How Can I Do "Friends With Benefits" Without Getting Hurt?

Q: I was in a very long-term relationship and am now single, so I’m new to all the dating apps and to dating in general. After a few half-hearted attempts to date, I’m trying out a more casual setup —something more like “friends with benefits.”

Do you have any advice for how to best approach these types of relationships for a recently(ish) and not super experienced single woman? I’m trying to figure out how to protect my emotions or to maybe compartmentalize sex and intimacy, but I don’t really know what I’m doing. I’m afraid of getting hurt, but I also really want to explore these new experiences and learn more about myself in the process.

A: Just as I will stay up late tonight watching TikToks when I said I was “going to bed,” and Ben Affleck will drink Dunkin’ coffee, you, my friend, will get hurt.

Not because you’re a bonehead or an immature baby who can’t handle things, but because that is the whole deal with interacting with other people. The more contact you have with other people, the more chances you get for both joy and pain. Sometimes, I get upset when someone honks at me in traffic!

The biggest rule of casual dating is to do it until it’s not fun anymore, then walk away. You’re not always going to time that right, which can sting for one or both of you. But as long as you’re doing your best to treat yourself and others with respect, that’s OK.

Emotionally fraught experiences often go hand in hand with some kind of lesson. You might discover that you’re happier being single right now than you are dating, or you might find that one-night stands are not for you. Or you might be like, “Wow, I’m actually kind of in love with Barnaby.”

There’s no way to discover in advance what this phase of life might teach or give you. In fact, the lessons and gifts might not become apparent for a long time! So the goal must be to enjoy yourself.

If You Catch Feelings...

A lot of your experiences with casual dating are going to depend on certain immutable parts of yourself. For instance, by some mixture of genes and upbringing and probably the TV I watched as a teen, I generally don’t find sex all that intimate. I love it, but it doesn’t necessarily make me feel closer to someone. Maybe you’ll feel the same way. Or maybe that’s just not how you’re wired!

The hormone oxytocin — very subtly nicknamed “the love hormone” — is released when you orgasm, and it tends make people relax and trust others. So if you do wind up feeling more connected post-bang, that’s very normal.

Catching feelings doesn’t mean you’re “failing” at your casual-sex project. The point isn’t to neatly tuck away your emotions and never, ever feel anything more than sheer horniness for your FWBs. If it happens, you can of course tell them. You’re also allowed to create some space and pull back if you want to keep living in No Strings Land. You’re not going to win some trophy for Most Compartmentalized Person or Person Who Handled a Casual Relationship the Best.

What To Watch Out For

I will forewarn you, as someone who is a big fan of casual sex, there are some common issues.

1. If you like spending time with someone and enjoy having sex together, you might be like, “... This is basically dating? Should we just date? Are we dating?” Possibly! But, of course, remember that feeling that way doesn’t guarantee they’ll be on the same page.

2. There is a certain type of person who enters into casual relationships because they do not like being accountable to other people at all and think that’s the whole deal. It’s not! You’re still supposed to be a good person. If the situation looks like — in the words of relationship guru Taylor Swift — “a contest of who can act like they care less,” do not engage. If someone isn’t treating you with warmth, walk away.

3. We all crave affirmation, but if your interactions feel like a performance designed to win someone’s approval, that’s not a good sign. The casualness of the arrangement should invite honesty, not insecurity.

Check in with yourself as early and often as possible. Ask yourself things like “Am I still having fun with this person, or do I just want to impress them?” or “Am I developing feelings? Are they? If so, what do I want to do?”

If you see friends with benefits or casual sex as an enjoyable thing to do along with the many splendors of life’s buffet of choices, perfect! If, however, some secret part of yourself that you are trying to quell starts whispering “This could turn into something more” or “Maybe they’ll realize they like me,” you might want to rethink it or take a break.

That doesn’t make you uncool or not chill or something. It’s no different than discovering you’d rather watch Love Is Blind than Succession. The whole point is to find some kind of pleasure, whether from a friend with benefits or someone or something else entirely.

Please, sincerely, enjoy yourself — and stop if you don’t.

It’s A Pleasure appears here every other Thursday. If you have a sex, dating, or relationship question, fill out this form.