Illustration by Maria Ines.

Illustration by Maria Ines.

It’s Friday night, and you’re out with your squad playing miniature golf or gorging on popcorn at the latest screening of The Avengers. Suddenly and unexpectedly, the moonlight hits your friend’s hair just so…and you feel your underwear dissolve. WHAT just happened to you?! Maybe that friend of yours is really hot and you’ve always wondered what they’d look like in their birthday suit, or perhaps you’ve before never thought of them in That Way—whatever the case, you now find yourself unable to shake the thought of eternal boneage with their bod. These thoughts are totally natural (and definitely sexy)! If you want to pursue them in reality, maybe a friends-with-benefits situation is for you.

I didn’t begin regularly hooking up with any of my friends until I became an adult, save for a makeout buddy or two in high school. It’s not that I was necessarily opposed to the idea—I just never realized that it was an option. I qualified sex as an exclusive within the context of a bona-fide romantic relationship, OR a one-off adrenaline-fueled encounter. I wish that I had allowed myself to get it on with pals a lot sooner, because it’s a lot of fun! Some of my best sexual experiences have been with trusted friends who made me feel sexy, comfortable, and cared about. I didn’t need to love them in order to bone them: Our friendship was enough to satisfy me emotionally.

That being said: I’ve gotten myself into some tricky situations as the result of hooking up with a few of my dudebros. I really, really want to tell you that friend hookups are easy. That you can just hop in the sack and do your thing and give each other high fives afterwards. For the most part, this is totally the case! But there are definitely instances where hooking up with a friend becomes a katamari of feelings, and you’re suddenly spiraling around picking up things that don’t belong together. Despite my affection for the many “benefits” that friends can provide, I want to talk about the various doomsday scenarios that can take place if you decide to have sex with a pal. They are real, and I want you to be prepared!

Boundaries

After you have that first big talk, there’s one more discussion to introduce. Just because this person is your friend—presumably someone whom you know and who knows you well enough—does not automatically mean that they will respect your sexual boundaries, or even know what those boundaries are. Outline the terms of your hookup: What are you cool with? Keep it simple and honest! You may choose to keep things monogamous, e.g., not hooking up with other people while you two are getting it on. Many people also opt for a no-strings-attached thing, since this model is not a romantic relationship. This means that you both have no obligations to each other, and have the freedom to do sexy things with other people. Go over your needs and desires, your dislikes and boundaries, and be sure that your pal does the same.

Keep it light if things get weird

As far as the actual action goes: It will probably be strange at first! You’re creating a totally new aspect of your friendship, and that can feel weird. Sure, it’s hot when unresolved sexual tension is resolved. It can also be a serious giggle affair that goes, like, “Oh my god, do you REALLY have a birthmark shaped like a cactus on your butt?! THAT IS SO COOL!” So the lighter you can keep things at first, the less awkward it will be. And if it does feel awkward? Just acknowledge it! “Hey, this is kind of silly and awkward, isn’t it?” is a good first step to clear the air, so you can move on and get down to what is really important: the makeouts!

Weigh the potential outcomes

If you deeply value the friendship, understand that introducing hookups to the mix can make it hard for a friendship to continue. Which is more important to you? There is no right or wrong answer. One of the reasons for this: JEALOUSY.

Assuming you have not agreed to be monogamous, you may have to see your friend dating other people while they are hooking up with you. This may make you feel very uncomfortable! The green-eyed monster can show up whether you want it to or not. Luckily, jealousy is one the few emotions that can be reasonably rationalized away…somewhat. You have to remember that your friend is not romantically obligated to you, and they deserve to find love just like you do.

That can feel so tough, I know. In high school, I regularly indulged in kissing dates with one particular friend, and although I didn’t Like Him Like That, it was still sucky to watch him flirt with other girls at school. I hated being jealous, but I couldn’t help it! Eventually, the only thing I could do was to put a hold on our trysts until I was able to reconcile my brain with my heart. I was able to work through my icky jealous feels by writing in my diary a LOT, and telling myself repeatedly that we were pals and NOT romantic partners for a reason: We had nothing in common and had no love chemistry at all. It took some time, but once he started dating a girl I knew (and liked!), I realized that I have no ownership over my friend. But I also realized that the opposite was also true: He had no ownership over me—and I felt totally OK about that.

Stay alert

Take stock of your feelings every so often. When you hook up with a friend, your relationship to that person changes. I wish I could say that things will stay just the same, but that’s a little unrealistic, and you should know that before makeouts commence. When hooking up with someone, you are getting to know them on a much more intimate level: physically, for sure; emotionally, also highly likely. Sometimes that intimacy can be easily mistaken for LOVE FEELINGS, even if you decidedly are not in love with your friend. Once sex-related fun is in the mix, it has a funny way of confusing your emotions, because (hopefully!) you are experiencing a caring, tender connection with someone who is being nice to you.

Liking someone also means liking them on the whole, as the difficult, complex person that they are. It means that you can’t stop thinking about them, that seeing them in the hallway at school makes your heart skip a beat. Being sexually attracted to someone is only part of being attracted to them as a full, unique weirdo person. If you start feeling lovey-dovey toward your pal, ask yourself, Am I falling for this person because we are hooking up, or are we hooking up because I am falling for them? Don’t immediately assume that you are falling in L-U-V unless you are absolutely certain.

What about love?

What happens if you do fall for your friend? This, my dear cherubs, is a tale as old as time. No need to hit the panic button! We are going to work through these complicated feelings together.

First off, this is known risk in hooking up with a friend. It important to note that it is a risk you’d run anyway, regardless of whether you bone or just cuddle on a couch watching The Fifth Element. But physical attraction can speed up that process, or make the unrequited feelings sting that much more.

Ask yourself: Will continuing a sexual relationship cause you pain and sadness? Are you convinced that sleeping with this friend will cause them to love you back? I can’t answer these incredibly difficult questions, but I can urge you to consider them, and take all the time in the world that you need. Though the answer to the last question is probably a resounding NO. Agreeing to get with someone physically is not the way to get them to like you, and it really sets you up to be saddened even further. The best way to catch someone’s eye is by just being your very rad self, by being the megawatt starlet that you are. YOU ARE A CONSTELLATION OF AMAZING!

Just friends, once again

You are free to stop the arrangement at any time, for any reason. You are also free to pull the plug on the entire friendship, if you feel that you need to preserve your happiness. Maybe you still can’t reconcile your jealousy (which is totally OK!), or maybe you’ve begun dating someone else and it just feels weird, or maybe your friend isn’t treating with you with the respect you deserve. You do not need to worry about being polite or hurting someone’s feelings. What matters is your emotional health! If that means you don’t feel like you can be friends anymore, that is totally OK.

In a one-on-one romantic relationship, you make an agreement with someone to exercise certain boundaries over how you engage sexually with others. Whether that is 100 percent monogamy, or totes open, or anywhere along the spectrum, there is a pact that is made. When you hook up with a friend, you generally don’t have the security of that pact. It can be difficult to feel truly sexually comfortable without that sense of insurance. If this is something you need, you deserve it, and you should go looking for a person who will give you the comfy warm security feelings that you are entitled to.

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Hooking up with a friend has numerous advantages—chiefly, that you aren’t in a relationship with this person, and are FREE AS A BIRD. You have the convenience of exploring your sexuality, without the added extra layer of feelings that you may not need or desire right that second. You deserve to have the sex-related fun that you want, and maybe that means you want it from a pal. And as long as they are down, and you talk about it and understand the emotional risks involved, go for it! Have all of the sexy friendships that you want. ♦