We’ve all been there. You have a friend – either for many years or for a shorter period of your life. You’re totally fine being platonic. You hang out. One or both of you dates other people. But the timing was never right, or you just didn’t entertain it for one reason or another.

And then one day something just…shifts. Suddenly your view of them changes, and you realize hooking up with said friend could be a serious possibility. Do you succumb to the sexual tension? Or do you hold out for the sake of the friendship?

Having gone down that road before (OK fine, more than once) allow me to be your cautionary tale, boys. Women and men view friendship, not to be confused with a Friends With Benefits setup – another, more casual arrangement entirely – in a totally different light. So, it’s only fair that, prior to taking the plunge, you consider several factors in your decision.

Call it a Should-I-or-Shouldn’t-I Checklist of sorts. Yes, when it comes to hooking up with friends, you may be getting way more than you bargained for in the end. Here’s what you need to weigh out first:

Why Do You Want To Cross That Line? It’s important to figure out your motivation for hooking up before clothes are being discarded onto the floor. Is it just good, old-fashioned sexual attraction? Have you always wondered what it would be like to roll around with your previously platonic pal? Or are you looking for something more substantial? Being on different pages here is what will set the tone for how this whole scenario plays out. If you think it’s just casual but she has feelings behind it (or vice versa), you’re headed down a dangerous path. That’s why it’s so important before you do anything to…

Define Your Expectations. Where are each of you at in your lives? If you’re both looking for something with serious potential, then you’re in line to give this thing a real shot at working out. The best relationships start out as friendships, after all. Or if you’re both just looking to break the sexual tension, then you may also skate by unscathed here, and have fun doing it. But if one of you would entertain the option of actually making room in your life for the other, but it’s not reciprocated, then you’ve just booked a one-way ticked to Disappointment City – Population: you.

Examine Their Track Record. Taking into consideration how your potential hook up treats (or avoids) their past hook ups could be very telling. If they have a tendency to pull a disappearing act, don’t think it won’t happen to you. This may be the biggest rift in the difference between how men and women view hook ups between friends. We think that, because you know us and (theoretically) respect us, you’d never relegate us to the same fate as just any old flame. Certainly you wouldn’t categorize us with the other hook up women in your phone…would you?

Right. Just because there’s a back story, doesn’t always mean that guys will make that distinction (sucks for us, I know). But women do it too, so if your gut says there’s a good chance you’ll get phased out, listen to it. History has a tendency to repeat itself.

Weigh The Consequences. If the friendship you have is so great that you’re not willing to gamble losing it, then, simply put, don’t. Because that’s exactly what hooking up would be – a gamble. And that’s a pretty big hand to play. You can’t predict or control the outcome entirely, so be prepared that you just may lose that person entirely from your life.

Sure, some people have hooked up and then gone back to being friends seamlessly (Dave Matthews Band “Say Goodbye,” anyone?) Even I’ve had instances where the friendship wasn’t disrupted post-tangling. But more often than not, the quickest way to ruin a friendship is through sex (or even less). It seems like a good idea at the time, but it’ll have to be one hell of a hook up to trump the gaping hole that might follow.

But not matter what, make sure you Acknowledge It Afterward. If you don’t have the conversation about where each of you is at beforehand, then this is the only way to make sure you’re both on the same page post-incident. Or salvage it. Or just damage control, whatever. If I could point to the single most important point in this whole article, it would be this one – make sure to talk about it afterward.

It doesn’t have to be some weird, drawn-out sit down (we know you guys hate that anyway), but if you respect the person you hooked up with, you will find the time to talk it out. No one can blame you for feeling the way you feel, but they can blame you for not clarifying it in a timely manner. This could be the difference between going back to normal or deleting someone from your phone. And if you have years invested in that friend, it’d be a damn shame to throw it away over something so avoidable.

That’s the gist of it, lovebirds. I’d love to be able to say that hooking up gets easier post-college, but it doesn’t. In fact, once you hit your late twenties and beyond, it gets really, really complicated. Somehow the stakes just seem higher. It’s like people feel like the sand is falling through the hourglass, and any wasting of their time is not only inconsiderate, it’s cruel.

At the same time, this is when people are more likely to turn to their friends for dating or hook ups, because they’re familiar, you trust them, and let’s face it – there might be precious few of you left who aren’t wearing wedding rings. That’s another unfortunate sidebar to this conversation: You know you’re getting old when the list of people in your phone who you’d normally hook up with dwindles, because they’re someone’s fiancee now or have a kid on the way. Whoa.

I suppose you could use that as an excuse to justify hooking up with your friends this late in life though – they’re all going to end up married soon enough, where your friendships will take a backseat anyway. So you may as well go the anticlimactic route, nothing to lose!

Kidding. Whatever you choose, remember that you should treat your friends differently than other people you have romantic dalliances with, because it’s the right thing to do. Show them the respect they deserve, weigh the possible outcomes, and arrive at your choice more deliberately than you would with just any old stranger.

If things work out? Great! But if they don’t? Hopefully you can maintain some sort of relationship afterward. Hook ups come and go, but friendships – if they’re worth it – last a lifetime.THAT’S WHAT SHE SAID

Facebook Twitter