You know what they say—you tend to see things a heck of a lot clearer when you look at them in hindsight. After experiencing almost 12 years of abstinence (which I'll get into at another time—I promise), one thing that I recognize is I had a pattern of sleeping with my guy friends.

Back in my gettin-it-in days, I wasn't the kind of girl who met a guy in a club and went home with them. I also didn't get down with one-night stands. In fact, 90 percent of guys I've slept with, I've known for several years (the others, no less than a year). After time spent hanging out had passed, I would build a friendship with them. Since oftentimes there was a chemistry and attraction, I would tell myself that sex with them wasn't that much of a risk. I knew them, so it was emotionally safe. Or so I thought.

But here's the problem. Out of my 14 friends/sex partners, ask me how many I'm friends with now. Hmph. When it comes to several of those past friendships, it's really a shame that we're not friends because, ironically, they weren't homie-lover-friends; they were literally my boys.

For better or for worse, whether we choose to acknowledge it or not, sex changes things. Oftentimes, in ways we would never predict or imagine. That's something I had to learn the hard way.

So, before you decide to sleep with one of your own homeboys (either for the first time or again), please take a moment to consider the following five things first. Because trust me, when it comes to having sex with a friend, it's really hard to undo what's already been done.

Why Do You Want to Do It?


Aside from being attracted to him, trusting him, and possibly being curious, what are your other reasons for wanting to "go there" with a guy friend? Sure, those initial three things may seem like enough of a motivator but looks can fade, trust can be broken, and curiosity has killed many cats (literally and metaphorically).

If you don't have a reason better than "I just wanna know what it's like," take a pass. While fantasizing about doing it may omit any consequences, once reality sets in and the deed is done, there's a good chance that one of you is going to be more into it than the other. And when that happens, things that used to not matter so much suddenly will. Things like, if you're both seeing other people, who your other sex partners are, and—what platonic friends rarely ask each other—where are things going.

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Are You Both on the Same Page?


It might ruin the potential of romance at the moment, but whatever. If you and your male bestie can talk about your relationships with other people, your credit scores, and how much money you both make, you can discuss what you both are expecting out of a sexual relationship. Not just what you both want in the bedroom but how you want things to roll afterwards too.

If there's one thing you don't want, it's to wait until afterwards to find out if one of you wants something casual while the other wants to explore the potential of something serious.

He's not a bad friend if you sleep with him, you catch feelings and he's not interested. But it could wreck your friendship if you don't explore things playing out this way beforehand. He's a friend, not some random. Your body, heart, and friendship are worth making sure you're both on the same page.

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Have You Accepted the Fact That It Will DEFINITELY Change Things?


Something that NONE of us can escape is the power of oxytocin. It's the natural hormone that our body produces during a kiss, cuddling, and especially during sex, that automatically makes us feel bonded to another individual. Some even call it the "love hormone" because of the powerful effect that it has.

If you're not willing to accept that one way or another, sex with your guy friend will change things, then you DEFINITELY don't need to do it!

For the record, it could also change things for the good. But either way, just from the doses of oxytocin you'll be getting alone, you can't exactly go back to how things were pre-sex. Pretty much ever.

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Do You Want Them to Be at Your Wedding Someday?


You might not care about it right now, but boooooy…this is a mental boomerang that you don't want to deal with later. Sure, having sex together may not seem like all that big of a deal now but that doesn't mean you'll feel that way 10 minutes, 10 days, or 10 months afterwards.

Also, if either of you end up meeting the love of your life and you decide to be totally transparent with them, they may not be too thrilled about knowing that a close friend knows you like they do. Yep. Even if you and your friend are cool with your past sex life, your future spouse may not be.

Keeping all of this in mind, if you and your friend are so close that you can't imagine them not being at your wedding or present in your life in general, this is another reason to reconsider having sex with them. Again, if not for your friendship's sake, the sake of your future marriage—with someone else.

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Are You Willing to (Possibly) Lose Them as a Friend?


So, why am I not friends with most of the guy friends I had sex with? Well, most of the reasons why, I've just shared with you in disguise as warnings. Some got married and their wife didn't want me in their lives. Sometimes one of us wanted more than the other. There were a few that wanted us to have sex indefinitely; me to only have sex with them but for our friendship to remain the same (translation: I could date other people, just not get sexually-involved with them). If I had one word for all of this? Mind-boggling.

And although some of my guy friends were the best sex partners I've ever had (no joke), if I could do it all over again, I would've stuck to the fantasy. Our emotional intimacy is what I miss more than the physical pleasure because a true friendship connection is really hard to come by. It made things so complicated that ending the friendship was the best way to make life simple again.

That's just one more thing you should seriously ponder before you decide to have sex with one of your guy friends.

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