This is because, well, we’re all human beings, and we have individual tastes, experiences, morals, habits, emotions, perspectives and desires. That said, it should come as no surprise that the world of “friends with benefits” can be fraught with difficulty. That’s not to say it’s not a good idea, or that it’s doomed to fail; the reason it’s become such a popular catchphrase is because, well, duh, everyone’s doing it! So it must be working for them, right?

Wrong. The first thing is to make no assumptions. Lots of people enter into the idea that entering into a “friends with benefits’ situation is the answer to their prayers: no more being lonely/horny/unloved, plus they get to take a friendship to a whole new level. But people may have differing motivations for wanting this kind of tete-a-tete: some may truly just want sex with someone they know and trust, and with whom they feel safer and more comfortable with than a bar hook-up.

But some people may harbor deeper feelings for this friend, and may (consciously or unconsciously) believe that “hooking up” with said friend will naturally lead to a cozy romantic relationship (of the type that “friends with benefits” seekers are supposedly trying to rise above!), and when two opposing sets of expectations collide, whoa! You(or your friend) may not be able to see or admit this right away, but the resulting fallout from such a misunderstanding can be painful and ugly. This dissonance may happen as quickly as the initial conversation, or may take weeks or months to become clear, but when it does, hello! Quicker than you can say “Hey you know, I’ve been wanting to ask you about something,” you suddenly find yourself minus one fuck bud–er, sorry, friend with benefits–and, quite possibly, minus one friend.

Now, if you’re reading this article in the first place, clearly you want to avoid all that. But I wanted to get it out there so you’d consider your motivation. You see, men and women differ in these matters. Yeah, yeah, I know, you don’t expect this silly sexist drivel on sssh.com, but it’s worth noting that men are far more likely to want casual sex with no strings attached, and that women will have some sort of emotional connection to such a relationship. But we’re all capable of being trustworthy adults, and the Number One rule attached to any relationship, of course, is to BE HONEST.

If you are thinking of approaching a male friend to say you want more with your weekly round of beers than, say, a plate of nachos, then you need to first of all be honest with yourself. Consider the implications. First of all, are you ready to sacrifice this friendship? Because it is possible that the very mention of such an arrangement might freak him out, and even once it’s behind you it may continue to affect the nice rapport you already have. It is also possible that, once you have achieved “friends with benefits” status, one of you may want more, and the other may want to keep it casual, and odd as it may sound, this situation leads to the same sort of crying/yelling/processing crap that a traditional break-up does!

For these reasons, friends with benefits situations tend to be more successful with casual acquaintances than with long-time pals. If he is a good friend, one you value and want to hold on to, consider the possibility that maybe what you want is a real romantic relationship with him; I mean, if you’re sexually attracted to him, what has kept you from acting on it before now? Maybe one or both of you was involved with someone else when you met. Maybe now you’ve become so comfortable with each other that the whole process of discovery and newness that, let’s face it, makes love worth pursuing, would not be there for you; you might even feel a bit silly at the thought of sex with someone you’ve been through a lot with already. But the new element you would be adding to your relationship, sex, might be enough to let you see things as exciting and mysterious. Just don’t confuse the new, exciting sexual possibilities with romance, and you just might be able to pull this off.

Do consider the possibility that maybe the attraction isn’t mutual. Nothing is worse than rejection, but between two friends such an admission can be devastating and make for much awkwardness. But being the savvy, self-confident gal you are, you probably already have some idea if there is chemistry lurking. If you tend to have somewhat flirtatious conversations, if you are able to have open conversations about sex and relationships, and if he tends to ask your advice about previous girlfriends, well, chances are there might be <i>something</i> there.

So, you’ve decided to make your move. How to go about it?

There are some potentially-promising situations that lend themselves to a foray into friends-with-benefits land. But before you actually bring up the topic, lay the groundwork. Drop some hints. For example, you’re at the mall and a guy whose physique/hair/sense of style resembles his walks by. Be sure to comment that you like the way that guy looks and then describe why; feel free to add the phrase “like yours” to help him get the hint that you find him appealing as a guy, as well as a friend. You may also find it helpful to observe his reaction when you say things like “You know sometimes I think relationships are just too much work; why can’t people just have some friendly sex once in a while instead of all this heavy involvement and moving in together?” Maybe he will agree. See where the conversation goes.

Be physical with him. See if he notices if your hand touches his when you hand him a drink or bag of chips. Rub his shoulders if he’s working hard at his desk. This need not be construed as flirtation, but it certainly could be. Check for his response: if he starts acting awkward or ignores it, you might want to reconsider your course of action. If he seems comfortable or starts being more physical with you, there may be some good possibilities brewing.

It may be that when the times comes for adding benefits to your friendship, it may catch you both by surprise. Maybe the hints you start dropping will have an immediate effect. But if you’d like to plan for an auspicious moment, choose a comfortable atmosphere. Your favorite pub or diner, the local park, maybe your apartment. Be upfront but don’t come on too strong. Say you like him, you value your friendship and would not want anything to change. But say you also think he is attractive and you have wondered what it might be like to add a sexual component to your friendship.

There are many possible responses. He may mumble in an embarrassed way, leave immediately and refuse to answer your calls for weeks. He may grab you and start kissing you passionately. But most likely it will be somewhere in between. For example: He may like the idea but worry about “rules” or boundaries. No sweat; let him know you’d really appreciate laying out some ground rules before you enter into anything. Or maybe he will say he’s attracted to you but he’s worried it may affect your friendship. If this happens, be reassuring. Say your friendship is more important than anything else, tell him you are perfectly willing to keep things as they are, say that you hope this hasn’t been awkward for him, and then ask him to pass the pretzels. That simple. If he decides he does want to pursue this later, he’ll know the potential interest is there on your end.

Let’s say he is eager to pursue this possibility. It’s very important to communicate about what’s appropriate and what will work for you. Is a 3 am booty call acceptable, or not? If you’re going to be at the same party, will you have a signal to let each other know you’d be up for going home together, without letting your other friends in on it? (That is another issue to be aware of, whether you will want your mutual pals to know what is up. My advice: it’s none of their business). Is staying the night encouraged, or do you both want your own space in the morning? If your friendship is already based on mutual respect, these conversations should make things easier. But be careful: sometimes all this negotiation can feel like the “work” of a real relationship, and then, well, you may need to redefine where you’re both at.

Friends with benefits can be a very freeing, wonderful way to have the best of both worlds: sex, and companionship–if not necessarily at the same time.