Should You Ever Have Sex on a First Date?

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Ryan O’Connell is a New York-based writer. He likes shoegaze, the Olsen Twins, and figuring out why people do the things they do. Oh, and he tweetsCheck back each Thursday for his latest Call Your Boyfriend column. (You KNOW you have a question. Send it to Ryan.)

I always hook up with people as soon as I can. Sometimes, I fear I do this because I feel so disconnected in the dating world. The rules are always changing, but this one about no-sex-on-the-first-date seems to be holding strong. Maybe we both needed to just get laid? Or am I making excuses for myself?


Dear Sex ASAP,

I would never tell someone, “YOU CANNOT HAVE SEX ON THE FIRST DATE. OTHERWISE, A GUY WILL NEVER RESPECT YOU BLAH BLAH BLAH.” Because while it’s true that many men still grapple with The Madonna and The Whore complex, you should never change your behavior to accommodate a man’s ingrained slut-shaming.

That being said, it does sound like you’re having sex with these dudes for the wrong reason. (No judgments! You can have all the sex with whoever you want for the wrong reason. I do it all the time!) You said it yourself: “I do this because I feel disconnected in the dating world.” That tells me that you’re boning these men not because you LOVE sex — you’re doing it because you want to feel close to someone, albeit for a brief fleeting moment.

The problem is, sex doesn’t work that way. One of the first things I learned about sleeping with someone is that once the orgasm fades, it can actually make you feel more alone than you were before. It took me a while to learn that there are a variety of ways to feel connected to someone without having them inside of you.

Clearly you don’t like this habit of falling into bed with strangers. Otherwise you wouldn’t be writing me! Your question was brief so I have to surmise some things. Here’s a guess: what you really want is a relationship and a meaningful connection with someone, and you’re doing the insta-sex instead. And the result is that a lot of these guys aren’t calling you back after you’ve slept with them, so you feel empty and alone, so you go out with another guy, repeat cycle.

I understand your frustration. If what you truly want is to stay single and get laid, then more power to you, babe. You’re entitled to have all of the sex with all of the men. However, if you keep on feeling like shit afterward and wishing you had something more substantive with someone, you should try taking a different route.

Whenever you find yourself hitting the same wall over and over again—whether it be with friends, lovers, or work—you need to reevaluate the things you’re doing and try to mix it up a bit.

Here’s how I approach hooking up with someone new. If I go on a date with a guy and don’t really feel that much of a connection with them beyond physical attraction, I will hook up with them and give all the BJ’s because…I don’t care. Like, I saw their naked brain and was like, “Not a fit for me,” but now I’m totes cool with seeing their naked body for one night. And then I don’t give a shit whether they text me afterwards or not. (Note: This relaxed attitude can lead to feelings of crippling emptiness once the sex is over. Proceed with caution.)

If I have a really good first date though, I don’t want to sleep with him. I want to drag it out. I want to make out with him, say good night, and then dream about his penis all night long. And then I want to text him the next day and be like, “Hi. Let’s hang out again.” And then think about all the parts of his body I have yet to see and explore! Basically, I want something to look forward to. I want a sense of mystery and wonder, so that when we finally do unveil ourselves to each other, there’s a natural closeness between us that has already developed and will only be enhanced through sex.

But, you know, that’s just me! The thing is, it very well might be you too. At least it sounds like it could be you. If you’re worried that you’re making excuses for jumping into bed with people so soon, then chances are your heart and vagina aren’t really in it. If you don’t like the way your behavior pattern feels, fix it. Take things slow. Make small changes. Put structures in place to prevent you from sleeping with a guy on Date Numero Uno. Whenever you find yourself hitting the same wall over and over again—whether it be with friends, lovers, coworkers, neighbors, the list goes on—you need to reevaluate the things you’re doing and try to mix it up a bit. We humans always blame our issues on something external, something less tangible, when really, sometimes all it takes is just a change in your thought patterns to get to where you want to be.

Dear BF,

I am 25-years old, single, and living in New York. Should be a blast, right? Ha ha, um no. After college, all of my close friends magically got boyfriends and now I’m the only left on the prowl. I don’t get it. Weren’t my 20s supposed to be a time of getting footloose and fancy free with my friends? I didn’t expect to feel like a cat lady until at least 30. What gives? When did being single at 25 feel like being single at 35? Also, how do I enjoy being alone without feeling so damn lonely?

-Too Young To Be This Pissed About Being Single 

Hi Too Young!

Last night, my friend and I had this same exact conversation. No joke. She said to me, “When did going out just become about desperately hoping that you meet someone?” It’s true. When did that happen? In college, you’d go to a house party, rolling deep with an entourage, and you’d be all ready to have a blast with your friend soul-mates. Of course, you’d secretly hope to hook up with the babe in your Feminist Lit class at the end of the night, but if you didn’t, NBD. There was always the next house party. Or the next one. There was no sense of urgency. Three years ago, you had all the time in the world. Now, you feel like you’ve got nothing. The change is that quick, isn’t it?

There is no way to not feel lonely when you’re single. It just happens, and then you have to ride the emotional wave (but not for too long, because eventually you’ll wipe out in front of a pint of Ben & Jerry’s). Often, we try to run away from the internal brutality of loneliness. About two years ago, I sort of retreated into my cave and threw myself into my work, avoiding any and all potential romance with boys. There was NO balance in my life. All work, no play, and after awhile, I thought I was going to go insane. Eventually, I had to make a conscious decision to leave my bed and actually start going out and having fun. Once I did, the “yayyy!” level in my life increased 10,000%. Sure, I wasn’t meeting the man of my dreams (and I won’t lie, I was still a little bummed out about being single) but at least I knew I was putting my life in motion. The rest, I trusted, would take care of itself.

So go the hell out. Say yes to everything you’re invited to. Seriously. Being single is about not wasting any potential opportunity. Not because you might meet your future life partner, but because you need to have a fulfilling social life. YOU NEED TO FILL YOUR LIFE WITH JOY. YOU NEED TO GO TO SOME RANDOM HOUSE PARTY IN BUSHWICK BECAUSE WHY NOT? YOU’RE FUCKING SINGLE.

You should probably use this time to get to know yourself. Like, take YOURSELF out on dates and be like, “Hey bitch, why are you so damn crazy?”

Also, as corny as it sounds, you should probably use this time to get to know yourself. Like, take YOURSELF out on dates and be like, “Hey bitch, why are you so damn crazy?” I’ve learned A LOT about myself in the last two years, namely that I’m crazy and suffer from intimacy issues. I know this about myself now, and I can choose to put these issues aside so they don’t get in the way and make me miserable — I have my time alone to thank for that. I am now “working on myself” (ew, I hate that term, but there’s really not a better one) and essentially getting my shit together. Why? Because the better of a person you are, the better of a person you attract. I dated psychos in college because I was a psycho. Hopefully the next person I date will be the bee’s knees, because I’ll be the bee knees.

I know how hard it to see your friends eclipse you in the relationship department. All of a sudden, you don’t feel as emotionally mature as they are, and you can’t relate to their lives. But listen up: you are not defective, you are not a loser, you are not unlovable. Being single means none of these things — really! I swear! Just focus on yourself and have the most amount of fun possible. NOTE: having fun when you’re single does not have to mean screwing everything that walks and having a permanent hangover. It can mean discovering what you really like to do or taking trips or getting obsessed with yoga and kale and whatever else healthy single people do. It means becoming the person who you’re going to be forever.

All of my parents and grandparents look at me and say, “You’re so young. The world is your oyster. Enjoy it!” It’s been expressed to me a thousand times that my twenties could be the best time of my life. While I hope that’s not true, I take what they say to heart. If you’re 25 and already feeling like an anxious, depressed cat lady, you might just be doing your twenties wrong. Get it together. Drink up your youth and chase it with vodka (followed by water and electrolytes! You aren’t 19 anymore!). You don’t want to regret anything. Trust me. You are too young to feel this hopeless. Get it together, sister.