The Dirty Dozen: 12 Men You’ll Meet Dating in Your 40s

If you’ve shopped around for a potential partner in midlife, there’s a good chance you’ve crossed paths with one of these dudes.

When I started dating again after my divorce, it was more fun for my married friends than it was for me. “Ooohh, can I swipe on your Tinder?” they’d ask at the playground, at book club, at church, over coffee, and out for drinks. I’d hand over my phone and let them pass it around, eager to tell me which profiles showed promise and which may as well have been waving red flags.

“What about this one? This one is cute!” (Some of my friends have an extremely generous definition of “cute.”) 

“What does GGG mean?” (Look it up yourself, I’m too exhausted to explain.)

“What is a ‘unicorn’?” (This is when I’d take my phone back and put it away.)

All of my divorced comrades have similar stories; our coupled-up pals love to live vicariously through us as we venture back out into the romantic wilderness, searching for someone to eat dinner with, have orgasms with, maybe even build a life with. But whether we’re looking for some no-strings sex or hoping for a fairy-tale ending—by which I mean, falling in love with someone who is also in love with you, who is available for and capable of a partnership that fosters mutual growth and enriches both of your lives—most of us have found dating in our 40s to be a zero-sum game.

In the 12 years since I gave up on my marriage, I’ve swiped my way through Bumble, OkCupid, Hinge, Tinder, Her, Feeld, and Raya. I haven’t relied solely on the apps, either: I’ve met people at parties, been set up by friends, and gone home with strangers from bars. I’ve dated men ranging in age from 25 to 60 (and a few women, too). I’ve gone out with men of different religions and no religion, men with PhDs and men who didn’t graduate high school. White, Black, Indian, Asian, Latino—I have given them all the old college try. And while I’ve struck out time and time again, I’ve been in the game long enough to give a fairly comprehensive overview of some of the players.

If you’re also out there trying to date in your 40s (or beyond, I suppose—I’m only 48, I can’t speak to the probable horrors of the next decades), you’ll recognize some of the men below.* But if you, like so many of my married friends, are simply curious who’s out there, maybe feeling a little bored or restless, maybe tired of pouring money into couples therapy, or just sick of listening to your partner snort himself awake 37 times a night because he refuses to get treated for sleep apnea, read this before you weigh anchor. I’m not saying don’t get divorced (I’m very pro-divorce), I’m just saying, know the waters you’re sailing into. 

* Note that these men may, and often do, overlap into more than one category. 

The Ethical Non-Monogamist

ENM guy is first, because he’s everywhere. (If you’re going to date on the apps, you’ve got to learn the acronyms.) These are the guys in open marriages, the polyamorists, and the cheaters who used to go on Ashley Madison. Now they can just say they’re ethically non-monogamous, because we’re all supposed to be cool with that these days. I tried to date one once, in the spirit of open-mindedness, but in the course of our initial messaging, we discovered that we had kids of similar ages in the same school district, and I had a friend who worked in his office (though he didn’t know her). “I think our worlds are a little too closely intertwined and it’s best if we don’t meet up,” he said before he unmatched me, making me wonder just how “ethical” that non-monogamy agreement with his wife was.

The last time someone slid into my DMs explaining that he’s in an open marriage and asking if I’d like to get dinner sometime, I told him I couldn’t do it because I want someone to love me the most and want to have sex with only me, forever. And here I am, loving myself the most and having sex with only myself, maybe forever. It’s not so bad!

The Almost-Divorced Guy

Let me save you some time and just tell you: This man is not almost divorced. This man is an optimist, perhaps, or maybe he’s just in deep, deep denial. On the first date, he’ll tell you that he and his ex are using a mediator (he always calls her “my ex,” as if she doesn’t have an actual name) and it’s all very amicable, almost done, papers practically signed.

A few years from now, he’ll be a shell of the man he once was, taken to the cleaners by the divorce lawyer his “ex” found on the Park Slope Parents message boards—the one all the moms said was the shark to call if you truly want to destroy your spouse. But hey, at least he’ll finally be divorced!

The Miniature

I once went on a blind date with a man who showed up early and was already seated at the bar when I arrived. He didn’t get up, and I didn’t think anything of it until we’d each had a couple of drinks, made out a little bit, and decided to continue the date at a nearby karaoke spot. Imagine my surprise when he hopped off his barstool and was nearly a full head shorter than me. Baited and switched! He was cute, so I forgave him. Three dates later he told me I was too old for him. (For the record, he was older than me.)

Another time, I was chatting online with a very handsome actor who my daughter said was “giving short king vibes.” I don’t know how she knew, but she was right. When we met for drinks, my first thought was, I want to put him in my pocket. He told me he went on lots of first dates, but rarely got a second one. (Oh, baby. Sweet baby.) I said yes to a second date because I felt bad for him, then a third and fourth because I genuinely liked him. Then he dumped me and I was righteously indignant about it for months (until I met the next clown in this endless parade). The moral of the story? They’re small, but they bite. Watch out!

The World’s Best Dad

Listen, I have kids. I get it. They’re the center of my world—or at least, they were before they grew up and left me reeling in my empty nest. That’s the thing about kids: they go off and live their own lives, and if you haven’t been living your own in the meantime, you’re going to be lost. That’s what I want to say to the men who put their children in their profile pictures on the apps or who call themselves a “proud girl dad” in their bios.

When I was a child of divorced parents, in the 80s, adults did as they pleased and kids were expected to tag along and deal with it. They told us we were resilient. They said things like, “Grown-ups are talking. Go play.” Now, the tables have turned and kids call the shots. Is there no happy medium? I once dated a man who quickly shuffled me out the door the morning after we slept together, saying that his co-parent was coming over to pick up their child’s favorite cereal because said child was throwing a tantrum and refusing to eat breakfast. 

“Isn’t it her weekend? And can’t she pick up a box of cereal at the bodega?” I asked sleepily, searching his sheets for my underwear.

“They only sell it at the co-op. She’ll be here any minute, you’ve gotta get out of here,” he answered, handing me my bra.

If you don’t mind being compartmentalized and never being a priority, go right ahead and date this dude. Me? I can’t swipe left fast enough if there’s a kid in a profile pic. 

The Hot Mess

He will be hot. Achingly, heartbreakingly hot. He will be charming, funny, and smart. You won’t be able to win a Scrabble game against him, but you won’t care because he’ll be making you laugh so hard you pee your pants (you’re in your 40s, you’ve given birth, he will understand this and be unfazed). He’ll be able to recite Rumi by heart and also know all the words to 36 Chambers. He’ll be a good cook and an even better dancer. He will probably be a Pisces. He will be so fucking cool. He will also be an absolute nightmare to date. “I’m messy,” he’ll tell you, eyes brimming with tears, but you won’t heed his warning. Aren’t we all? you’ll think. In the immortal words of Whoopi Goldberg, you in danger, girl.

The Straight Man

I met this man at a party, where we talked about poetry, playwriting, and hallucinogenic drugs. He was wearing a fabulous scarf and a large, dangly earring, and appeared to be at least 20 years older than me. That is to say, when he asked if I wanted to have dinner sometime, I took it as a platonic invitation, given that he was clearly gay and also much too old for me. We made a date, but the day before, I started to worry that perhaps I’d misread the situation. I texted the person who’d brought him to the party.

“Your friend is gay, right?”

“It’s my understanding that he identifies as straight,” she answered. Damn.

“Oh no. I just assumed he was gay!” I texted back.

“I think you are not alone in this assumption.”

I went to dinner anyway, because I felt bad, and because I am dumb sometimes, and because I hoped maybe he really did want to be friends with me. Alas, this was not the case. He did not want to be friends, and as it turned out, neither did I. I wanted to never, ever see him again—and I vowed to do a better job trusting my instincts going forward. Lesson learned!

The Accordion Player

No, he’s not a musician. (At least, not necessarily.) Picture an accordion, the way it expands and collapses. Now imagine a man trying to fuck you with his accordion. It’s so big! Its bellows are all puffed up! Let’s do this! And then—oh no, what’s happening? It’s folding up on itself, this isn’t working. Wait, I think it’s getting big again. Nope, there it goes, it’s shrinking. Stop trying to shove it in there, stop asking me to blow you for another minute (I already did it for so long that my TMJ is acting up), and stop with the constant intermissions to jerk yourself hard again.

There are medications for this; why is it happening to so many men in their 40s and 50s? Are they trying to gaslight us into thinking they’re fully erect, or are they gaslighting themselves? It’s sad, it really is. Western medicine has solved this problem! Just swallow your pride along with one of those little blue pills already, my man.

Your Friend’s Son

I’m not trying to scare you, I’m just trying to prepare you. If you have a wide circle of friends, some of them a fair bit older than you, and you decide to open up your desired age range and date a little (or a lot) younger—maybe you can’t handle another accordion player and just want to get railed by someone whose energy isn’t going to flag halfway through—it could happen. Does he recognize me? you’ll think. I met him when he came to church with his mom! How is he in my queue? He sent me a rose?! He must not recognize me. I mean, he’s actually pretty cute… could I? Should I? (Reader, I didn’t. But I thought about it. And no, I didn’t tell his mom.)

The Solo Artist

Not all of my dates are bad, in case that’s what you’re thinking. Some of them are fun, with perfectly nice guys who are sweet, quirky, good-looking, quick-witted, and interesting. I had three great dates with one such man not long ago, after which he dropped off the face of the earth with no explanation. I’d met him IRL, not online, and he was vouched for by a friend who knew him well, so I knew I hadn’t been catfished. I was mystified. Months later, he called to apologize for disappearing, explaining that he is “on a solo mission” and “just not a relationship guy.” Let me say again—we’d had three dates. Three. I didn’t think we were headed toward getting engaged, which is what I said to him. We both laughed, and said maybe we’d hang out again one day. Will we? Probably not!

The Meal Ticket

Let’s be real. Sometimes you just want someone to take you to The Capital Grille and encourage you to order the most expensive thing on the menu, plus apps, dessert, and cocktails, knowing there are no strings attached. You can fuck him if you want to, but you don’t have to. He’ll still be happy to buy you another fancy dinner when your bank balance is negative and you need a reason to dress up and be treated like a lady. As a friend pointed out when I balked at paying for a Raya subscription (no free level for the app where you may match with a sad Ben Affleck!), you can easily make back your investment in free dinners. Men make more money than us for doing the same jobs; I’m not feeling guilty about letting them pick up the check every time.

The Prom King

I met this one at a neighbor’s barbecue, but you’ll start seeing him everywhere once you know what to look for. There’s a certain swagger to him, an air of “Get in line, ladies, there’s enough to go around” that’s left over from his high school days. Look closer and you’ll see that his rakish good looks are fading fast; he’s getting paunchy and soft around the edges. He’s been divorced several times and has multiple kids by multiple women. But he’s a good time! Quick with a joke, winks at people, calls them “champ.” Your married mom friends will go wild with jealousy; they’ve been harboring crushes on him for years. You won’t have the heart to tell them he let you pay the tab on every date and he couldn’t get it up. (Parting gift for this dude: an accordion?)

The Perv

Before you leap to any conclusions, hear me out: This guy can be the best of the bunch. I met mine on Feeld, the app for swingers and kinksters, where he went by the handle “Nipple Lover.” True to his name, the man is a true nipple aficionado. An expert in his field. Our relationship has lasted longer than any other since my divorce, and its boundaries are clearly defined. When I need a little ego boost, I text him pictures of my boobs, and he texts back with unbridled enthusiasm, gleeful appreciation, and heaps of praise—no typos, ever. “They have so many different personalities, which is something I really enjoy about them,” he said to me recently. “Your nipples are works of art.”

Sometimes we get together and he goes to town on my nipples; he’s the only person I’ve ever met who knows exactly how to handle them. We don’t kiss. He doesn’t take off his clothes or grind up against me. He’s the least creepy guy I’ve ever known. He just loves nipples! We chat about our jobs, families, politics, whatever’s on our minds lately. He reads my stories and loves my work! He says he has a partner who’s cool with his fetish. Is this true? Who knows, and who cares? Our association is strictly professional. Everyone wins!

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