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

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After spending some time on the other coast, I’ve realized that the dating scene – at least on surface level – looks different depending on what city you call home. New York and LA might as well exist on different planets.

But, there are two fundamental truths that ring true in both places: people (for the most part) just want to find someone to call their own, and that person will almost certainly not be found at a bar. This idea is hammered home this week by Matt from LA’s tale of dating gone wrong. I hope you enjoy it.

The Swap: “I don’t know if this story can technically be considered an ‘online dating’ horror story exactly, but since it started out that way I think it fits. I met this girl online and after emailing/talking on the phone for a week we decided to meet. She’d seemed cool right up until that point, but then when we finally had a conversation face to face it was just…crickets. She was cute but not terribly high energy and we were struggling to think of things to say. So, we parted ways early and my friends met me out to salvage the rest of the night.

Turns out I met another girl at the same bar later that night who seemed pretty cool (OK hot) and she was with some friends, but she promptly ditched them and we started taking shots. Second girl seemed normal enough, she told me she was in grad school, was 23 and had moved out here a year ago. We started talking about how bad my first date had gone and she and I hit it off comparing bad online dating experiences with each other. I guess we both got pretty drunk (at one point she disappeared for a half hour), but by the end of the night she and I left together and went back to my place.

We hooked up for a while back at my apartment and then she excused herself to use the bathroom. When she didn’t return right away I went to check on her and found her nodding off on the toilet (not hot, by the way). Even though she was embarrassed she came back into my room. Nothing kills the mood like seeing a girl with her pants around her ankles, things were pretty much done after that.

I must’ve passed out not long after, because when I woke up in the morning she was already gone. I guess at some point she must’ve migrated out of my bed to the family room, but I slept through it. I didn’t realize it until I headed to the kitchen and saw a huge wet stain on the cushions where the girl had obviously peed on my couch. Yup. What girl does that?! I also found out later that one of my friends made out with her at the bar accidentally before he realized that she’d been talking to me. She was coming out of the ladies room when it happened. Pretty sure that qualifies as a horror story in my book.”

Ohhhhh Matt… Where do I begin? Yes, that qualifies, you’re right. But here are my observations, in no particular order: 1) The girl you met online wasn’t terribly “high energy?” Totally fine if there’s no chemistry, but what were you expecting, cartwheels? 2) What 23-year-old has online dating stories to compare? That’s ridiculous, like those women on The Bachelor who say they’re looking for a husband straight out of college. Be young! Worry about the other stuff later.

Thirdly, her passing out in your bathroom should’ve been her cue to leave, not sure how one recovers from that frankly. 4) Destruction of property, albeit gross and alcohol-driven, usually warrants a stealthy escape, that’s hardly shocking – even I’d support it 5) Your friend “accidentally” made out with her? Sounds suspect to me 6) Why is this chick all about bathrooms? And why do so many of these stories involve peeing, while we’re at it? 7) Sounds to me like whatever bar you found this girl in wasn’t exactly going to yield you any classy or high caliber of woman (Not that any bar will, in my opinion).

If someone were inclined to say “I told you so,” (which I’d never do, of course) they might say that’s what you get for not setting the bar higher. Just a thought for next time. I realize sometimes you just want to go out and have a little fun, but if you end up with a pee-soaked couch and swapping hook up stories with your friends about the same girl in the same night, probably don’t be surprised. Better luck next time, man!THAT’S WHAT SHE SAID

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