How to date as a man in your 30s

It doesn't have to be a nightmare.

A few caveats before I get into one of my favorite subjects. First, I’ll be 40 in October, but the last time I rode the dating emotional rollercoaster was in my early to mid 30s. I learned some stuff that really worked.

Also, I’m married now and haven’t dated in nearly five years. I don’t know what the kids are doing these days. Is Hinge still for serious relationships and Tinder for situationships? I don’t think it really matters. What I’m going to talk about are principals that can be applied to any dating context.

Also, I’m a straight man who learned how to date in a way that worked for me in a city. I wasn’t dating in the burbs or rural areas. I wasn’t divorced and didn’t have kids. I wanted a serious relationship and wasn’t looking to hook up (though there’s nothing wrong with that, as long as you let them know it’s what you want). I had a constant flow of new women to date because where I lived back then, Washington, D.C., has one of the highest percentages of single people and highest ratios of single women to men. You’re probably in a different situation, but again, I think what I’m going to say can help.

Let’s begin with the dumpster fire that started it all.

I was a couple years removed from a long-term relationship that had ended with a rough breakup (and had spurred me to start going to therapy). I was on the apps, particularly Bumble and Hinge, because I wanted something serious again. I’d fool around with Tinder here and there when I was lonely, but that never really satisfied me. I was in my early 30s and tired of being alone.

We’d matched on Bumble and met for drinks and dessert at a really good Filipino restaurant near my house. My first reaction seeing her in person was, How’d I convince this person to go out with me? She was gorgeous and cute and smart and super into me right away. I learned she was a stage actor, which was a huge turn on. I learned her family had immigrated from a socialist country, which led to interesting and heated conversation. Everything was clicking—we were clicking. But that suspicious voice kept whispering in my mind: I don’t know, man, this seems too good to be true.

We ended up making out across the table at a tequila bar down the street—something I tried to never do on the first date (more on that in a minute)—and she asked to come back to my place with me. I don’t know if it was all the tequila or that voice telling me something was off, but I said I was tired and that we should meet up again soon.

Soon was a few days later for a quick lunch on a workday, and this time I took her back to my place. The sexual energy was off the charts. It felt like she wanted me more than any woman ever before. We ripped our clothes off and messed around for what felt like 30 seconds before she asked me to get a condom. I grabbed one from my nightstand and ripped the package open.

That voice popped in my head again: She’s so hot, man, don’t screw this up. That must’ve thrown off my flow, because when I went to put the condom on, I’d gone soft. I tried to get turned on again. I touched myself in the way I do when I’m alone. She said some sexy stuff to help out, but my body wasn’t responding. I tried to act cool and said it was the condom’s fault, but shame flooded my body. I felt like a failure, an imposter, not as manly as she thought I was. She was kind about it, not saying anything to add to the shame. I walked her out of the house, and she said we should get together again soon. But I knew something was wrong. I knew I’d screwed it up.

We tried to have sex one more time that weekend and it happened again. My body shut down. Things got awkward. She was super cool about it again. She said that it didn’t change how she felt about me. But later that week brought the final verdict. I’d, in fact, screwed it up. She told me we should be friends. It was over.

I was so sad and embarrassed. I was terrified that I was broken in some way, like I’d watched too much porn over the years or had permanent erectile dysfunction. I told a few close guy friends about it. I doubled down on therapy, joining a men’s group with others having relationship issues. I finally admitted to myself that I didn’t automatically, naturally, effortlessly just know how to date and be in a relationship. I accepted that it was okay to get help.

My therapist asked me what I wanted in a partner. I fumbled through some answer about the perfect combination of hotness and common interests. What the question exposed was even though I’d been wanting a serious relationship so bad, and even though I was saying that looks didn’t matter as much as personality, a part of me was still invested in scoring a hot chick. This part of me was stuck back in high school trying to impress my buddies. This inner lonely 15-year-old thought having a traditionally attractive girl on my arm would get me the attention I so badly wanted back then—and still wanted.

I realized that as a man—particularly a straight one, since that’s my experience—it’s the default to overly focus on appearance.

We’ve been blasted all our lives with images of Photoshopped, makeup-caked, minimal body fat yet curvy women’s bodies. We’ve been told that emotional intimacy is for women, “soft,” and “gay.” We’ve turned to masturbation with porn to relieve stress so many times now that our brains have been rewired. That’s often where my mind went back then when around women or scrolling dating apps. I overlooked the stuff that really makes or break a relationship, like a sense of friendship and shared values.

As I started dating again and processed more of my feelings with my therapist, I came up with a way to remind myself of what about a partner really mattered to me. Hotness was still important, but not more important than other variables: emotional connection, friendship, values, spirituality, and future plans (having kids, etc.). I wanted someone who was able to have potentially difficult emotional conversations without shying away from being real and honest with me. I wanted someone I could laugh and be weird with. I wanted someone who shared my belief that our society’s political and economic inequality is a problem. I wanted someone who shared my awe in nature and the unknown. I wanted someone who had similar long-term plans.

Having what I truly wanted in mind helped me slow down and stay patient. Dating became about finding someone who checked my boxes rather than trying to get hot women who liked me to keep liking me. Setting boundaries became easier, like committing only one hour to first dates and kissing only if I really wanted to.

I started noticing that on some dates I’d still be fixated on looks when I swiped right. She had big boobs or a nice butt or a conventionally gorgeous face, and I didn’t care too much about the rest of her profile. Those dates were usually the worst. The conversation felt forced. The energy was awkward. That little inner teenager part of me felt pressure to impress. But I was aware of it. And because I’d only committed an hour, the discomfort didn’t last forever. If I was feeling brave, I would tell them at the end of the date that I was feeling more of a friends vibe. Most of the time, I’d hug them goodbye and text afterward that I wasn’t feeling the chemistry.

When I had sex again, my body worked! She was hot, but I wasn’t feeling all that pressure inside. I’d moved slow and made sure there was emotional connection first. It didn’t feel forced and instead unfolded organically. After a few months, she decided there wasn’t the chemistry she was looking for. It was disappointing, but it didn’t hurt all that bad. I was confident that if I stayed patient and focused on what I really wanted, something good was just around the corner.

Then I met my future wife, who’s hot and checks all the boxes.

The other day at a therapist conference, I met a woman who I found super attractive. I felt that familiar freeze hit my body and heard the teenager getting excited in my mind. I laughed and thought to myself, “Ah, there you are, buddy. You really think she’s hot, huh?” Because that teenager is part of me, he’s never going to go away. I’ve just changed how I relate to him. I don’t let him run things, but I also don’t ignore him. And what’s really cool is, because I refocused on finding a partner who can handle emotional conversations, I can bring these kind of experiences up with my wife. She can handle it, and being real with her makes our relationship stronger.

I’d love to hear about your relationship to dating, even if it was in the past—what’s worked for you, what’s been frustrating, what are you hoping will help you get the relationship you really want?

— Jeremy