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When Me And My Boyfriend Broke Up, I Messed Around With His Best Friend

Source: Neil Beckerman/Getty Images

Almost two years ago I met this guy while I was waiting on line at the store. We’d never spoken before, but I knew of him in high school and he had a history of bouncing from girl to girl.

He’s very good-looking, charming, ambitious, and somehow he finds a way to make extreme confidence look sexy (as Remy Ma would say, “He got a reason”). When he approached me I knew what to expect from a guy like him. I figured he had way too many options to feel the need to be a ONE woman kind of man, and we’re youngin’s in our 20’s, so I didn’t expect a wedding ring. After a six month relationship I was in prior to, I just wanted to have some fun. No-strings attached, exactly what his type wants surprise, surprise.

Four months into our “relationship,” he decides that HE wants a commitment, and I’m reluctant at first, but gradually I warm up to the idea—It’s not as if I was sleeping with anyone else, he just didn’t know that— and our relationship turns serious.

—-> Enter stage left: HIS CRAZY ASS EX!! And by ex I mean ex-plaything. They were never in a committed relationship and she couldn’t care less about me until she realized me and homeboy was getting serious. She schemed and manipulated and stirred the pot in every way she could, and he ended up cheating on me with her one night after we got into a huge fight about me, “not caring” (I can’t win with this one. If I ask 21 questions and attack every floosy on his Facebook flirting then I’m an angry-nagging black woman, but if I don’t get jealous and I trust the guy completely then it means I  don’t give a -ish. WTF?!)

I didn’t find out about it until months later, but when I did I heard it from his best friend’s ex-girlfriend. She told me this right before letting me in on the fact that my now ex-boyfriend’s best friend– the one who always went out of his way to tease and clown me, had feelings for me, to the extent that she ended their relationship. The whole night was a soap opera in the making.

Now I’m sure you know exactly where this is going. I was upset and hurt when I found out, and on the night in question, more than a little drunk after the news. After I broke up with him and stormed out of the party, his best friend took me home . Tears led to hugging, that led to kissing, and we didn’t actually sleep together — I stopped it before it got that far–but he’s his BEST FRIEND of over 10 years, since childhood, so in a way I might as well have.

My ex has been begging me for another chance, and I love him. I really do. I understand that people mistakes — me with his BFF case & point—and, I’m willing to forgive him and work towards trusting him again, but I’m pretty sure he wont forgive me, or his best friend, for what almost happened. Even though we weren’t together at the time, I don’t think it matters.

I’ve accepted the double standard for myself, but I don’t want to be “the bitch” that ruined their friendship forever. But, I also don’t want to spend the next few years in the same room as them two without addressing it. They both have feelings for me and even if I did have a moment with his best friend –if I’m being completely honest, we have developed a close friendship over the past two years— My EX is the one I want to be with. Should I keep my mouth shut and hope his friend never says a word or confess? Is admitting a kiss really worth ruining two relationships permanently? Do you think my ex could get past it with either of us? – Ms. Damned If I Do Or Don’t

Dear Ms. Damned If I Do Or Don’t,

Chile, this is why I stay away from folks like you, and your “peoples.” All this drama and madness because y’all don’t know how to control your lustful and carnal nature. You are damn wrong. Your ex is damn wrong. And, the best friend is damn wrong. I see that ignorance is at an all time high.

If you knew the man had a history and past of being a player, a smooth talker, a charmer, and a history of bouncing from girl to girl, then what made you think that he would be oh so faithful and committed to you? Dumbass! I swear. You folks will rush to be in relationships with folks just so you can have a notch in your bedpost and to brag that you were letting them run up in you, but somehow and someway you were the one to tame them and make them commit to you. Really? Really! Miss Thang you are a damn trip in a half.

I do hope your ex finds out what you and his so-called best friend supposedly didn’t do. I hope you don’t believe that I really am that naïve and stupid to believe that you and the best friend didn’t do anything? I hope you don’t think that I’m a big ole’ donkey, like you, and will believe that you won’t hold that ace in your back pocket so the next time your boyfriend decides to bang some other chick, and you are soooooo upset and hurt, that you run right into the arms of the best friend for comfort? Girl, I’m not that dumb. I know how this game is played. I’ve been there, done it, and reinvented the damn game!

Your boyfriend’s best friend is not his best friend. Please, trust and believe, that if he has feelings for you, and made an attempt to sleep with you, that he has done this in the past with his friend’s girls. It’s a pattern, and he’s a sneaky ass low down snake. He waits in the grass, preying on all of the girl’s who were hurt and dumped by his friend, and he rushes in to provide comfort and a listening ear. Girl, wake your dumb ass up to this game and stop being played. Silly ass rabbit. They both are baiting you. Just like every other girl they’ve “played” with, and “toyed” with. All of you are just pawns in this game, and you’re so freaking wrapped up, talking about, “I love him.” Really, girl? Love? LMBAO!

Please do me a favor and grow the hell up and stop acting so freaking brand new. This childish ass antic you have going on is not cute or attractive. If you were a grown ass woman and lady, then you wouldn’t allow yourself to be used, played, and manipulated by two seasoned gaming ass little boys who don’t know how to be men or treat you with the respect and dignity you deserve. But, in order to be respected and treated with dignity then you must carry yourself in such a manner. And, you my dear, well…that’s up for discussion.

And, I know you like the fact that you have two men running behind you, panting, and having a pissing contest for your attention. You love it. You can sit in the room acting shy and innocent knowing that at any moment you can sleep with his best friend, and the two of you can have an affair behind his back. You love this game. Just know that the game will end one day, and you will be the loser. You may be winning now, but once your hand is shown and revealed, the joke will be on you!

Here’s what I suggest: Don’t get back into a relationship with your ex. It is doomed. It is a relationship and recipe for disaster. He doesn’t respect you, nor does he love you, or like you. No man who has a woman or lady will disrespect her by sleeping around with other women, and then come back home to you and lay up with you and run up in you raw. No man who has a woman or lady will accuse of her “not caring,” and use that as an excuse to go out and do whatever he pleases. So, why put yourself in these situations and predicaments where you can’t win? Why allow yourself to be deceived, manipulated, and lied to? Why play this game with him when he clearly has not grown since high school and he still thinks he’s the charmer, and ladies man? You can do bad all by yourself. And, then to add on top of it, his best friend is trying to sleep with you at your weakest moment. He’s trying to take advantage of you when you are vulnerable. If that’s what you want, and you like the fact that you have two men running after, then let the ghetto hood games begin.

But, I tell you this, if you say something to your ex-boyfriend about hooking up with his best friend, then don’t think that their friendship will end. He will dump you before he dumps his best friend. Men are not like women. Their boys can sleep with their girl’s, or exes, and they will still be best friends the next day. You will be ass out because your man feels that you can’t be trusted. You are the one who allowed yourself to be played by his best friend. You are the one who is a low down dirty whore. And, it’s you who should have resisted the temptation, and not let another man bang your back out, especially his best friend. Despite the fact that his best friend crossed the line, and despite the fact that you are his girl, men just don’t see it the same way as women. So, keep your mouth, legs, and every other orifice closed. Move on with your life, and remove both of them from it. They are not worth the game or time. You have so much more to offer, especially to yourself. It’s time to have some dignity, respect, and self-worth. It’s time to become a lady and woman and stop playing these childish ass little girl games. – Straight From Your Gay Best Friend

You can follow Terrance Dean on Twitter, HERE!

Make sure to get your copy of my new book,  Mogul: A Novel (Atria Books – June 2011; $15). It is available in bookstores everywhere, and on Amazon, click HERE!

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