself and my needs, in some ways for the first time. I love the way you gracefully appreciate the different stages of your life, both married and on your own.

  • Barry Neal says:

    Well said. Thank you, Debbie.

  • E. says:

    I too began dating soon after my husband died. I was lonely, bored, wanted to get out more.

    Lots of disasters, lots of fun, met some interesting guys along the way…

    Now, five years later and I’ve fallen in love with a guy. We’re talking about marriage.

    What has surprised me is that I began having anxiety attacks soon after we began dating. I’m also peri-menopausal.

    I’m not sure if the anxiety attacks are symptoms of peri-menopause or related to fear of re-marrying and thoughts of becoming a widow again. After all, we’ll all die some day.

    It’s difficult. There are days when I snap at him, days when I cry lots, days when I can’t eat.

    I’m trying meditation, essential oils, yoga.

    Good luck everyone!

    • Debbie says:

      Really difficult to analyze. I’m a yogi trying to get more into meditation, so I think you’re trying the right things. Wonderful that you’ve found love. I get anxious too, also peri-menopausal and can’t target the cause sometimes. Breathe deeply. Take care of yourself. 💕

  • Stephanie says:

    This is an excellent blog post and also quite relevant advice for anyone who has just ended a significant relationship

  • Julie says:

    It has been almost two years, since my sweet husband passed away from cancer, we had been together since 1987. This post on dating got my attention. I have not even thought about dating until last week, I met this guy who I thought was interesting, so I give him a call, most awkward phone call ever, let me just say I don’t know how to tell someone that I’m interested in getting to know you…so weird, Didn’t work out so well for me, as he told me thanks but I have a girlfriend, don’t think I’ll be trying that again any time soon. I so miss my guy……

    • Debbie says:

      Dear Julie, Trying to navigate dating or relationships when we’re older seems to be an exercise in awkwardness. And even when it isn’t, well, it’s uncomfortable several months later. I too miss my guy with a blinding pain.But I so appreciate that you stopped by to visit and comment and say something that I so relate to. Love.

  • Betsy says:

    Excellent post. It has been sitting in my inbox, just waiting for me to answer. So much to say, but I will spare all that now. I do appreciate your list, and the comments from the others.

    I need to take care of me first. If it is meant to be, then I would be willing to meet someone. Companionship is what I miss the most, as well as intimacy. Not just the sex part, but the parts that come with knowing and loving someone for so long.

    Thank you for the post.

    • Debbie says:

      Thank you Betsy. I so appreciate your positive comments on my writing. I so agree with missing the sense of knowing and loving someone in a depp way,