How to Have Casual Sex With Friends (And Not Regret It)

You're not getting emotionally involved, are you?
You're not getting emotionally involved, are you?Roman Maerzinger / Getty Images

Casual sex with friends can work. The trick is simple, really: Just don’t get emotionally involved.

“I’ve interviewed many adults through the years who had friends-with-benefits arrangements that worked well for them when they were single and looking for fun and connection,” says Andrea Syrtash, Relationship Expert and Co-Author of It’s Okay to Sleep with Him on the First Date. “The issue obviously pops up when someone in the friendship secretly (or not so secretly) wants more.”

Ultimately, casual sex isn’t all that casual, and there are a lot of factors we should consider before hitting the sheets with a friend. Here are some top tips from sex experts.

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Sure, sex can ‘just happen’ but make sure you are on the same page.
“[Sometimes] sex just happens. If it keeps happening, and one person may develop feelings, that’s when things can get awkward. Be clear and communicate the difference between friends with benefits, and what behaviors cross over to dating territory,” says Marissa Nelson, LMFT, Licensed Marriage & Family Therapist / Sex Therapist, Founder and CEO of IntimacyMoon Couples Retreats.

Set rules.
Set and agree to ground rules. “As an example, I suggest that both parties agree that neither will ask about nor tell the other about additional friends,” says relationship couch Jess Brighton.

Take responsibility for yourself.
“Before you sign up for a friends with benefits arrangement, be honest with yourself about your true intentions and boundaries,” says Dr. Jess, Astroglide’s resident sexologist. Ask yourself some serious questions: 1. How would you feel if you saw your FWB buddy out with another partner? If you can’t handle the fact that you’re not exclusive, say so from the beginning. 2. How will you approach the dissolution of your FWB arrangement? Eventually, one or both of you will want to move on; how will you feel about this when the time arises?

Never lie.
Even if it’s to accommodate your partner’s feelings. “If something makes you uncomfortable, speak up. If you change your mind about the arrangement, say so sooner rather than later,” says Dr. Jess.

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Re-evaluate when necessary.
There is nothing wrong with making and updating rules (e.g., no multiday sleepovers; no hard feelings if you cancel at last minute), but each situation is unique, so you need to discuss them on an ongoing basis.

When someone gets emotionally involved …
If anyone gets emotionally involved, the rules have changed and need to be evaluated again. As soon as emotions enter the equation, all bets are off. “My advice to anyone wrapped up in this practice is, if you are having sex with a friend and all you want is sex and friendship, if you ever decide you want more, sex needs to stop. Otherwise, you will lose your friend, if not permanently, definitely, temporarily,” says Dr. Elaine Stevens, CRS, Board Certified Relationship Specialist.

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There also has to be transparency and accountability to the friendship.
“This is not someone on Tinder who if your not feeling them anymore you can just swipe left or ghost them. People can get themselves in trouble by not remembering that they are friends first, so there is a certain respect and consideration that goes with it,” says Nelson. Remember, this is supposed to feel good, be fun and pleasurable. “Fantasize together, role play, use toys and all the sticky, fun stuff — and know that you’re safe to indulge your sexual desires because you’re doing it with a friend you trust,” says Nelson.

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