Casual Dating After 40: A Straight-Talk Guide for Men

I got divorced at 43. The last time I'd been single, people still printed out MapQuest directions. What followed was a couple of years of being rusty, embarrassed, occasionally very lucky and frequently confused. This is the guide I wish someone had handed me: casual dating over 40, written by a guy who did it badly before he did it reasonably well, covering custody schedules, old photos, the health talk, and how to say you don't want a relationship without being a jerk about it.

The first six months after the divorce are weird. Let them be weird.

Nobody warned me how strange it would feel. One week I was a husband with a mortgage and a minivan and an opinion about lawn fertilizer. A few months later I was sitting in a two-bedroom rental with a futon and a kid's bunk bed I'd assembled wrong, trying to figure out whether I was allowed to want sex with a stranger.

You are allowed. That's my first piece of advice. But I'd also say, give yourself a minute before you start. I jumped in about three months after I moved out and I was a mess. I talked about my ex on the first two dates I went on. One woman, very kindly, at the end of a drink, said, "You're not ready, are you?" and she was right.

I don't think there's a correct waiting period. Some guys are fine right away because the marriage was over long before the paperwork. Some need a year. You'll know you're ready for casual dating when you can go on a date and not mention her once. That's the test I use now, and I've passed it and failed it more than once.

You're rusty. Everyone is. Here's what changed.

If you were married for fifteen or twenty years, the whole way people meet has turned over at least twice. When I was last single, you met women at bars, through friends, at work (not recommended), and if you were adventurous, through the personals in the back of the weekly paper or on Craigslist.

Craigslist personals were gone by the time I got back out there. They shut down the whole US section on March 22, 2018, the day after the Senate passed FOSTA-SESTA, and they never came back. I'd used them in my twenties and it was kind of a shock to find out. If you missed that whole saga, I wrote up what happened to Craigslist personals in another piece.

What replaced them was mostly swipe apps, and swipe apps are, to put it gently, not designed for us. They're built for people who have time to swipe for an hour a night and message twenty matches. They reward young, photogenic, and fast. A 46-year-old with a decent job and two kids and a very specific Tuesday night free gets buried.

There's still a world of personals-style sites and directories where text matters, where people say what they want up front, and where nobody's pretending a casual thing is a romance. I compared a lot of them in my Craigslist personals alternatives roundup, and I also wrote about apps versus sites if you're trying to figure out which kind suits you. I'll admit I'm biased toward the personals format. It suits men who are better at being decent in writing than at being hot in a thumbnail, which describes most of us over 40.

Your photos are from 2011. Fix that first.

I say this with love. Every divorced guy I know has a profile photo from a wedding about a decade ago, cropped so you can see a sliver of his ex-wife's shoulder. Or a photo with a fish. Or a photo where he's thirty pounds lighter and has hair.

It doesn't work, and it's worse than not working. If a woman meets you and you look visibly older or heavier than your picture, she spends the first twenty minutes of the date recalculating, and she's annoyed. You've started by lying, even if you didn't mean to.

Get a friend to take three or four photos of you, this month, outside in daylight. One smiling, one doing something you actually do, one that's just your face clearly. That's it. You don't need a photographer. My brother-in-law took mine on his phone in a park and they were the best photos I'd had in years, mostly because I was laughing at him.

Gray hair is fine. Reading glasses are fine. A few extra pounds is fine. Women in their 40s and 50s are not expecting a 28-year-old, and a lot of them are relieved when they see a guy who looks his age and seems comfortable with it.

What women in their 40s and 50s say they actually want

I can't speak for all women, obviously, and I'd be suspicious of any guy who claims he can. But I've had a lot of honest conversations over the last few years, some with women I was seeing and some with women I'd just become friends with, and certain things came up over and over.

A lot of them have done the marriage thing. Many have kids, some grown, some still at home. They have careers. They have a house set up the way they like it. And a surprising number of them, more than I'd have guessed, have no interest at all in getting married again or moving a man into their space. One woman I saw for most of a year told me, "I raised two kids and one husband. I'm not doing laundry for anyone else." She wanted a guy she could see on Saturdays and who went home on Sunday.

That's a pretty good fit for a lot of us.

What they've said they don't want: men who are secretly looking for a new wife and pretending to be casual. Men who want a nurse. Men who complain about their ex for an hour. Men who are pushy about sex, or weirdly passive about it, or who disappear for two weeks and then text "hey stranger." And men who lie about being married.

What they've said they do want: someone who's honest about what this is, shows up when he says he will, is clean and takes care of himself, is decent company, and is a considerate partner in bed. That's not an impossible list. It's mostly just being an adult.

On personals boards you'll also see women seeking older men specifically, sometimes women in their thirties who've had enough of guys their own age. I've met a couple. It's real, but I'd say don't build your whole plan around it. The most reliable fit, in my experience, has been women within about ten years of my own age either way.

The custody calendar runs your love life now

This was the biggest practical adjustment for me. When the kids are with me, I'm Dad, full stop. Pickups, dinner, homework, the eternal search for a matching shin guard. I'm not going on dates and I'm not inviting anyone over. When they're at their mom's, I'm suddenly a single guy with a lot of empty evenings.

What I figured out eventually is that this isn't a weakness. For casual dating, it's actually kind of perfect. A woman who's also on a custody schedule, or just busy, often loves a guy who says, "I'm free every other weekend and most Wednesdays." It's predictable. Nobody has to wonder if this is turning into a relationship, because the calendar keeps it in a box.

Say it up front. I put it right in my profile, and it turned out to be one of the things women responded to most. It reads as honest, it reads as a responsible father, and it quietly tells her this is casual without you having to make a speech about it.

A couple of rules I set for myself. Nobody I'm casually seeing meets my kids. Ever. Nobody stays over on a night before the kids come back, because the house has to look normal and I need to not be tired. And I don't do dates on my kid weeks, even when it would be convenient, because the one time I tried it I spent the whole night checking my phone for the babysitter.

Your kids will find your phone

They will. Mine did. My daughter was eleven and she was looking up a video on my phone and a message notification popped up. It was nothing explicit, thank God, just a woman saying she'd had a nice time. But I had about five very uncomfortable minutes of conversation I wasn't ready for.

Turn off message previews on your lock screen. Put the apps you use in a folder that isn't your home screen. Use a passcode your kids don't know (and if they've been watching you type it for years, they know it, change it). If you're using a site in a browser, use a private window or log out. And be thoughtful about email notifications, because a lot of sites send them and a lot of kids read the family iPad.

Discretion matters for other reasons too. You might have an ex who'd love some ammunition in a custody dispute. You might work somewhere conservative. You might just be a private person. Most women in our age bracket feel exactly the same way, which helps. Plenty of them are dealing with the same thing on their end.

This is one reason I lean away from apps that link to your social media and toward places that don't. If privacy is high on your list, I go into some of this in my guide to staying safe meeting women online.

How to say you're not looking for a relationship (without sounding like a jerk)

This is the part guys get most wrong, and I got it wrong for a while too. Either they hide it, and pretend to be open to a relationship to get dates, which is dishonest and blows up later. Or they say it like a disclaimer on a contract: "Just so you know, I'm NOT looking for anything serious." That second one is technically honest but it sounds like you're bracing for her to fall in love with you, which is a little arrogant.

What's worked for me is just saying it as a fact about where my life is, not a rule about her. Something like: "I'm about two years out of a long marriage and I'm not looking to get into anything serious right now. I'd really like to meet someone I enjoy spending time with, and if that's casual for both of us, that sounds great." Then I stop talking about it.

Say it early. In your profile or ad, and again before you meet. Don't wait until after you've slept together. That's the worst time to bring it up, and it'll feel like a bait-and-switch even if you never promised anything.

I also think it's fair to check in now and then if something goes on for months. Feelings change, sometimes on her side, sometimes on yours. A quick "is this still working for you?" every so often is not a big deal and it avoids a lot of hurt. The friends with benefits guide goes into the ongoing kind of arrangement in more detail.

If you're writing a profile or an ad from scratch, I put a few real examples in my guide on how to write a personal ad, including one from a friend who was 47 and wanted exactly this.

The health talk

I'm going to be frank here because nobody else will be.

If you were married for twenty years, you might never have had a conversation about STI testing with a sexual partner. I hadn't. I didn't even know what a standard panel included. And when I got back out there, I found that women in their 40s and 50s were often much more on top of this than I was. Several asked me, before we did anything, when I'd last been tested. The first time, I had to say "uh, never, I was married." Not a great answer.

Get tested before you start, and then periodically while you're active. Your regular doctor can do it, or a local clinic, and in a lot of places it's not expensive. Ask what's included, because not every panel covers everything. Then bring it up yourself, before things get physical. "I got tested last month and everything was clear, happy to show you. When were you last tested?" It's a thirty-second conversation, and it makes you look like a grown-up. Every woman I've had it with has been relieved rather than put off.

Use condoms. I know. I know. But the fact that pregnancy might be less of a worry at our age doesn't mean the rest of it goes away, and I'll leave the medical specifics to an actual doctor.

About the equipment

Here's something a lot of guys over 40 worry about privately and never say out loud. Things don't always work the way they did at 25. Nerves make it worse. A new partner makes it worse. A couple of drinks makes it worse. Being out of practice after a sexless last few years of a marriage, which is a lot of us, definitely makes it worse.

It happened to me the first time I was with someone new after the divorce. I was mortified. She was completely unbothered. She said something like, "It's fine, we've got all night," and we did, and the evening was great anyway.

A few honest things I've learned. First, it's common, and most women in our age range have run into it before and don't think it's the end of the world. The way you react to it matters more than the thing itself. If you get embarrassed and sulky, that's what ruins the night. If you laugh and pay attention to her instead, it usually turns out fine.

Second, if it's happening regularly, go talk to your doctor. Seriously. It can be connected to other health stuff worth knowing about, like blood pressure or heart health, and there are treatments. I'm not a doctor and I'm not going to recommend anything specific, but I will say I put that appointment off for months out of embarrassment and the conversation itself took about four minutes.

Third, the best sex I've had in my forties hasn't been the most athletic. It's been with women who knew what they liked and told me, and with whom I wasn't in a hurry. That's one of the real upsides of hookups over 40. Nobody's performing.

Where to actually meet women for casual dating over 40

I've tried most of the options. My honest ranking, which is just my experience and could easily be different in your town:

Swipe apps are workable if you're photogenic and patient, frustrating otherwise. The women there who want casual are often buried under the women who want a relationship, and nobody's quite sure which is which.

Bars and the like are better than people say, if you go to places where people our age actually go. Not the college bar. More on that in my guide to meeting women without dating apps. The downside is you have no idea what anyone's looking for.

Free personals boards and Reddit are hit-and-miss. There are real women on them, but the ratio of men to women is lopsided and the fakes are everywhere. I wrote about what free really costs in my piece on free hookup sites with no credit card, and I'd read it before you hand anyone a card number.

Directories where women list themselves and say what they want are, for me, the most efficient by a lot. You know she's looking. You know roughly for what. On W4M Maps the women have been checked with an ID and a live video call, which at our age, with limited free nights, matters. I don't have hours to burn on a profile that turns out to be a bot in a call center. If you want a walkthrough of how to search by area, I wrote up finding women seeking men near you.

Where you live makes a big difference, and I don't want to pretend otherwise. When I was in Ohio there were plenty of women my age listing, mostly in and around the bigger cities. A friend in rural Montana tells me it's a different world out there, fewer options and longer drives, and discretion matters more because everyone knows everyone. In big sunbelt states like Florida and Arizona, I've noticed a lot of women in their 50s and up listing, which makes sense given who lives there. Worth browsing your own state for twenty minutes just to see who's actually around before you decide anything.

Casual dating for men over 50 is mostly the same, with a few differences

I'm in my late forties now so I can't fully speak to this from experience, but I have friends in their fifties doing it, and what they report lines up.

The pool of women who want casual gets, if anything, bigger. Kids are grown, careers are settled, and lots of women in their fifties have been widowed or divorced and know exactly what they don't want. One buddy of mine, 56, says he's had more honest conversations about sex in the last three years than in his entire marriage.

The health stuff gets more important. Not just testing. Being in decent shape, sleeping enough, knowing your own body. It affects everything.

And the tech can be a barrier. Some men over 50 find the whole online thing exhausting and a little humiliating. If that's you, start with something simple, where you read a woman's listing and send her a normal, respectful message. That's closer to the old newspaper personals than to swiping. I wrote up how to message women online for exactly this, and none of it requires being good with phones.

A few things I'd tell myself at 43

Don't rush. You're not behind. There's no clock.

Be honest about what you want from the first message. It filters out the wrong people and attracts the right ones, which is the whole point.

Don't confuse being lonely with wanting a relationship. They feel similar. They're not. A lot of what I thought was wanting to get remarried was really just wanting to not eat dinner alone four nights a week, and casual dating plus a couple of good friends fixed that.

Pay for the first drink. Show up on time. Text when you say you will. These things are so basic and so rare that they'll put you ahead of most men on any site.

And don't hate yourself for the dates that go badly. I had a first date where I knocked a full glass of red wine onto a woman's white jacket in the first five minutes. She laughed, we had a great night, and we saw each other on and off for a year. Another time I did everything right and she just wasn't into me, which is fine, and happens, and isn't a referendum on your life.

I'm not sure I've figured all this out. Some months go great and some months are dead. But I'm a lot happier now than I was in the last few years of my marriage, and a big part of that is that I stopped feeling like I'd aged out of being wanted. You haven't either. When you're ready, go browse w4m personals in your state and see who's out there. You'll probably be surprised.