A Widow Finds Love through Perseverance

My Instagram Post with tags “#SecondChapter” and “#InLove”: What mushy optimist posted this drivel?

I recently got an email from a widow of fourteen months who asked if it’s okay to fall in love again?

Hell yes! We deserve love and we deserve to be in love. I wrote about that here.

I just didn’t think it was possible for single people over forty. We carry too much baggage. We’re too idiosyncratic, too entrenched in our ways. We don’t want to disrupt our lives. We want our meals and our rooms just so. Our schedules are sancrosanct.

But then, I found my person. Actually, he found me.

In  September, I was again trolling through my OK Cupidity messages when I got one that said, “We’re both culturally Jewish, nonreligious lawyers who are looking for a relationship. We live ten minutes apart. Do you want to talk?”

”Sure,” I typed back. He turned out to be awesome. He still is.

I’m no longer a cynic. And I may be out of weird dating stories. (Almost). But not advice.

I wish I could say I did something miraculous to find my guy, but I just hung in there, staying online (I even tried Coffee Meets Bagel), answering messages, going on dates with promising people, and smiling so much I thought I had fishhooks embedded in the corners of my mouth.

I hung in there even when I didn’t believe the right person even existed. Prior to meeting my boyfriend (who I hope isn’t reading this) I was dating a polyamorous doctor with a Wharton MBA who’d abandoned both medicine and business to become a tantric sex instructor. I didn’t see it as forever–more like a weird field trip—but at least it was interesting while I kept up my search.

The best dating advice I’ve received:

There’s a reason all these people are single.

But there are good guys out there. The men who’ve commented on this very blog have been thoughtful and perceptive even when I’m verging on man-bashing. I joined a hiking group on Saturday mornings and there were several articulate, nice, apparently available, guys, including a few widowers who described their losses with real depth. (It’s the Hike On! group in Meetup.com).

So, my very best piece of dating advice:

You are going to want to I've up. Don't


If I’d given up when I was getting sick of the process, when I was getting messages from the disturbed, when I was sick of rejecting and being rejected, I never would have met my current boyfriend. And once I met him, even on our first date, I knew I was done. (I even agreed to dinner instead of coffee for a first date).

My second best piece of advice:

Do Not Settle for Less than You Deserve.

I learned this the hard way after dating the emotionally abusive guy I’ve talked about here.  I wasted a lot of time dating guys I was never going to have a future with. (Being a writer, I could call it research). George was my high school sweetheart, my one and only. For a while I was looking to have experiences since I never had them when I was younger. But later this year, I wanted to be in a long-term relationship.

What helped me to figure out what I truly wanted was making list of the qualities I sought in a man. My friends had said to do this, but I ignored them.  It wouldn’t change who I met. But it did change how I filtered people out.  Here’s my list:

Debbie’s Guy:

  1. Can be a grown up if necessary
  2. Gets my sense of humor
  3. Good with time apart
  4.  Wants to travel
  5. Socially appropriate and articulate
  6. Non-workaholic
  7. Emotionally available and affectionate
  8. Quiet about former partners
  9. Positive outlook
  10. Financially stable

The list grounded me when I got caught up in messaging with someone who wasn’t right for me. I just think a guy over fifty shouldn’t be living in his adult kid’s basement. Even if he is really cute.

So now, I’m trying to be more positive. I’ve stopped prefacing all my sentences to my new boyfriend about the future with “If we don’t break up by then.” Then he can stop prefacing his future plans to me with, “Stop being so negative.”

I feel a sense of possibility. I even cleared out my spare room of all the excercise equipment I no longer use. So, now it looks like this, empty and open to something new:

Debbie's Empty exercise room with Billy Idol poster

My Empty Room

So that’s what I want for all of us this season: a sense of possibility and expansiveness, in all areas of our lives. Tell me what you want for the new year, or ask me your dating questions. (Hell, ask me anything, it’s lonely being a writer), in the comments below.



P.S. I was so surprised and grateful that Feedspot listed my blog in this list of top 50 blogs for widowed people.




  • Quinnland23 says:

    Woot!! I’m so super happy for you! I will definitely hold to your example of perseverance. And I finally understand the reference to ‘Coffee Meets Bagel’! =P
    Now you should have buckets of material on navigating a new relationship as fully formed independent individuals. For example, how do you keep an active connection and a romantic spark when life keeps you on separate schedules?

  • Suzanne says:

    Ah happy formyour news! I just broke up with Felix Unger – my rebound guy after Oscar the slob. My husband of 20 years was the perfect combination of the two and these relationships both almost killed me and made me sweat of dating forever!! Ugh! My question is…. when you lose a spouse you lose your “witness” – that perso. Who knew and loved all your flaws and imperfections too, knew your story. Do you just decide your story doesn’t matter anymore? Or do you drag them through every chapter of your life so you don’t lose yourself too?

    • Debbie says:

      Weird coincidence. I’m just writing something about letting the grieving talk about their lost loved ones instead of shutting us up because it’s “sad.” At a recent party when people were giving marriage advice, no one seemed to want mine. It’s like my 32 years of togetherness didn’t count because he’d died.

      Yes, your story does matter. It’s part of who you are. You don’t let it go. I haven’t let my story go. I hold it with love. I share pieces of it when I think it’s applicable or I want to get closer to someone. I don’t think it’s a matter of dragging your late spouse with you, but of compartmentalizing. It’s a cherished piece of yourself to share when you choose. I just hope you meet people, men and women, worth sharing your story with.

  • Therese says:

    That is wonderful that you found love again. I really like the idea of making a list of desired qualities and not deviating from it. I may borrow your list because those are traits I value as well.☺ It is draining to meet so many men for coffee and feeling no emotional connection. It is tempting to throw in the towel, but you have reminded me that love can be serendipitous. The feeling of happiness and hope in your voice is contagious. I hope you have found your second soulmate.

    • Debbie says:

      Thanks Therese. I hope so too. He is really sweet. I agree that all those initial meet ups are draining. Like doing a second job. And I hope your list leads you to something good. My very best wishes for you. 😘

  • Jean says:

    Hi Debbie –

    I’ve loved reading your blog and I have my own similar story.
    I’ve been widowed for 8 years. My husband died suddenly of a heart attack when he was only 44. We were together 20 years. I started dating about a year and half after he died. I was sure of two things.
    1. I was devastated and heartbroken (as were my teens).
    2. I still wanted a full, rich, wonderful fun life.
    I don’t think those things are mutually exclusive. In the past 6 years I’ve gone on over 50 first dates and have had a few semi-serious relationships. Oh, the stories! Earlier this year I broke up with someone I had dated on and off for almost 4 years. It was never the right relationship for me but I never thought that I would find something more meaningful at my age. I thought I needed to compromise a lot.
    Fast forward to this past August when I met another “first date” from OK Cupid (the only online dating site I’ve ever used). From date #1 I knew this one was different. We just clicked in a way that felt completely natural. I am 100% my goofy weird self with him and it just completely compliments his goofy, silly self. We are more compatible together than anyone I’ve ever met other than my husband. And the person I am when I am with him is my favorite version of myself, it that makes any sense.

    He is not the person I thought I’d fall in love with. In many ways, he doesn’t look like the picture I imagined in my head. And, that is completely okay, as it also turns out that you don’t necessarily know what was missing in your life until you find it. That’s how I feel, anyway. I met him a month after I turned 56 and I couldn’t be happier. So from another widowed middle-aged woman I just want to say, don’t give up. I can and does happen.

  • Debbie says:

    Thank you so much Jean for sharing your story. I think it will really encourage anyone who reads this post. I agree that we can be grieving and devastated AND want companionship and another chapter.

    Our stories are similar, down to OK Cupid. I too had to end things with an on-and-off, “not right for me” guy before venturing online again and finding the RIGHT person, someone I see a future with. So true about being ourselves and feeling comfortable with that. I’m so happy for you!!!!

  • Gary says:

    I am glad to see are finding happiness again. You look happy in your picture. It’s an inspiration to all of us who are wandering in the morass of losing our one true partner. This is the second holiday season since my wife died. Diane and I had 32 years of togetherness. A friend recently remarked in total innocence that this must be easier this year. Hell no! This holiday season is harder than the last, when looking back I was in shock and going on autopilot.
    I’ve not done the online dating, but since Diane died I’ve dated 2 women. One who ended up seeing me as a bank account and another who decided that if we continued to see each other it require a commitment and that’s not where she is in life. Although that apparently that did not deter her from entering into a relationship with a friend of mine immediately afterward. The end of each relationship sent me back into the depths of loss and grieving, although I recognize much of the grieving is over Diane’s death and the loss of our life. It also leaves me physically, emotionally and spiritually exhausted. I’m not sure how you all continue forward through this. I never imagined I would be in my 60’s and be in this place.

    But I’m hoping my emotional self can catch up with my intellectual self and come to the point where I recognize if I am going to be in a relationship it’s because I want to be and not because I feel I need to be in order to have a place in life and survive. It’s a work in progress.

    Guess with the new year it’s time to take the plunge into the online dating world. Again, I am happy to see you’re finding peace and happiness. May we all find that in whatever form we need. Wishing everyone a joyous holiday season and a wonderful new year.

    • Debbie says:

      Dear Gary,
      Two years after this kind of loss is so recent. Just to be functioning is the best we can do. It was for me. It was three years before I could even get an inkling that life might be worth living.

      I’m sorry the women you’ve met have been unworthy.But I do believe there are good people out there. What helped me was to look for friends, for me in yoga and hiking groups. And from there I found decent people if not love. Take care.

      • Pam says:

        Your blog has been so helpful. I’ve been involved in our local “young” widows group and that has helped. I’m at three years in three days (right after Christmas, unexpectedly) — and I find I maybe just ready to date. I struggle with looking back at what I had and seemingly, wonder what can be out there. Your comment is helpful. I feel like at three years I should be ready, and I’m much better than the first two years, but still I struggle. It’s good to hear others with the same struggle. I even want to limit my dating to pianists (haha) (J. was one). I’m also an attorney (environmental).

        • Debbie says:

          Thank you so much for writing me. I know what you mean. My husband was a software engineer and I wanted to date someone like him. Someone who had the same qualities.

          And I agree it was so hard not to compare what I had with my husband when I met new people. Most of whom Just fell far short, as people. My husband was a great person, but I did eventually find someone.

          I think people expect us widows to move on and date, but we get to decide when or if we’re ready. We can choose to be on our own. There’s no right answer. It’s what feels right at the time. Take care. I know from experience anniversaries are so hard.

  • Marty Becker says:

    Hi Debbie, thank you again for another informative post. I enjoyed meeting you when I first moved to California in 2014. I am continuing to persevere by contacting women on a couple of websites. Since I live in Monterey, I continue to drive all over the place from as far north as Petaluma & south to Santa Barbara. I don’t mind the expense, because I know the odds are in my favor. As a widower after a 42 year marriage I have much to offer. I know what it takes to have a successful marriage. Thank you again for your posts. Marty

    • Debbie says:

      I enjoyed meeting you too, Marty. I do think that with your persistence and positivity you will meet the right person. It’s just a matter of time. Wishing you a wonderful 2018.

  • Betsy says:

    Debbie, nailed it again. Like I said with the other post, I kept them in my inbox until tonight. It’s Merry Christmas night, and due to the daughter’s different schedules, we don’t get to celebrate until New Year’s Day, a week away. So today I was alone. I was sad, but I was ok also. I have grown much. I enjoy reading your blogs or posts very much. I can relate to so much of what you say. I do believe there are nice older men out there as well. I am 65 now, but due to Bob’s health issues, our intimacy stopped in my 40s, way too young. At first I just want sex, which I never did get, by the way, but now I want companionship, a friend who I can be with, talk with, share with. I am glad you found someone. Also congrats on being in the 50 top blogs. I did say Merry Christmas, but did not realize you were Jewish, so Happy Hannaka. Thank you again. There was a reason for me reading these posts tonight. Love and take care. Betsy

    • Debbie says:

      Dear Betsy,

      Thank you so much. I hope you do find your person.You are so lovely and nice, he will be lucky. I’m good with Merry Christmas or Happy Chanukah.Take care,love, Debbie

  • Jacqueline says:

    Hey, Debbie!
    I’m back from holiday with time to write to you. I am so very happy, not just happy for you, but happy in myself to know your news. Hope that makes sense!
    I am not at all surprised that your blog has been listed in the top 50 for widowed people. I started reading three but only yours seemed worth following. I won’t knock the others but have to say yours is the most real, so honest, sometimes funny, always relatable, it’s the least self-pitying, least self-aggrandizing, and you are so generous in your replies to the comments your writing elicits. I am quite jealous of Marty for having met you!
    I hope this new man realises how very lucky he is!
    Jacqui. xxx

  • Holly says:

    Debbie, this is such fabulous news. I’m happy for you, and I love the space you’ve opened up in you house as well. Possibilities! In addition to perseverance, I would add awareness to the list of what helps in finding a new person after a loss. I was widowed exactly one year, when I met a new neighbor on my morning running route. He was retrieving his newspaper (which we now call “the fateful newspaper”) and we chatted at length. Before too long the occasional morning driveway chat turned into numbers exchanged, a couple of hikes and then six months later we were dating full throttle. He’s so different from my late husband that I wasn’t sure at first whether he was a viable option or not, but I was attracted so I thought I’d give it a go. Glad I did.

    I detail my story for any readers who are still seeking someone out there. Don’t forget to check your back yard. Or front balcony, or driveway down the street. Anyway, that’s my story now. A Happy End to 2017 to both of us Debbie, and Happy New Year to all.

    • Debbie says:

      Thank you so much for sharing your story Holly. I think it will be encouraging to others as well. I agree that awareness is important. Someone could be close by. And openness is important too, You were open to dating someone different than your late husband.

      I’m dealing with when my guy is just different than my husband would be. But that’s okay. Happy New Year to you too!

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