So, I have a bit of a bad habit of hooking up with my best guy friends. (I know I’m not alone on this one…) Bestie hook-ups are just one of those things that always seem to happen between friends of the opposite sex – no matter how sure you are that it never will.
Over the years I have hooked up with 3 of my best guy friends with a variety of results. With Mr. Tall, it was pretty much a disaster. We don’t speak of it, and frankly, these days, we just don’t speak. With Ad Dude, it was confusing at first, then a disaster, and then eventually, just fine. And with My Bestie, it has been actually quite perfect. No drama, no awkwardness and lots of fun.
Since My. Bestie is coming to town this week (yaaay!) it got me thinking about what one should consider before hooking up with their best friend. Ladies, if you want to avoid awkwardness here are a few things to consider before you cross that line.
1. Why does he want to cross the line? If the answer is: he’s super hammered and you just happen to be there — don’t do it. You are risking your friendship, and besides, it probably won’t be a good hookup. If you think there is something more to it and that perhaps he’s been wanting to “cross the line” for sometime but wasn’t sure how, then perhaps it is something worth considering.
2. How drunk are you? You’ve already assessed his level of drunkness (see above) but make sure you check yourself. If you are blasted out of your mind, he’s going to feel all awkward about “taking advantage” of his best girl friend and think that you probably didn’t mean to hook up with him. His insecurity will breed awkwardness, I promise.
3. Is he in a good place in his life? As his best friend, you’ll certainly know if he is in the middle of some existential life crisis. If he is in between jobs, questioning the meaning of life, and just generally down in the dumps, this is not an opportune time to test out these waters.
4. How does he act about other girls he hooks up with? Before Mr. Tall and I crossed the line, I was privy to many-a-convo about the silly girls he hooked up with. Not to make him sound like an ass, but these conversations should have been a clue to me that he has no problem with hooking up with a girl he doesn’t intend to date. Of course, like most girls, I convinced myself it would be different with me, because we were best friends and he had too much respect for me to treat me like that. And like most girls, I was wrong.
5. How close are you? This is a double edge sword. On one hand if you are super close you can call him on his bullshit if he starts to act weird. On the other hand, if you are super close, you have more to lose if your friendship goes down the tubes.
6. How long have you been friends? My Bestie and I have been friends for 10 years and we waited 8 years before crossing that line. On the other hand, with both Mr. Tall and Ad Dude, we were only friends for a few months when something happened. This was a result of the fact that we were spending a LOT of time together as friends. In fact, I even lived with Mr. Tall and I worked with both of them (sorry co-workers who read this blog for that over-share). At the time, it seemed natural that these friendships progressed so quickly but in hindsight, I wish I had waited to explore that territory. I’ve since realized that the longer you have been friends, the better foundation you have, and the better you can handle the inevitable awkwardness of the hook-up situation.
7. Have you talked about this as a possibility before? While My Bestie and I waited 8 years to cross the line, we’d been talking about doing it for at least 5 years prior. By talking about it for so long beforehand, it made it clear to both of us that this wasn’t something that was just accidentally happening, which is probably why it was never weird or different. On the other hand, with Mr. Tall we also talked about it before hand but in the context of how it would never happen. You see, Mr. Not Quite Right was uber-jealous of Mr. Tall, so much so, that Mr. Tall was actually the subject of our final fight. I, of course, told Mr. Tall this, and he protested that this was ridiculous because “we were just friends.” A whole week later I woke up at his house. And judging by the aftermath of this hook-up, his denial that he had a crush on me should have been a clue I paid a bit more attention to.
8. What do you want out of it? Could you see yourself dating your best friend? If so, you better be darn sure he is on the same page before anything happens. If you want to date him and he doesn’t want to date you, that will hurt like hell. Then you get to deal with being rejected and losing a bestie in one swoop. Good times
9. Where does he live? This may seem silly, but part of the reason I think things worked out so well with me and My Bestie is that he lives in Colorado – much too far for me to actually try and date him. This way, we can both pretend that we’d be dating if we lived closer (even though I’m pretty sure we wouldn’t) and no ones’ feelings get hurt. The same was true for Ad Dude. Things were pretty awkward between us for a long while – right up until he decided to move back to Minnesota. From that point on everything was fine, because there was no pressure or wondering, “why aren’t we dating?”
At the end of the day, the bestie hook-up is a complicated but common situation — approach it cautiously and with care. When it works out, it is perfect. But when it sucks, it is downright disastrous. Most importantly, keep in mind that if the bestie hook-up does result in you losing a friend, well then he wasn’t really a good friend anyway.