I Started Dating Like a Man—And It’s Working for Me in 4 Major Ways

They may actually do some things right.

“I think you’re incredible but I don’t think I’m actually ready to have a relationship with you.”

The man who uttered these words to me was the guy with whom I had just recently enjoyed a very hot first date. The lead up to it was terrific as well. We “got” each other. Neither of us were into the whole Good morning, Beautiful, every day texts or phone calls; we spoke and messaged each other a few times after we connected online and casually let the buildup carry us along to meeting in person.

When we saw each other face to face, it was pretty magical. We had a three-plus hour date during which we talked a lot of shop (he was at the tail end of a very complicated divorce), and covered a ton of super ridiculous subjects like completely non-PC album titles from long-gone punk bands (the R-word? Really?) and what to do when your married neighbor shows up in your online dating suggestions. We laughed and flirted our asses off and the kiss goodnight at my car, as well as the follow up over the next few days while we planned our second date, was effortless and exciting. 

Then he went on an eight-day road trip with his kids. 

“I think he’s underestimating how difficult this divorce is gonna be on his children,” I remarked to a friend, after getting a, whoa this is hard, text from him halfway through his trip. 

“Does that scare you?” she asked me. 

“Nah. I’m dating like a man these days. It’s all fine,” I answered. 

I’m in my 50s and have navigated two marriages, several multi-year relationships, and many, many dates. But I decided to take a break from dating last winter after ending a relationship that had grown stale, and exhaled into Girls reruns, endless pajamas, and lots of drum practice. I had hoped to clear my head by doing nothing much more than relaxing into a cozy slothdom—and it worked. 

I decided to rejoin the dating pool this summer, but something was different. I told myself that if I was going to start putting myself out there again, I was going to be way less invested in the outcome, or even the income. Great chat and then he said he’d call me and he didn’t? Fiiine. See ya! And then it occurred to me: I’m going to date like a man. 

Even though much of what middle-aged men do leaves us scratching our heads, clutching our pearls, or even howling at the moon, I have to say, when it comes to dating, a lot of their typical, charted behavior? Well, it lands. 

So, without further ado, here are four ways I am currently dating like a man:

1. Men move on easily.  

Let’s go back to my Great First Date Guy. Ahead of his I’m not ready line, he shared some observations from this road trip with his kids, including how they were teary-eyed and glued to him 24/7. He also shared with me that all of this was semi-triggering issues around his long-term sobriety (a definite red flag for me, but I listened and did not interrupt). 

When he was done talking, I said, “This all makes sense to me. Thank you for sharing that. I’d be lying if I said I wasn’t disappointed because we had a great time and we have great chemistry, but I hear you.”

I stopped speaking—I think he was waiting for me to continue and then realized I had in fact said my piece. “We did. We do…” his voice trailing off. 

“Yeah, so, all the best. I hope you get the kids situated and just as importantly, that you take care of yourself, OK? Bye.” 

And I hung up the phone. I did not default to a place where I know many of us have found ourselves before—including me—starting a rambling soliloquy of why we can work this out, and how flexible and chill I am. This time around? I actually am that chill woman and will not stick around. Next!

Straight guys our age (yes, there are exceptions of course) do not jockey to be “picked,” do not make their case for why this love affair deserves a chance after a woman says “not for me,” and do not try to prove their “value” as a supportive partner. They just move on. 

It’s a no-nonsense and easy solution. I feel completely at peace with it because, also, like many men, I know there are plenty of other people to date. Later that same afternoon, I got a voicemail from a guy I met a few months back saying, “You’re probably screening your calls from this unknown number, so if you even remember me, I finally picked up your card and wanted to reach out. I’d love to chat if you’re available.” 

You know what I did? I picked up the phone and called him back. We’re having dinner next week. I also didn’t waste any energy half-jokingly (passive-aggressively) teasing him that he sure took his time. Because, who cares? Men don’t care about that shit. They’re either down to connect, or not. 

2. Men date more informally, with the idea of having casual sex, more than women. 

This is not something I’ve just made up in my head, there’s plenty of research about how middle aged men and women date to back up my new ‘tude, including a survey taken by 298 heterosexual current dating app users (41.3 percent women, 58.7 percent men), aged between 25 and 50 years, which found that men think about casual sex a lot more, well, casually. 

With both First Date Guy and Picked Up Your Card Guy, casual sex was/is not off the table. Yes, I am looking for a relationship but I’m now less invested in a timeline of how it might happen. Like a man, I don’t believe that if we have sex on the early-ish side of dating, that means it will stay casual or become some dreaded situationship. 

Just for fun, I polled 10 random men, four of whom are single, and asked them, “Does sex early on mean it’s just a hookup?” Each of them said something along the lines of: “No, it means it’s sex with possibilities unless someone states otherwise.” If you’re open to fuck and that’s all, it will stay casual.

They all agreed that if you say you want a relationship, and then have sex after a few dates, a good guy—even a good guy who isn’t entirely sure about what he wants—won’t keep fucking you if he’s just into hooking up. 

That sounds imminently reasonable to me. First Date Guy and I had a get-together on the books for next week ahead of our conversation and I already knew I was going to have sex with him if the opportunity presented itself. That one thing doesn’t knock the relationship potential out of the box. In our “ending it” phone call, he told me that he knew I was looking for a relationship, and though he thought he was too, he’s realized he’s not. So, like two men, we basically shook hands and parted ways. 

3. Men try on different potential partners with more frequency than women.

Another fact pulled from the data that is paying off for me in a way it never has in the past, is this idea of dating multiple people at once. As soon as I was ready to start dating again, I was talking to two and three men at a time, sometimes going on multiple dates each week. And if one of them asked how many men I was seeing, I never lied about it.  

On our second date, a guy who seemed far more interested in locking it down, asked me if I was planning on dating other people. I said yes without hesitation. He didn’t freak out; rather, he said, “OK, I guess you need to experience other people. I know what I want but take all the time you need.” 

That wasn’t a reverse psychology attempt at winning me over, nor was it some lame-ass strategy by me to make him jealous and commit faster. I was honest. He was honest. It was, again, just a straightforward interaction that seems to speak to the way men work.

How many times have you heard a girlfriend get really worked up about something a man did that went against the grain of what she wanted? Often, said man had just told her how he rolled, and she decided not to listen. She just superimposed her own desires and assumed it was all shiftable. In this new head space, moving slowly and carefully is how I want to inch towards a relationship. 

4. Men spend more time on the apps.

The final point in the research was about how men traditionally spend more hours a day on dating apps than women at our age. For that, I had to check in with the dozen or so single people I know—men and women—to see if my own current instincts on this were male-centric, or not. 

“I’m online but there are a ton of guys who just start conversations and then peter out, as well as guys who ask you for your number far too quickly and then tell you their whole life story, because they’re lonely,” my friend T, a single woman who is on the apps but mostly just finding her inner peace after a long and challenging relationship, told me. “So, I’m disenchanted with the apps and probably don’t check them as much as I should.”

But from my friend C, a single man who is online every day: “It doesn’t really matter if I see anyone I like or not, I’m just looking,” he says. “Sometimes I don’t even know what I like. It’s just another form of mindless scrolling, with the unexpected reward of seeing someone intriguing on occasion.” 

Ding! Ding! Ding! I have a feeling that when C. does make a connection, it seems somehow more meaningful for him, because he’s not hoping for a solution to his relationship vacancy. Rather, he’s just looking around. That’s me too. 

Even with the state of the world and cesspool in which we find ourselves sloshing around these days—much of it all men’s doing—I have to admit, my love life is much tidier, and possibly even more expansive, since I started dating like a man. Now if only our world leaders would do the opposite and lead like women…

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