The Precarious World of Online Dating After 50

“You’re cute, do you have a younger sister?”

“Hi there, what is your sexual appetite?”

“Can I fist you? Women in their 20s and 30s don’t like to be fisted?”

“How bout a full-body massage in exchange for a shoulder rub?

“No way you’re THAT old”

“I have mommy syndrome and would be heaven going down on you”

That’s just a random, word-for-word sampling of the text messages I get from my online suitors. No kidding — these are their opening salvos. You’d think men would have matured by this time. In fact, the opposite is true.

To be honest, I never would have imagined that I’d be single post-50, without kids and attempting to date in New York City. But, alas, this is my predicament.

Independent, financially secure and very, very single.

And it’s challenging. I often equate quality single men over the age of 45 to the endangered species list updated nationally by the government. Where are they hiding? Certainly not on the dating apps/sites I have tried over the last two-plus years.

OK Cupid, Bumble, Hinge, Happen, Tinder, Match, eHarmony… I’ve tried them all.

Back in 2003, I moved to New York City from Seattle, following a divorce after an 11-year marriage. The last time I had actually dated was 1989 — AKA, pre-internet, pre-social media, pre-cell phones. I had to learn to date (and have sex) all over again.

But online dating from 2003 to 2006 was quite different than it is today. People actually took the time to create profiles and would even READ your profile before trying to contact you. No longer. Today, we live in the era of swiping. When asked what sites are best for women, I laugh — I see the same men on all of them with slightly different takes to their very short descriptions.

It was between 2003 and 2006 that I met the man I would be with for eight years in what I thought was a committed relationship. As things broke down, my fear of going back to the dating world struck a chord of horror in me and kept me stuck in a very toxic and negative situation. As bad as things were, returning to the world of digital dating was a decision I desperately wanted to avoid.

Nevertheless, I ultimately found myself back on the market. So here I am today: swiping, swiping, cringing, laughing and, yes, sometimes crying. And, yes, I force myself to keep it up, as painful as it can be. I also accept dates from men who may not seem ideal on paper because one never knows.

So far, other than a small number of positive connections that led to a few weeks of dates, I can honestly say I’ve been far from “enchanted” by online dating in recent years. To get by, I try to tell myself that one can always benefit from making new friends and acquaintances.

When we finally sat down at another bar, within minutes he started to tell me about his ex-wife’s infidelity. THIS WAS THE FIRST DATE.

Most of the dates have been the epitome of dull. Recently, I was to meet a fellow at June Wine Bar in Cobble Hill. He was coming from Manhattan and did not know his way through the streets of Brooklyn. He expected the bar to be right across from the 2/3 train stop at Clark Street, and instead it was about a mile away. He never even checked the map! He called me completely lost. I took pity on him and wrapped up my tab at the bar to dash off and meet him closer to the stop.

When we finally sat down at another bar, within minutes he started to tell me about his ex-wife’s infidelity. THIS WAS THE FIRST DATE. His words slid into what sounded like the adults in Charlie Brown comics, and I started to daydream about going home and cuddling with Phoebe, my pup. After two glasses of rosé (while I mentally planned my week of client work), I politely said goodnight and exited the establishment.

Another date ended as quickly as it had started when my date broke it to me that he voted for the current white house occupant but was too “chicken” to tell me before-hand.

The good news is that I date on my terms: I select places close to home for an easy escape, I always ask a friend to call me so I can say “an emergency” has come up and I must depart and I definitely choose watering holes that I know will have a decent selections of wines-by-the-glass so I can have some fun. Lastly, during spring or summer, I pick outdoor spots so Phoebe can accompany me. She makes an excellent chaperone and has exceedingly good taste.

As an optimist at heart, I’m convinced that I must keep trying. When asked if I’m looking for the “one,” at this point, I honestly do not know. A friend with benefits who is intellectually curious with a love of travel and adventure has a very nice ring to it. I am, however, looking for that real connection, deep conversation and mind-blowing sexual intimacy.

And two-and-a-half years following my painful break-up, I’m still searching.

(Salacious texts provided by author)

Tell Us in the Comments

What do you think?

20 Responses

  1. Elisa

    Susan, I am right with you and I HAVE tried them all… I’ve actually had some nice ‘meets’ but not guys I wanted to date. I get my share of married men who all have wives who no longer have interest in sex. I hear from a lot in their 20-40s… And I have really given some of them ‘heck’ when they start with the sexual… Jeez! I’m three years in and have no idea what I want… but I am certainly not finding it. I’m grateful for my wonderful friends–male and female–who make my life fun and interesting. Luckily, I am ok with my own company.

  2. Catherine

    This was a good read for me as I went on my first Bumble date at age 52 after being divorced for 11 years and single for the past 7 years. At this point I just want a friend that could turn into something more meaningful. I like being alone – almost too much. The thought of rushing into something or the dreaded LTR reference makes me cringe and want to run.

    My date consisted of dude talking about himself a lot. He was proud to show me he has clips on his gloves like the ones we had as kids. He was 60. He also told me he’d pick up the coffee “this time.” Ugh. Done.

  3. Lesley seymour

    Oh no. This is so horrible. We must find real dates done the old fashioned way. You are way too special for this. xoxo

  4. Jennifer Mayerle

    Oh Susan, I so feel your pain. And not because this is my predicament, but it’s because I’ve spent the past few years walking along with you — literally – seeing you pick up your phone to get a text from a guy who appears so great, as you say, “on paper.” Nice looking, interesting background, active, etc., only to watch the conversation go straight to the gutter and your hope wane. The comments are disgusting and despicable. No human being should talk to another like that. (But that’s just “locker room talk”…don’t get me started….). But you continue to hold your head high and hold out hope, and that, from all you’ve through, is so admirable, and I hope you take pride in that. Great article…great things have and will continue to come your way…and most likely one of those things will be a great partner…or, better yet, a friend with benefits. Ha! Love you, friend!

    • Elisa

      One other thing I will never understand… You start a conversation with someone.. it might even go for a few weeks or even a month or more.. and they nothing… They just flat disappear. Will someone please explain this to me? Did I say something wrong? i will never know…one thing I DO know is that you can not make someone like you or even love you… I have to keep saying to myself–it is their loss!

    • Susan McPherson
      Susan McPherson

      Thank you my dear friend!!

  5. Karen

    OMG Susan!!! Reading these is shocking! I guess I’m not shocked, but I am, but I’m not?! Whoa.

  6. Josh

    Not defending men, but I am one. Normal, I think. There must be good men out there because I’m looking and last time I looked I looked and sounded ok 🙂

    Just saying: don’t scare away the good ones, wherever they are!


  7. Sara Chipps

    The rule is it takes half the time of the relationship to get over your last, so you have a year and a half left which is no time at all :). All kidding aside, this was a great article. It mirrors the stories I hear from my best friend who just turned 40 and has similar interactions that you are describing ( is my favorite). It’s a horrible envronment when there is anonymity involved. There is a big hole in the market right now that someone needs to fill with a series of events or something similar.

    You two should talk.

    • Susan McPherson
      Susan McPherson

      oh Sara!! Crazy, right?! I will check out your friend’s post and so appreciate you taking the time to comment.


  8. sharon

    Sounds oh so painful AND annoying! JERKS! sorry.

  9. Valorie

    I’m 6 yrs in. I gave up on online dating thing last year. If I’m meant to have a meaningful romantic relationship then he will walk into my life. I am so ok with being with my own company and so tired of kissing frogs. I met soooo many creeps online and a few that covered it up well till you met them. I just won’t subject myself to that anymore. I go out with friends and meet people all the time I have not given up on love just finding it on an online dating site. If I lived in NYC I would go to those meet ups or speed dating looks kinda fun at least for a minute. I love myself too much to purposely subject myself to the hassrassment and abuse that I have encountered in on line dating.

  10. Foster C

    I understand the frustration with online dating, it’s the worst! I’m 33 and was on & off every dating app under the sun for a decade while living in NYC. I left NY last year for Dallas & assumed as soon as I got away from there I’d easily meet some marriage ready, fabulous guy.
    Ha, not quite! A year later & I’m still searching – turns out it wasn’t NYC’s fault completely, it was also my unrealistic expectations and poor choices in men.

    I think one of the problems with online dating is that it’s easy to dismiss someone for not blowing you away right off the bat. I did it all the time and would sometimes regret it later. It’s a first date with a complete stranger and not everyone is immediately impressive or smooth. It’s good to have standards but it’s also good to give men a little break. Some of them are simply clueless but they’re good guys underneath.

    We NYC ladies are go getters: we’re strong, curious, talented, adventurous, not afraid to speak our minds and want someone very unique who has those same qualities. But those quality exciting guys are very hard to come by..(at least the faithful ones.) Our standards are super high (which is great!) But maybe we should not write off the seemingly bland or awkward guys so quickly. Take that weirdo under your wing and he might surprise you!

    The guy who came from Manhattan & didn’t know how to navigate BK..I’ve been on a date with a guy just like that. Several times actually. That guy never had to push himself out of his comfort zone. He’s a dude of routine and comfort and needs some guidance. Or maybe he’s new to the city, or he hasn’t made friends with any BK people yet. Instead of thinking “what a loser, he doesn’t know how to get around BK and has no sense of adventure” turn it into an opportunity to show him some cool places and educate him. Some men need to be led to water and once they get a taste they will keep coming back.

    I hope I’m not sounding preachy because I totally empathize with your plight. You sound very strong and brave. Dating is not easy in your teens, 20s, 30s, 40s, 50s or beyond. My 63 yr old mom is recently widowed and her dating life is a disaster! She’s got everything going for her but her options are so limited that the local shut-in is starting to peak her interest. But I know she will find love again someday, just like you will. In the meantime, give someone a chance you might not normally let in your life. Go outside YOUR comfort zone. And enjoy your own life in every way possible whether you have a partner or not. At the end of the day, it’s all that really matters.

    • Susan McPherson
      Susan McPherson

      Thanks so much for commenting and sharing your experiences!! Not sure how strong I am, but I definitely take risks. Life is too damn short!!


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