Welcome to Step off the Ledge, our weekly advice column. My name is Lauren, and I’m here to help — with a heavy dose of cynicism and a smidge of sarcasm.
Dear Lauren: I enjoy sexual play with others. The problem being? Asking someone for it is awkward. Let me elaborate. I’m a male and I’m afraid if I ask my female friends to mess around sexually they’ll just see me as another guy who only cares about is sex. Any advice on how to ask without making it awkward?
Not really. It’s sort of an awkward question – though I applaud you for thinking to ask instead of just going for it after shotgunning one too many at a party.
So you want to try friends with benefits, potentially with multiple friends. You’ve established relationships with these women, which entails a certain amount of trust. This is true for all relationships, not just those of different gender identities. Asking someone to suspend that trust to add an element of vulnerability to the relationship could change the way they see you as a friend, whether they turn down your offer or not.
I never saw “No Strings Attached” or “Friends With Benefits,” but here’s what I would do:
Do some reconnaissance work to figure out a friend’s general feelings on sexual friendships sans romance. You don’t have to randomly blurt out, “Hey, would you ever screw, say, me?” But if you find yourself talking about, say, current events, you could say something like, “Ugh, if I have to read one more article about college ‘hook-up culture’ I’m going to walk into traffic. Is it really that big a deal for people to have one-night stands, or friends with benefits?”
Your friend might say something to the effect of, “Yes, it’s totally a big deal! I’d only want to be sexually involved with someone if we were exclusive.” Or they could say, “You’re right. Who cares if you hook-up with whomever you want, whenever you want?”
In the course of regular conversation, you’ve discovered how your friend theoretically feels about a friends with benefits scenario. Now you have to add yourself to the equation.
The best way to make a conversation awkward is to start it by saying, “I know this is awkward, but …” Instead, clearly phrase what you want: “I wanted to ask your opinion on something. I’m not ready to be someone’s boyfriend, but I do like [sex/making out/kink/insert sexual activity here]. But I’d feel more comfortable being with a friend then with someone I met at a party or online. Would you ever want to hook-up? Yes, like that stupid f*$king Justin Timberlake movie. Only not stupid. What do you think?”
And, if they feel comfortable communicating with you, they’ll tell you what they think. Or jump you. If they laugh it off or evade the question, this probably isn’t the person to start messing around with. FWB only works if both people know what they’re getting into. You know what it’s like talking to a new person – where you read too much into every text and have a freak out session when they don’t call you the day after, or within three days? Now you have that, plus one of the people you could vent to about your confusing relationships is IN the confusing relationship. Totally not worth it.
Depending on your specific relationship, your lady friends might, in nicer terms, tell you that it’s not them, it’s you.
“I see you more as a brother.” “You’re not really my type.” “I’m not looking for that kind of relationship right now. Not that there’s anything wrong with you wanting to!” It’s a blow to the ego, but totally their right to refuse.
FWB might work better with a newer friend – someone you haven’t really developed a history with. And as cynical as it sounds, if things got too awkward, would you rather lose a fledgling friendship, or one of many years?
And it might be kind of weird for you both after you propose FWB. It’s better to take responsibility early then letting feelings and questions fester in both your minds. Make sure your friend knows that they can always count on you as a friend, that you are in no way upset about their decision, and that their friendship is your first priority, not getting laid.
Unless their friendship isn’t your first priority, and your goal in becoming friends with women is eventually sharing their beds. In which case you’re “that guy,” and you should click here to learn how to not be such a sack of shit.