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Three Guys on Dating After 60

The politics; the etiquette; the apps; the whole dating scene — how do you navigate a world that’s radically changed from what you remember?

If you settled down in your 20s and 30s, then hit the dating scene again in your 60s or beyond, it’s fair to say things will have changed — perhaps unrecognizably. So what’s that like? We asked three guys aged 60+…

Finding Common Ground With Barium and Intestinal Issues

Andrew, 65: I got divorced, and right after that, my father died, so I wasn’t really in the mood for playing games with dating. I didn’t wanna waste all that time dealing with all that crap. So my main thought about dating at that age was that it would just be better to get a hooker. I have all these friends in L.A., lawyer and producer types, and they can afford to live this lifestyle where they have high-priced sex workers who show up, they do what they want, and then the sex worker leaves.

I once tried to go to a bar with a friend of mine who’s married. We went to this local bar that was known for having a big singles scene on Thursday nights. I was frightened at the whole scene, but he got into a long conversation with this woman in sales. He started the conversation by saying, “I really like your watch.” And they had this whole discussion about watches, which… I couldn’t have that discussion. Plus, at a certain age, it’s really hard to hear in a bar. I used to be able to stand in a nightclub with music blaring and I could listen in on a conversation I wasn’t even having. But at this point, if you talk to me in a bar, I’m just gonna shrug. Also, I’m short and not very attractive to most first-impression people. What’s most attractive about me is my gift of gab, which you can’t hear in a loud bar. So that whole scene was out.

I haven’t ever internet dated either. I just couldn’t bring myself to do it. I started with a profile, but well, I’m an artist, and I’m a little more famous than most people. I wasn’t putting my fucking picture on some dating service! I just thought I was more of a public figure, and I wasn’t doing that. So for a while I considered hookers, and even went so far as to call some up. But nobody would call me back! I couldn’t get any callbacks from the hookers either! So then I really felt like a pariah.

Luckily, a friend fixed me up. On our first date, I remember we both recently had barium swallows for our intestinal issues, and we’d discussed that at dinner… that was great. And although she now gives me shit for bringing it up, she’d just had it, and I’d had mine. Anyway, that’s dating as a senior.

Another thing you learn as you get older is that women don’t like to eat before they fuck. That’s the dumbest thing: You’re supposed to take them out, stuff them with food and then they really don’t want to do anything because they feel fat. The other thing about dating as a senior is at some point, you have to learn about lube. Most straight men don’t use it — well, I never did. I relied on natural lube, and I never went to places that weren’t naturally lubricated. But after a certain age you have to learn to be good with the lube — you have to work it into your act.

Even though the world has changed a lot in the past five years, political correctness has never been a problem, and I’ve always been a gentleman. If anything, I’ve always had a problem with the move to the hoop. Even as a young guy, when I’d go out with women, if they didn’t push me down on the bed, I was too stupid to go for it, or too willing to be rejected.

It’s All About How You Move Your Hips (And Feet)

Steve, 72: I was married once. That was a long time ago, and that was good too. But otherwise, for most of my life, I’ve been a bachelor. Right now, I have a really cool girlfriend. She’s 57. I’ve always dated a lot younger women — I attribute it to my immaturity. Also, I’m a fitness trainer and lead a healthy lifestyle, so I look younger than my age. But I sometimes think, ultimately, it might put a relationship at risk if the gap is too big.

My advice to guys looking to date: My social life is partner dancing — I’ve been doing it for years. All the Latin dances like salsa, bachata, tango and things you’ve never heard of. It’s an amazing social network, and if you wanna meet women, there’s a lot of single women. You meet a lot of cool people in general — guys too. That’s how I met my girlfriend. And that’s one of the reasons I didn’t do the online thing: You’re meeting a woman face to face. You’re right in each other’s face; some of these dances are super close, and it’s an instant test of chemistry.

When it comes to politics and etiquette in dating, a guy has to watch his step a little more nowadays in what he says and how he acts. But that’s more surface stuff. If you go deeper into what’s really important, it’s always been the same stuff: Basic things like how you treat people, you empathy and respect. I try to treat her right and be empathetic to her needs. That said, I’m still learning. I’ll always be learning. She’s basically looking to see, “Do you care?” And there are different ways of showing that. So if she feels that you care, if you’re showing her you do, you don’t have to really worry about the little details.

When it comes to sex, women become more assertive as they get older. A woman will sort of say, “I’ve been there, I’ve been there, I’ve been there, I don’t wanna go there, let’s see what we can do here.” I’ve been super lucky in that my sex drive hasn’t changed so far, and for my girlfriend, it hasn’t changed yet either.

I’ve studied Buddhist tantric sex. I’m a firm believer in it. I’ve been following it for 15 to 20 years and it’s really powerful. A buddy of mine turned me onto it. I was already into Buddhism, and it’s really cool, powerful stuff. I can’t explain it in a short period of time, but it’s about internal orgasms. The external is the ejaculation, and the internal is the feeling you get that can come internally — without the ejaculation. So if you learn this and practice it, it’s just amazing. It works for a woman, too.

Dating has always been hard, and it always will be. When I go out dancing, there are tons of singles, and so I see why this online thing works. There’s so many single people and so many people looking, and everybody more or less wants the same thing. There’s all these wants and needs and desires out there, then you throw chemistry into it, and it just makes it really complicated. I see people searching, searching, searching, falling down and getting back up again, and it’s tough.

I’m super appreciative that I’ve found somebody. If you want to attract the opposite sex, start doing things that are attractive to them. That saying, “Be yourself?” It’s actually, “Be your best self.” If you want to find a good person, you’ve got to be a good person.

You Can’t Relive the Past

Conor, 61: I’ve sort of tried internet dating, but not really. One time a friend helped get me set up on a dating site after I got divorced several years ago. But I never got on there. I hadn’t dated in decades, but the thought of meeting someone online never appealed to me. It felt too weird being out there on the internet that way. And I’ve never wanted to go to a singles bar.

I stay active — I belong to a tennis club, and do some volunteering. I’ve met women from those, and through different friends of mine setting me up. When you become single, you discover that a lot of couples you know want to set you up on dates, especially the wives of my friends. But the dates I’ve enjoyed the most are the women I’ve met on my own rather than the ones I’ve been set up with.

I’ve had a couple of bad dates with women. One, a person I’d already known for a while, seemed like she wanted to move things along a little quickly, and that’s just not where I am. I did go on one date with a much younger female, and there just wasn’t any chemistry. Most of the women I date are closer to my age.

Dating at my age feels informal. With women I already know, usually we get coffee or walk around somewhere for a first date. But I’ve gone on formal dinner-and-a-movie dates too. I was nervous for the first date I went on, a more formal one. It was weird after so many years, and I felt completely rusty. But after that, I’m a lot more relaxed about it. It’s not a big event that I get nervous for, like I remember feeling when I was younger.

I’m not in any rush to marry again — I like getting out and meeting people and doing things, which I’ve always enjoyed, but I have a lot more time for it now. Overall, I enjoy it. I’ve had a lot more sex since I started dating again — I’d say older single women really know what they want, and if they want to have sex, they’re pretty straightforward about it.

I don’t really worry about things changing. I went on a couple dates with a woman who was really fired up about the #MeToo movement when it came up on the first date, and we had a really good conversation about it — I’m supportive of it anyway.

Probably the worst thing I did was look up people from the past, women I knew or once liked. It was an experience! I chatted with a couple of them and it was nice to talk about old times, but we’ve ended up in really different places. Life changes us all. I look at it as a reminder to look forward instead of backward.