How to Have a “Friends With Benefits” Conversation That Doesn’t Blow Up

There is a particular kind of confidence required to look at a perfectly good friendship and think: You know what this is missing? Sex.It can sound easy in theory. You already like each other. You trust each other. And you know way too much to ever want to actually want to be in a relationship with them. So what’s the harm in adding a little making out?Unfortunately, humans are not particularly gifted at keeping sex in neat little emotional boxes.That’s not to say it’s impossible. A friends-with-benefits (FWB) situation can totally work, but only if both people are genuinely on the same page about what it is, what it isn't, and what happens when somebody's feelings inevitably get a little more complicated. “Clear and straightforward boundaries are the foundation for a successful FWB relationship,” sex and relationship therapist Dr. Mindy DeSeta tells Cosmopolitan.The trick, then, isn't figuring out how to make an FWB conversation not awkward. You're talking to your friend about having sex with them. Some awkwardness is inevitable. The real goal is to make it clear enough that nobody has to decode what you meant three weeks later.Before you start drafting your “so… hypothetically…” text, do a little self-interrogation. FWB tends to work best when both people want sex and companionship without the expectations of a committed romantic relationship. Psychologist Dr. Brittany Woolford says the arrangement is most successful when two people are genuinely friends, trust each other, are attracted to one another, and have goals or values that make a long-term relationship unlikely to work. In other words: you’d be great in bed but awful buying one together.Woolford notes that people with anxious attachment styles can sometimes enter an FWB arrangement hoping (consciously or otherwise) that it will eventually turn romantic. People with avoidant attachment styles, meanwhile, may be drawn to the closeness of an FWB relationship because it offers intimacy without the perceived risk of commitment. Neither makes someone incapable of casual sex. But if your internal monologue is already “Maybe if I’m chill enough, they’ll realize I’m the one,” you're probably not negotiating with a friend about an FWB arrangement, but rather with yourself.DeSeta suggests asking whether you're genuinely comfortable being single and whether you'd be able to handle the arrangement ending at any moment. If the answer is no, that's useful information.Friends-With-Benefits vs. Hook-Ups vs. SituationshipsNow, it’s important to realize that FWB is a very clearly defined type of arrangement: it is not a hookup or a situationship. A hookup is generally a one-off or occasional sexual encounter. An FWB relationship is different because there is an existing friendship underneath the sex, and that friendship continues alongside it.“Friends have a history,” DeSeta says. That history is precisely what makes an FWB relationship different—and potentially more complicated—than sleeping with a stranger.Woolford similarly distinguishes FWB from a situationship, where romantic feelings and uncertainty tend to exist without a clear conversation about what the relationship actually is. With FWB, the entire point is that both people have had the conversation and agreed on the arrangement.So if you've been sleeping together for six months, texting all day, getting jealous when the other person goes on dates, and insisting you're “not labeling anything,” congratulations: you may have wandered out of FWB territory.What to Consider Before Bringing Up FWBThe obvious question is whether you're attracted to each other and whether you trust them. But Woolford suggests looking at the wider social ecosystem, too. Is this person your coworker? A member of your closest friend group? Someone your best friend used to date? Someone you're likely to see every Saturday for the foreseeable future?An FWB arrangement doesn't happen in a vacuum. If things go sideways, the fallout may not be limited to two people and an uncomfortable goodbye.And trust matters for more than keeping your secrets. “Even though there's less vulnerability than in a romantic relationship, there's still a level of intimacy and vulnerability that happens, and you want to make sure you can trust this person with those parts of yourself,” Woolford says.This is where the “friend” part is really important: just because you're not dating doesn't mean you should lower your standards for how someone treats you.Now, to the ConversationOK. You’ve done your due diligence, explored all the worst-case scenarios, and have still decided to push through. So if you have someone you think checks all your not-boyfriend material boxes, how do you ask them to be FWB?DeSeta says you can test the waters if you're nervous, but ultimately, conversation is key. Her advice: “Be bold, be confident, and state exactly what you are looking for.” This means being specific enough that they don't have to guess what you're asking.Remember that you’re not really trying to convince your friend to start sleeping with you—you want to find out whether you want the same thing.Something along the lines of: “I’ve been thinking about this, and I’m attracted to you. I’m not looking for a relationship right now, but I’d be interested in something casual if you are. And if you’re not, genuinely no pressure.”Notice the last part. DeSeta recommends giving the other person an easy out and explicitly making it clear that it's okay if they don't want the same thing.Remember that you’re not really trying to convince your friend to start sleeping with you—you want to find out whether you want the same thing.And the only way to do that is to have some real, adult conversation. First, talk about sexual health. Woolford says people sometimes treat questions about sexual health as accusations when they should be treated as basic information. “This is a vital conversation for your health and can make other conversations about sexual preferences easier,” she says.Ask when they were last tested for STIs, whether either of you is sleeping with other people, and what protection you'll use. If either person is seeing other people, be specific about what that means for testing and safer sex.Then talk about the less obvious stuff, like how often you’d want to see each other, whether either of you is dating or looking for a relationship, how the friendship could be affected. Also, talk about boundaries: will cuddles, sleepovers, and other affectionate behavior be on the table? And of course: what happens if one of you catches feelings?The biggest FWB myth is that having rules means nobody will ever develop feelings. People don’t operate like contractual agreements. Feelings can happen even when everyone enters the arrangement with the best intentions.Both experts agree that developing romantic feelings is one of the biggest threats to an FWB arrangement. DeSeta says that once one person starts emotionally liking the other, the dynamic tends to become complicated. Woolford points to the resentment and anxiety that can develop when one person wants more than the other.Maybe you agree to pause the sexual relationship if this happens. Maybe you talk about whether dating is something you actually want to explore. Maybe you end things and take some space. These conversations pre-arrangement aren’t meant to really decide the answers in advance, but rather come to the agreement that you’ll both be honest if and when the situation changes.Signs the Situation Is Going SouthTrust me, you’ll know when the situation changes. DeSeta says a major warning sign is when the FWB arrangement starts getting in the way of pursuing an actual romantic relationship, or leaves you too emotionally exhausted to date. Another is simply when the friendship itself starts taking a hit.If this happens, ask yourself: Am I disappointed when they don't text? Am I getting jealous of the people they're dating? Am I secretly hoping they'll change their mind about relationships? Am I avoiding dating other people because this arrangement is taking up all my emotional bandwidth? If so, the “no strings” label may no longer be doing much work.FWB doesn't have to end because someone did something wrong. Sometimes the arrangement simply stops working. DeSeta argues that these relationships tend to work better when they're relatively short-lived, because the longer they continue, the more opportunity there is for feelings to develop or for the arrangement to interfere with finding a romantic partner.And when it's time to stop, you don't need to have a whole dramatic scene about it. You can simply say: “I think this has been fun, but I don't think it's working for me anymore, and I don't want it to affect our friendship.”That might be uncomfortable. Your friend might be disappointed. You might even feel a little ridiculous for having initiated the whole thing in the first place. And there’s always the chance that one of you just doesn’t feel comfortable continuing the friendship. But of course, these are all things you’ve considered before you even started.A successful FWB relationship isn't one that lasts forever. It's one where two people were honest about what they wanted, treated each other well, communicated when those wants changed, and managed to walk away without turning the friendship into collateral damage. Oh, and of course had some really great sex.