Hi Moxie -- I hope you are well - happy holidays! I wanted to ask about something that's been on my mind lately, particularly after your recent post about f-buddies. I'm single far more often than in a relationship, and I'm faced with potential f-buddy situations more than I am actual or potential relationships (sad but true and also - I acknowledge - partly my doing/"fault"). I have a tendency to get attached so for the most part limit casual sex/hooking up to guys I don't really know and thus won't get attached to because I just don't care about them. However, when it comes to people you know better, are attracted to and want to hook up with, how do you reconcile the desire to be physical and spontaneous with the desire to someday be in a relationship and find the right person? Sometimes I don't realize until I'm too far gone that this is someone I might actually want to be in a relationship with, and at that point it's far too late because I've already communicated through my actions that that's precisely what I don't want. Is the moral of the story that you just shouldn't screw around to begin with unless that is ALL you'll ever want from the situation? Are you supposed to wait until the guy asks you out or ask them out/hint towards that because I feel like saying something to him along the lines of you might want more is just too much too soon. Is there a way to be assertive from the get go and get the physical side that you crave? I'd love whatever insight you have into this; I am realistic about the negative prospects when it comes to turning an f-buddy into anything more, but am wondering what you do before things even being, really. Thanks for any help/advice you might have! Take care, Katie (27 and in Chicago if you want to use it in your column :)) You answered your own question. Is the moral of the story that you just shouldn't screw around to begin with unless that is ALL you'll ever want from the situation? Yes. That's the moral of the story. For starters, the guy isn't going to do the right thing and cut things off or not take things to f-buddy territory for you. He might eventually cut things off because he doesn't want to feel the guilt or have his life inconvenienced. But, most times, he's not going to weigh the pros and cons of having casual sex with a woman. He's just going to do it. So he isn't going to be responsible for you or your feelings. And really, it's not his job. That's your job. If the f-buddy situation presents itself, and it's with a guy that you could see yourself falling for, then there's nothing wrong with saying, upfront, that you don't think sex would be a good idea because you know yourself well enough to know you'll get attached. You don't have to profess feelings. You can tell him that you like him enough that you think the lines would get blurred and that the few hours of rolling around in the sheets might not be worth how you'd feel after. In fact, men WANT us to be more responsible and communicative in these situations. Most guys are good guys. When they get horny, they're just not thinking about what it right or wrong. We kind of HAVE to be the clear headed ones in those situations. I have said, from the day this blog started, that anybody should have the freedom to do whatever they choose. If they want to have casual sex, fine. If they want a relationship, fine. Just be honest with yourself about what you want and who you are. And realize that allowing yourself to be sidetracked too often when you know in your heart that you want a relationship will only serve to keep that goal further out of reach. This is a section from a chapter sample ( read the whole chapter sample here ) from my book proposal that I think kind of fits here. The title of the chapter is No Myth, based on the Michael Penn song. The tune, told from a man's perspective, is about a woman who sort of flits through life, dating and sleeping with man after man, never settling down with any of them for whatever reason. What if I were Romeo in black jeans?/What if I was Heathcliff? It’s no myth/Maybe she’s just looking for someone to dance with. Maybe she's just looking for someone to dance with. Translation: Maybe the reason why she can never find what she wants is because she doesn't know what she wants.Or does, but is afraid of it. I guess what it all comes down to is this. In order to find someone worthy of you, that fits, you have to know what you really want. Until you have a very specific idea of what kind of relationship you seek and determine what it is you bring to the table – be it in good qualities or bad – and own them, you will continue to find men that aren’t quite right. This means not allowing yourself to get side tracked or deluding yourself. We all like a little fun here and there. We all love the idea of having options. But continue to rely on this idea of endless supply of possibilities and you will find yourself, like the cheese, standing alone. Now, maybe that’s okay by you. (Though , if it were, I don’t think you’d have read this far.) Perhaps you are perfectly content with your life as a swinging single. More power to you. But don’t let this fear of looking weak prevent you from being honest with yourself about what it is you truly want. It’s funny. Women will casually and freely announce that they’re just looking to get laid and will go and do so. For some reason, that’s considered empowering. Yet admitting that you’d like to have a partner or that you feel life would be that much better if you had someone to share it with for some reason is frowned upon and makes us look needy or desperate. Don’t buy in to that. Because if you tell yourself that too often and for too long, you’ll start to believe it, and then everybody you attract will bring with them that same kind of fear. The only way to find what you're looking for is to first be honest with yourself about what that is. And then sticking to that game plan. Nobody is saying you can't break loose every so often. But F-Buddies are like pretzels. You can't stop at just one. And pretty soon you'll have a string of lovers in your wake because you've spent so much time hiding behind or settling for that that you won't know what you want anymore. Got a dating related question? Want free advice from Moxie and dozens of other national and international singles? Ask Away. It’s Free! Look for Moxie’s response and feedback from others SUBMIT YOUR DATING ADVICE QUESTIONS HERE: http://moxieinthecity.net/ask-email.php Follow me on Twitter http://twitter.com/Moxieinthecity