Ask Kayy

Dear Kayy,

I have a good friend from high school that I’ve always had mutual feelings for. Whether it was a crush or real feelings or whatever, we always kind of ignored it and never acted on it. That is, until my freshman year of college when we finally succumbed to the inevitable. I was totally fine with what happened, and the next day talked to him like I normally do, but he kind of freaked out and walked away from me. Later I found out he told every single one of our guy friends exactly what happened within hours of the first kiss. He was really upset, supposedly because it “ruined our friendship,” but I think he was embarrassed because . something embarrassing happened to him (as in – he had trouble “rising to the occasion”). Well, regardless of his reasons for being all weirded out, he has refused to speak to me ever since (over eight months later!). I wish I could say I’ve tried to do something besides talk through friends, but I’m too scared he’ll blow up in my face, and I’m not sure the right way to go about it.


A Very Friendly Girl Friend

Dear Very Friendly Girl Friend,

Congratulations on daring to do the unthinkable and terrifying act of . hooking up with a childhood chum! You’ve got some real bravado . and so do the ten million other women and men who have made the same exact mistake (me included).

I wish you had acted earlier. You might think you’re giving him time to calm down, to ease his nerves and nurse his ego, but you’ve probably gotten so distant that you’ll feel a bit foolish addressing it. But if your friendship was as important as you claim it was, read on, and get ready to confront a VAS – Very Awkward Situation.

You said you’ve been interested in each other for a really long time but never acted on it, which is probably for a reason. My guess is your hormones remained stagnant throughout high school because they weren’t serious enough to start a real relationship over, but your friendship wasn’t worth risking over some heavy petting in the back seat of his daddy’s pickup truck. Ding ding ding! Perhaps it should have stayed that way.

College probably let you grow into your sexual selves a bit more, and being away from each other led to a more severe case of curiosity. So next chance you got you decided to go for it because – why the hell not? He’s a boy, you’re a girl, it’s the twenty-first century . yadda yadda.

I’m not going to judge you for making that decision, because as I mentioned before, many people have crossed the thin “F” line of friendship.

But don’t worry, most have gone on to live relatively normal lives, and in the case of most chick flicks, sometimes a marriage proposal even follows. However, this is obviously not your case.

It’s pretty well established by now that you had both thought about this big “Hook Up Event” for a long time. Sometimes when we play the “what if” game too many times or we create and recreate a scenario in our minds over and over, it tends to be unattainable.

You probably pictured warm lighting, silk sheets and multiple orgasms, which are highly unlikely circumstances for a first hookup (if you want to prove me wrong, write me about it, in detail please!). So regardless of how good a hookup is, if you’ve been salivating over it for years, you can’t help but feel disappointed – Awkward Point One.

Awkward Point Two: It quite obviously didn’t go the way you planned. There’s nothing wrong with some good making out and calling it a day, but it seems you had further plans which went kerplunk.

You have to remember that although you may not have really cared about his little man’s lack of excitement, it probably felt like his sexual demise. Men place a lot of (too much) importance on their penises – how it looks, how it gets and stays hard, how it performs – and when it doesn’t live up to his expectations, he can be extremely disheartened and embarrassed even if his partner doesn’t mind. Especially since this was such a hyped-up hookup, he was probably really pissed that he couldn’t follow through.

In fact, whenever he saw you or talked to you soon after, he probably thought of that very moment and got embarrassed all over again.

Awkward Point Three: To make matters worse, you share mutual friends, and he probably imagined you spilling every humiliating detail to your social circle’s notorious gossiper, who laughed while taking notes for her public blog.

So although you were frustrated or hurt that he immediately told your friends about the debacle, the truth is he was probably doing it to cover his own ass and escape later accusations of an exaggerated rumor. I guarantee he wasn’t trying to embarrass you or call you out; he was selfish at worst and just concerned with his own performance and reputation.

There could be many other reasons for his freak-out compared to your cool composure. Maybe he doesn’t hook up as much as you do and it meant more to him or maybe he’d had real feelings for you and realized you didn’t feel the same, or maybe he’s mad at himself for taking advantage of a friend whom he cares about. Maybe he’s just genuinely scared he’ll lose you.

Whatever the reason for his actions, he’s probably more embarrassed or upset than vengeful or angry with you, be sensitive. I’m not saying it’s right, but he’s probably disguised his true feelings with anger or apathy in order to save face.

There’s no excuse for him ignoring you this long, but you’re obviously the more confident one, so what’s the harm in making the first move? It may be awkward at first, and you may never be as close as you were before the Awkward Hookup, but maybe you’ll get there little by little.

Give him a call or IM him. Ask about his family or classes, and tell him what you’ve been up to. Just remain casual and be yourself so he remembers why you were friends in the first place. And then get to the heart of this situation. Maybe start with a joke about your past to break the ice, and then tell him you want everything to be cool between you.

I wouldn’t suggest hashing out the details of the night since he’s probably still sore about it. Do, however, let him know that you’re not upset about that night, but you are hurt by the way he handled it. Allow him to apologize for ignoring you. Things won’t be hunky dory, but it’s a start. Just keep in mind all the things you like about him, hold your breath, and forge on when it gets awkward.

Oh, and if he doesn’t return your calls, keep calling. Don’t be annoying, but do make a visible effort to right what went wrong.

Wow. Maybe I’ll take my own advice.

– Kayy