Does Friends With Benefits Ruin Everything?

I feel like in many ways you are my unofficial advice provider, and do I desperately need it now.
The short version is, I’m in love with my best friend. We started out just as friends and things quickly escalated for me into a feeling more deep and profound then I have ever known. The catch is that I don’t necessarily want to be in a relationship with him, our friendship is fantastic and I fear that anything more than that would ruin us (as well as the fact that he is moving away shortly).
A few months back I told him how I felt, not in hopes of hearing it in return because I knew I wouldn’t, but more as a protective shield for me to not be privy to the more private aspects of his life, it cuts like a knife to hear him talk about other girls. My admission to him was treated with a lot of respect and really benefitted our friendship. He admitted to having those feelings for me too, but that he could not act on them because he does not want to ruin our friendship and that he wants me in his life for the long haul and that it isn’t fair of him to do that to me. I am totally okay with this.
He proposed to me that we become friends with benefits, knowing full well how I feel for him and saying that for us it would be a happy middle ground. At first I was really offended, that he would disregard my feelings like that. Then I realized that the expiration date on our friendship was looming, and that being with him really is the best part of my life right now, and that I do want that with him, in any regard. I have literally NO experience in this realm of sex and friendship, and we both agreed that a healthy amount of alcohol would have to play into our first time together because we know each other so well and are each others best friends.
Surprisingly, the first time was in the haze of a hangover, but neither of us were drunk enough to ignore the awkwardness and weirdness that was occurring. After this we agreed it wouldn’t happen again, and here is my problem. I am panicking, because I fear that he will find someone else to sleep with, who will take up the very precious limited time I have with him person to person. I know it was terribly awkward and that the situation is in a lot of ways degrading to me, but I really feel like I need a second chance in this department, to help us ‘be together’ without screwing everything up.
I don’t have any idea how to approach this subject, am I shooting myself in the foot by wanting it from him? Would I really regret this a month from now? I feel as if all the things you hear about love and caring for someone else isn’t in the cards for me, if this is what love feels like, a big mess with more potential to fail than to succeed. Is friends with benefits ever really a benefit or does it ruin everything?

While love can sometimes feel like “a big mess with more potential to fail than to succeed”, I don’t think TRUE love does. I think falling in love with someone who is wildly inappropriate feels like this. I think unrequited love feels like this. I think relationships that only make one half of the couple happy feels like this. I don’t think The Real Deal feels like that at all. Maybe that will give you a little hope!

Now, to answer your question. In my experience, “friends with benefits” tends to end up being more about the “benefits” than the friendship part. It can be tricky to go back to being buddies after you’ve seen someone’s O-face!

I have been in situations where the friendship turned into something more, & then I decided that it was a Really Really Bad Idea, & turned it back around to friendship. I believe the conversation went something like, “Hey, yeah, about last night — let’s never do that again.” I think I was lucky in that the guy I said this to had a pretty bulletproof ego; well, either that or he faked it well, & our friendship managed to continue. This is not to say it was entirely without awkwardness — it wasn’t, & even these days, sometimes when we hang out, you can feel it in the room. But I think this is a best case scenario. We went there, decided it was a bad call, & redirected things, & we’re still friends.

I think I’ve been lucky, really. These situations do not always go so seamlessly.

To address your specific situation, I think the real source of pain springs from the fact that you’re trying to help the two of you “be together” when only one of you is interested in such a thing.

(I don’t mean to be harsh & I hate to quote this book because it’s such a cliche, but unfortunately I’m going to have to.)

If you tell him you love him & he says he doesn’t want to ruin your friendship — HE’S JUST NOT THAT INTO YOU.

I’m not going to dance around the topic because I think sometimes women can be guilty of telling one another lies in order to preserve one another’s feelings. I don’t want to hurt or offend you, but I think in the long run, telling you, “Oh well, maybe you can make it work, maybe he’s just confused about how he feels, blah blah blah” is more harmful than telling you the truth.

If he really liked you, he’d say, “Damn the friendship, let’s DO this!” But he didn’t. He offered sex instead. Most men (& plenty of women) will. I know this is kind of crass & definitely not what you want to hear, but it’s true.

This is not to say that he took advantage of you, or that he doesn’t care about you. I’m sure that’s not the case. Maybe I’m reading too much into this, but it was your first time, yeah? If so, the great thing about this situation is that it was with someone you care about, & someone who cares about you. Maybe he doesn’t feel for you romantically, but you are important to him & you were with someone you trust. Those are all wonderful things.

You’re friends, & he clearly values you. I do, however, think he behaved selfishly & didn’t really think it through.

In my opinion, you’ve made the classic mistake of caving to the pressure — the meager offerings he’s made — because you’re so desperate to get close to him. I’ve written about this before, & of course only because it is my own experience, but about how a lot of us think that having sex with someone is the best way to get close to them. You meet someone who you think is amazing, & the only way you know to connect with them is to get into bed. The truth is, there are many better ways to get intimate with someone & none (or, very few!) of them involve taking your clothes off. I know my best friends far better than their one-night stands ever will. Knowing what someone looks like without their clothes on doesn’t mean anything at all. Knowing who they really ARE, however, does.

The real crux of the matter is that he is behaving selfishly, because he knows you want more, but he isn’t willing to give you that. He wants to have his cake & eat it too. Let’s call him Mister Cake. He wants to have sex without strings, & that’s FINE, but only if that’s what you want, too! & it ain’t!

You want to be in a relationship with someone who doesn’t want to be in one. There is no saving this situation. You are in different places. You cannot spin it or change it. Please don’t think, Oh, but if only I was more _____, or Oh, if only I did _______, because this is a sure route to disappointment & confusion. You need to let him go. He’s not into it, & that’s okay. It HURTS like mad, but it won’t kill you. Life goes on.

It’s tough when things don’t work out the way you want them to. As hard as it can be, try not to take it personally. I know that sometimes when things don’t work out with someone, you can get an attack of insanity. Am I somehow deficient?! What did I do wrong? What could I have done better? You can think that way for a little while, but not too long, because it will surely drive you bats.

This is your new mantra:

It’s not me, it’s you.

Repeat it to yourself day in, day out. Live it, breathe it, dream it. Write it on your bulletin board. This is (truly) one of the secrets of life, & definitely one of the keys to not taking things in life personally. People can only EVER operate from their own experience, which means that everything they do springs from something within them. You could be absolutely pitch-perfect, but something tweaks inside them & they spin out. You can’t take their stuff on, it will make you nuts. Like Russell Simmons says, do you.

You said that he’s about to move away. GREAT. This is excellent news. It will make the temptation to obsessively stalk him, drive past his house, just happen to show up at his workplace, etc., much less alluring!

Help organise his going-away party. Blow up balloons, rent a bubble machine, drink scotch from the other side of the room & watch him say goodbye to his friends. Wear lots of eyeliner & send him off with a kiss on the cheek. It will be marvellous & poetic, you can write about it later.

Continue with your life. Among the detritus of modern life, with its shopping lists & computer viruses & troublesome neighbours, wonderful things will happen. One day, you’ll see a boy out of the corner of your eye, & you’ll secretly love the way he ties his scarf. You’ll meet his dog & you’ll like the way he opens doors for you. He’ll really listen to the things you say & you’ll watch some fireworks together & all of a sudden you’ll be transported into another dimension. Mister Cake will disappear into the vortex of your mind, & sometimes you’ll think of him, but just faintly, & with a wry smile, & when he comes back to town in a few years & wants to catch up over coffee, you’ll think, I’m so glad I didn’t waste more time on you.