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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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