Awkwardette's Ill-Advised Guides

Awkwardette’s Ill-Advised Guide to Getting it On: How to Survive Doing a Friend

We’ve all probably watched way more romantic comedies than we’d like to ‘fess up to. Truth is, romantic comedy is my favorite genre. It was good enough for Shakespeare and Tennessee Williams (The Glass Menagerie is a romantic comedy, right?), so it’s good enough for me. One problem: as much as the When Harry Met Sallys of the world make me laugh and feel giddy and good inside temporarily, they fill my brain with an impressive amount of bullshit. I’ve had to unlearn a lot of this bullshit, especially in 2011. 2011 was a particularly difficult year for “friends with benefits” learning, and I’m not even talking about the creepily similar J Tims and Ashton Kutcher vehicles on the subject that both came out this year alone and were so rife with terrible advice and false ideals that I can’t even really address it further – so here is my attempt to set us straight on doing it with friends.


I hate giving rules because they were often made to broken, but rules are useful for one reason: they set boundaries. And if you’re fucking your friend, you obviously have an issue with boundaries. Rules are important in this regard, or else someone can get hurt. No, no, someone will get hurt way more than they already will, because face it, heartbreak in this situation is inevitable.


Rule #1

Gauge whether or not having a friends with benefits situation is a good idea or not.

In real life, Harry and Sally probably would have gotten weirded out permanently and would have never have ended up together, but that's okay.

Okay, hook ups happen. This shit can often be buried and forgiven (never forgotten). To continue the situation means there needs to be some deliberation. Some questions need to be asked of yourself before you dive right in.


1. How good of friends are you? There’s more than one type of friends with benefits arrangement

a. Friendship starts with the arrangement. This means you start sleeping with someone under the guise that no relationship will begin. It’s not the same as no strings attached (NSA) – there is a difference, in my opinion. No strings attached is as casual as you can get, and you pretty much just meet up to fuck. Friends with benefits will do things like hang out, or go to parties together, and might even date but with no intention of it ever developing into something more. Most people think this is ideal, but it also has its pitfalls that we’ll get to later.

b. Casual friends/acquaintances that turns into sleeping together. You already knew the FWB. They were a friend of a friend, someone from school, or anyone you don’t really know that well. You may not even have been on Facebook-friend terms yet. This also may seem like an ideal situation. Let me reiterate – there is no ideal situation. You may not have too many attachments to this person, but you may be attached to people that do. Are you going to be able to avoid this person if things get awkward or weird? How often might you run into them? How entrenched in your social life are they really, even if you’re not close to them? Do you want to risk that awkwardness? One plus &mdash if you do have mutual friends, you can do a little research on the person, get some background information if that’s your thing.

c. Good friend turned FWB. This is, by far, the most complicated of all FWB situations. This is someone you hang out with, that you’ve had heart to heart discussions with. This is someone who has some serious dirt on you, and someone who you know an awful lot about. This is difficult. There is absolutely no way I think you can sleep with someone you are good friends with without having some feelings for them. And I am not specific on what kind of feelings; perhaps they won’t be romantic, but if you are sleeping with a good friend without feeling something, you are a robot, and you do not need to read this guide. Before going down this route, understand that once you sleep with someone, the dynamic and relationship is immediately changed. You might not be in a relationship, but you are not just friends. Don’t delude yourself. It’s not possible.

2. Are you willing to lose this friend? Because if you sleep together, you will lose this friend. The entire dynamic of the friendship will be different. But change isn’t always bad, so this is really up to you to decide whether it’s something you want or not. Is this someone you can’t imagine not going to about relationship and dating problems? Is this someone you just cannot imagine life without but one of you is waffling on the idea of having a committed relationship? Don’t sleep with them. If you hook up accidentally or purposefully and have regrets, recon work means figuring out how you both can move on past that and become as close to “just friends” as you were before; this means no sexy times.

3. Will sleeping with this person hurt someone else? Sometimes when you start to date a friend, it makes other friends a little uncomfortable. That’s fair. I think that’s something you work out with your friends. If this person might be someone you want to commit to, then I think it’s worth the work of finding a compromise. Is something that isn’t worth the work of a relationship worth the work of making sure all of your friends are cool with it too? This is especially important if you have mutual friends. Don’t make an uncomfortable situation for the people you care about just so you can get your rocks off. There’s too many other people you could be sleeping with instead.

So you’ve assessed the risk, and you’ve decided to go for it. Now what?

Rule #2

If you think you are developing feelings, stop, stop, stop, stop, do not pass go, do not collect $200.

Here’s the thing: sometimes these things are not as black and white as “we are friends, and we have sex.” They rarely are. In fact, it’s very well possible that your friend may have feelings for you. You cannot guarantee that they don’t; you cannot guarantee that they do. The only thing you can guarantee is that what you have is all your friend is wiling and able to give you at the moment, or else you would have more, right?  I mean, unless you’re the commitment-phobe who started this whole mess. In which case, go for it, I guess, but if you weren’t sure before, what makes you think you’re so sure now, huh?

No, for real, STOP IN THE NAME OF LOVE, for real.

Whatever you do, do not try to fool yourself. Do not tell yourself that if you sleep with him/her, they will suddenly want a relationship. In fact, if someone has feelings for you and is suggesting a friends with benefits situation, there is something going on with that person that has little to do with you. They are not capable of a relationship for whatever reason at the moment, and so the increased intimacy will probably only make them uncomfortable and cause them to act weird. That’s not on you, but just know that you cannot fuck someone into loving you.

I am not saying you should necessarily tell your friend you are developing feelings. It really depends on a few elements. What do you hope to get out of telling your friend? Do you hope they will respond with similar feelings? Are you prepared to be very disappointed with their response? Let’s look back at Rule 1.2. Are you okay with losing this friend? Because telling your friend that you have romantic feelings for them, no matter how strong the friendship, may result in that. Not telling your friend also may result in that. In many ways, you are kind of SOL.

What you do with your feelings is kind of beyond the scope of this article, but I can tell you that you should no longer continue sleeping with your FWB so you can get a chance to sort out your feelings. Who knows, maybe you don’t even have as strong of feelings as you thought! I’ve definitely started developing what I thought were feelings, but then I took a few weeks away from my FWB and realized it was all probably oxytocin playing mind games on me. There’s so much that goes on biologically that you have no control over when you have sex –time away from each other can help you see through the sexy, friendly fog.

Rule #3

Fulfill the friend part in order to cash in on those benefits.

You don’t get health insurance if you don’t show up to work, folks, so no hanky-panky unless you can play Words with Friends and maybe check out that movie you want to see like adults, without it getting weird. If you can’t hang out and interact like normal people, this is a bad idea and it will only get weirder.

I wish.

If you weren’t really friends to begin with or at least weren’t that close, you are not exempt. Go out for a drink, go out for dinner, for gods-sake, see sunlight together. It’s the least you can do for each other.

But really, I think this rule is way more important for those of you who are in the sack with someone you’ve been thick as thieves with for awhile. You want to remember that you can maintain a friendship with this person on a non-sexual level. You want to remember how to interact with this person without sticking your tongue down their throat. This also helps prevent anyone from feeling used. It reminds you that this person likes you for more than just doing it, which is one of the wonderful parts about FWB situations. Hit that shit, but don’t forget to pay your respects.


Rule #4

Do not get judgey and have expectations (for your FWB or for yourself).

This is a vague rule that can mean a number of things to a number of people, but let me start with an example. If you have a FWB who calls you at the last minute for sex, don’t freak out about the fact that you haven’t shaved your legs. Okay, this is obviously rooted in a real life situation, otherwise I wouldn’t give such a specific example, but there’s a guy I have a nice FWB situation with. I remember we once on a whim decided we wanted to have sex, so I went to his place. I hadn’t shaved in days, because I was single and totally not planning on getting any. He didn’t mention it. We had really good sex. Why should I care if my legs weren’t shaved? Now, let’s say this guy is really super duper into shaved legs, but he really isn’t in a position to say much of anything, and here’s my point exactly – he shouldn’t.

Replace shaving legs for any number of hygienic (within reason, folks) or emotional pleasantries we expect from dating. Part of the appeal of FWBs is the convenience. Once you start expecting certain things like that, then you’re sucking all of the fun out of it.

If you want to shave your legs or buy him a birthday present or any number of things, fine. But if that’s not something you’d normally do, then don’t. If you do it, don’t expect anything like that in return if it’s not something they’d ordinarily do. If you expect these things or do these things, it’s edging into relationship-land, and that’s when people get uncomfortable and weird.

Rule #5

Communicate a lot, and don’t be freaked out about it.

Psh, I know, right? It seems so obvious. But we don’t do it! Or when we do it, we wait until it’s totally boiling over, and it seems like we’re having a psychotic meltdown! Or is that just me?

Here’s the thing. It’s hard to tell how much communication is an okay amount of communication. You don’t want to be overbearing like a partner would be, but you don’t want to leave your communication to just booty calls and sexts. Plus, I mean, there is a level of intimacy that does not exist in casual sex and also exists in a friendship. And you can text your friend to tell them about that really cool awesome thing you saw, right, so why not your FWB?

Believe it or not, seeing this does not mean someone is falling madly in love with you. Anyway, you have bigger things to worry about like buying a new phone, for starters.

You both should talk about how much communication is okay. Communicating about communicating seems redundant, but it’ll save you some grief. I’m a frequent texter to everyone – and if I’m seeing you regularly (that includes boning), you’re going to be on my mind more often, and I’ll have more to say to you. If we both agree like adults that we want this type of relationship, my text to tell you about the cinnamon bun I had this morning should not send you running for the hills. If it does, you do not need to be in a FWB situation. You are not emotionally stable enough for that kind of intimacy, and that’s okay. Just be honest about it.

But honestly, if y’alls’ genitals touch, I think you only owe it to each other to hear from one another occasionally. And if you’re really a friend, you really won’t mind it. If you mind it too much, reassess the FWB situation and possibly even the friendship. You also have to trust that the other person will honor your arrangement. That means you have to trust that other person to not develop strong feelings without talking to you about it first. And how will they talk to you about that sort of thing when you’re being such a dodgy motherfucker about phone calls and texts about stupid shit like what he thought of the latest How I Met Your Mother episode? Good communication means you have to make yourself available and open to being communicated to.

So these are my die-hard rules. I have to say, following these rules does not guarantee anything. Friendships are precarious things as is, so to throw sex into the mix is playing with fire. But fire does some pretty cool stuff like lighting fireworks, or powering a jet engine, or making cheeseburgers. You might get burned, but you might end up having a delicious meal to look back on.

By awkwardette

Michelle M. aka awkwardette is a multi-disciplinarian. She moonlights as an activist while earning her big bucks making the internet easier to use. She also writes about pop music on and aspires to be Amelia Fletcher when she grows up. She prefers listening to The Jesus and Mary Chain when doin' it.

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