Join Diane's WomanPause community and receive her free newsletter, amplifying the voices of women over 50 rediscovering ourselves.

Dating Over 50

I have to be honest. I am thrilled to be out of the dating game! (And did I mention happily married?)


I will be turning 60 at the end of the year, but I still clearly remember just 10 short years ago when I decided to throw my hat into the dating ring–and join Match.com, eharmony, JDate, and OurTime …


Whether you’re divorced, widowed, or have never tied the knot, if you find yourself single—or single again—and decide to start dating after 50, you are in for an adventure–not to mention a few challenges. And if you have a sense of humor—God hope you do!—more than a few laughs.


There’s the online dating profile—if you decide to go the tech route. How to find the words to capture your wonderful essence? How to find that right balance, to give enough information—but not too much!



And … don’t forget the pictures. Do you go for the natural look, the so-called candid shots, or do you choose the posed headshot? How about a pic with your dog? (Love me, love my dog/dogs, I’d always say.)


And then there’s the actual meeting—Where? When? Do you email back and forth first, test your compatibility out on the phone, or just jump right in and meet up for cup of coffee?


Who Else Is In the “Picture”?


Does he have kids? How many? How old? Do they live close to home?

What about yours? How are they reacting to Mom stepping out on the town?

So many questions … Don’t forget to breathe!


Here’s yet another one—grim but necessary—and a question that’s often overlooked. Are his parents still alive? If they are (which would be a good thing), are there plans in place in the event they’ll need care in the future? Where are his siblings (if he has any), and have they discussed how they would deal with their parents’ future needs?


Take it from me … one who’s new 90-year-old mother-in-law moved in with us into our small two-bedroom house ONE week after our honeymoon! Love that lady … just hadn’t bargained for an additional housemate! (Did I say ONE week after our honeymoon?!?)  These are important conversations to have BEFORE things get too serious. … Enough said—until I write a blog about it!


And then there’s the first date goodbye. Will there be a goodbye kiss? (I know, so high school!) And what about the real first kiss? Then, the second. And then …


I waited eight years after my first husband died before I started dating again. I was certain I wanted to get back in the saddle but wasn’t convinced I still knew how to ride the horse!


How Friends Can Be Supportive


What about married friends or those currently in a relationship … what can they do to support their single friends who’ve entered the dating arena? I read a helpful article on this very topic in Bustle recently, and I’ll share a few of my take-aways.

First—Show an interest in your friends’ dating experiences. Ask them how it’s going! But … stay clear of giving advice, unless they specifically ask you for it! Sometimes, your friends may just need to vent … and someone who will listen.

Second—A little encouragement goes a long way! Relationship expert Dr. Marisa Franco, told this to Bustle: “Instead of advice, offer empathy and emphasize their worth.” Who among us wouldn’t benefit from a little validation of our self-worth from time to time!

Third—(and this one is directly from my own experience)—whether your single friend is on the look-out for a relationship or is in a good place in the single space, include her in your couples’ outings! My couples friends always invited me to join them and I never felt uncomfortable as a third or fifth or even ninth wheel. Thank you, dear friends—you know who you are!



I Dare You to Read This and Not Smile!


For women everywhere who are dating again, thinking about dating again, remembering their dating years, or just feeling another’s pain, I wrote a piece about the “game” that I’m honored to say was published last month in The VIDA review—a wonderful journal (so please take a look at the last issue and enjoy!)


With all the tumult going on around us all these days (whether we’re single, dating, or married), I thought I’d share my little piece below.


I dare you to read it and not smile!!


Virtual hugs to all, and remember, it’s never too late to find love!


As always, I’d love to hear your thoughts—about dating or anything else. Please leave a comment or send me an email!

See you October 19th







I’m walking into La Strada, a little Italian joint in Merrick, Long Island, on a Wednesday evening, when I see this guy who I think is Steven, slim, gray, and about 5’10, standing beside the bar on his cell phone. I hear him speaking to someone about contracts and inspections. I’m guessing he’s buying a house, or selling one, which is a good thing, because currently, he’s living with his ex. (I know this because he told me on the phone after we emailed and exchanged numbers, after we saw each other’s profiles on Match.com, and after one of us made the first move—that was me.) She’s not officially his ex, by the way. Not yet, anyway, but soon. Soon.


He’s attractive, more attractive than his pictures, and so far, he seems nice. But, then again, so am I, and I just want to get this show on the road because this first-date ritual is just an initial job interview, after all. To make it past that all-important first round, you need to keep it short and keep your baggage close. Being with me, for example, and my nineteen-year-old son who’s still living at home would be like working overtime for half the pay. Not sure Steven would be up for the gig, so I’m definitely not going to share all that tonight. Not on the first date. Maybe next week. Maybe.


Could It Be a Sign?


He finally ends the call. We make eye contact—he’s got lovely luscious brown eyes—and shake hands. He apologizes for the delay, I make note of his good manners, and then we sit at a cozy table against the left wall of the dining room and order red wine with our pasta. My dish has eggplant and red sauce—I’m a vegetarian —and his has chicken. Meeting for dinner like this is unusual. Could it be a sign?


I rarely do dinner on first dates, but when Steven mentioned he had a Groupon, I thought, what the heck. Coffee is safer, always much safer, because Starbucks offers a quick escape. Not that I fear bodily harm—I always arrive and leave in my own car—I just hate wasting time, stuck in a going-nowhere conversation with a man with whom there is no click. But I feel a click here tonight, not a love at first sight thing, more like an “I’ll give it another go.” I’m kind of liking Steven’s gentle vibe and his smile.


He talks about his three kids—two of whom he says are “profoundly” deaf. Just as I’m wondering what exactly that means, he starts to tell me about the youngest. That one acts and sings in plays—high school plays. Steven tells me that he never misses a performance, which is sweet, I guess, but I’m already thinking of all the times I begged my own kids not to join school band because I couldn’t bear to go and sit in the school auditorium on those hard wooden chairs for the spring and Christmas concerts to hear a bunch of elementary school kids play the trumpet or the sax off key. I mean, wasn’t chorus enough?


Make Me Laugh and You’ll Win My Heart


So, I’m not Mother of the Year, but Steven’s not looking for a mother, and I’m not in the market for a son. We decide to meet again, on Saturday this time, the coming Saturday, at Governor’s in Levittown, a local comedy club. The guy likes to laugh. So do I. (I put that in my Match profile, by the way, something ridiculous like “make me laugh and you’ll win my heart.” I know it’s incredibly corny but it’s true—and it’s been such a long time since I’ve had a good laugh.)


I’ve never had to play the dating game before. My first husband—who was very funny by the way—was also my childhood sweetheart. We had been together since I was fifteen, that is, until eight years ago. It was eight years ago, in November, that my first husband was in a car accident. He died. You know, life really can change in an instant. Ours did. Bang. Boom. Gone. But now, and I’m not quite sure why it’s taken me this long, now, after eight years of sharing my bed with my dogs, I’ve decided it’s time for me to rejoin the living. I’ve decided it’s time to join Match.com.


Fifty, Female on Match


Being a fifty-year-old woman on Match, I quickly learned, is a lot like looking to buy prime real estate in a great school district on a limited budget. You just might have to settle for a foreclosure. Most men my age or older (or even much older) tend to limit their search parameters to the magic number “49.” A man, let’s face it, may be in his 60s and still see himself as a major catch for a hot younger woman—his daughter’s age, for example—while the woman, the hot, young woman, he convinces himself, will still love him for his mind. Online dating really is like searching for the perfect home. You start out with big hopes and bigger dreams but quickly land right back down on earth—with a thud. There are always concessions: would you rather have the extra half bath off the first-floor hallway or the bay window in the living room facing the street? I know it’s tough, but you must make a decision. Darling, when you’re over 50, you simply can’t have them both.


Would I choose the man who studies numerology and swears that the numbers in our names—I always thought they were letters—made us the perfect match? Or the man who is great fun, who had been married to a woman who had two kids from a previous marriage, kids he put through college? That guy is very generous. So generous, in fact, he had also paid for an apartment in Manhattan for a woman he was seeing on the side. She was young (I rest my case) and couldn’t afford an apartment on her own. I guess you could say the guy’s generous to a fault. Maybe more than one fault, come to think of it.


We ALL Make Mistakes


Now, don’t get me wrong. I’ve made some blunders in this dating game, too. There was one man I really wanted to meet. We had spoken on the phone a few times. He sounded so handsome—I think it was the music in his voice. He was quirky, genuine, and kind. But I called him one night after having dinner with a friend, where I guess I had one, or one too many, before the main dish came. So, I told this man whom I wanted to meet, this man I really wanted to meet, told him exactly what was in my heart: “I just want someone to rescue me.” Yes. I actually said that—and that was the last time we spoke.


“I just want someone to rescue me.” Isn’t that the real American dream? Someone who sees you in distress and wants you anyway. Someone who can look beyond the very messes you’ve made and is not afraid. He doesn’t have to be tall, or dark, or especially good-looking. He just has to want me, love me, and lift me out of my life.


I will learn soon, as I suspect even now, that fairy tales do not come true. I will learn that it is I who must be my own knight—strong and gentle with myself. I must accept who I am and the bed that I’ve made. And learn I can always change the sheets.


“Thank You” for Today and “Please for Tomorrow”


I will see Steven again on Saturday, this Saturday, and we will laugh at the local comedians on the Long Island stage and smile at our good fortune. We will think that we’re on to something here.

Two years later, we will marry in a ceremony on the beach, with dear friends and family all coming together to wish us the best. I will have gotten to know his kids—I will even go to one of his youngest’s high school plays—and he will have gotten to know mine. (He and my nineteen-year old will have become great friends.) And I will have learned to breathe. And he will have learned to trust. And we will create a new life together, in a teeny, tiny house by the Long Island Railroad. And that house will vibrate whenever a train passes by. But we will have built a sturdy enough foundation to withstand a few shakes. And we will laugh, at the world, at ourselves, at the crazy way we met—we still won’t have gotten used to the concept of clicking for love—and we will say “thank you” for today and “please” for tomorrow. And that’s the happily-ever-after that will be mine. And it is better than any fairy tale I ever thought I wished for. Because this is not a dream, American or otherwise. It is real—I can touch it—and when I wake up, it will still be there.











  1. Linda Marie Bicksler on October 9, 2020 at 2:12 am

    I adore your writing. You’re a true professional.
    Where do I know your name from?

    • Diane Gottlieb on October 9, 2020 at 7:44 pm

      Thanks so much Linda! I appreciate it!
      I’m not sure where you’ve heard my name? Any ideas?

  2. Denise Polis on October 6, 2020 at 11:04 pm

    Beautiful story. So happy for you!
    I remember that dating in my 30’s was a nightmare!
    I can’t even imagine how much more difficult it is in your 50’s and above!

    • Diane Gottlieb on October 7, 2020 at 1:59 am

      Thanks Denise!
      I think dating at any age has it’s own challenges. When you date over 50, a sense of humor goes a long way!!

  3. Sarita K Sid on October 6, 2020 at 8:52 pm

    Loved your work in Vida when I read it recently & appreciate this blog post too. I didn’t know your 90-year-old mother-in-law had moved in with you a week after your honeymoon, but that shouldn’t have been a surprise wedding gift for you, my dear 😉
    My older daughter met her husband on a dating site and my older sister is now seeing someone she met online during the pandemic. The spreading of love is a welcome relief from stories about spreading coronavirus 🙂

    • Diane Gottlieb on October 7, 2020 at 1:57 am

      Thanks, Sarita! And yes, what a surprise wedding gift it was!
      Love this: “The spreading of love is a welcome relief from stories about spreading coronavirus.”
      So true!!

  4. Jennifer on October 6, 2020 at 2:48 am

    Love this!!!! ♥️♥️

    • Diane Gottlieb on October 6, 2020 at 3:01 am

      Thank you Jen!! XOXO

  5. Sherry Danner on October 5, 2020 at 2:55 pm

    So glad you shared this here. I read your article in The VIDA review and loved it! We need more honest (and hopeful) later-life love stories like yours out in the world. The last paragraph is a work of art. Any woman who has sought the “fairy tale” and stumbled upon the real thing instead will feel it in her bones.

    • Diane Gottlieb on October 5, 2020 at 3:05 pm

      Thank you so much, Sherry! And your last sentence is a work or art: “Any woman who has sought the ‘fairy tale’ and stumbled upon the real thing instead will feel it in her bones.” Made me cry!

  6. Shari Gaudet on October 5, 2020 at 2:29 pm

    This is wonderful and the second time I’ve read it. Now have to send it to my recently divorced friend who is dreading the dating game. Thank you!

    • Diane Gottlieb on October 5, 2020 at 2:50 pm

      Thank you, Shari!! I hope it gives your friend some hope!!

  7. Sue on October 5, 2020 at 1:41 pm

    What a beautiful story💛

    • Diane Gottlieb on October 5, 2020 at 2:49 pm

      Thank you Sue! Great to hear from you!!

  8. Linda Rochester on October 5, 2020 at 12:40 pm

    Wonderfully written story! My son met his wife on a dating site. I think highly of the dating sites. That way you know a little something about the person. It’s a time saver. Course we all love a love story. This is a very nice thing to read in the morning. I hadn’t thought about online dating during the covid crisis. I’ll bet that has crashed like everything else.

    • Diane Gottlieb on October 5, 2020 at 2:49 pm

      Thank you, Linda! My daughter met her husband on one too! I’ve heard the dating sites are still going strong–even with COVID! How we will adapt for love!

  9. Alison on October 5, 2020 at 12:18 pm

    Aww! YAY YOU! What a beautiful, real story. Makes me smile. XO

    • Diane Gottlieb on October 5, 2020 at 12:20 pm

      Thank you, Alison!! I think we can all use some happy stories these days!

Leave a Comment