Dear Bossip: My Ex Cheated & I Kissed His Best Friend & Now I Regret It

Dear Bossip,

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 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 young, in our 20s, so I didn’t expect a wedding ring. After a six month relationship I was in prior I just wanted to have some fun. No-strings attached, exactly what his type wants.

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

Enter stage left: HIS CRAZY ASS EX! And, by ex I mean ex-play thing. 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, manipulated, and stirred the pot in every way she could. 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 flooy 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 it means I  don’t give a -ish. WTF?!)

I didn’t find out about the cheating 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, and 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 that he cheated. And, on the night in question I was 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. I was in tears which led to hugging and that led to kissing. 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, like me with his BFF, case and point. I’m willing to forgive him and work towards trusting him again, but I’m pretty sure he won’t 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 bish” 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? – Between A Rock & A Hard Place

Dear Ms. Between A Rock & A Hard Place,

Here’s what I believe and know – Your ex-boyfriend will eventually find out. You may not say anything, and you can pretend that nothing happened with his best-friend, but, at some point, it will come out and it will be revealed what happened between you and his best-friend. Thus, my rational is to tell your ex-boyfriend about the kiss. Nothing more happened between you two, and you didn’t sleep with him. It was a kiss. And, yes, your ex-boyfriend may get upset, and he may be angry, and he will be mad at the both of you, but just know that he will not end his 10 year friendship with his friend over you. However, it is a very real possibility that he will end it with you forever, and he will not want anything more to do with you.

You are a casualty of war. You know the saying “Bros before _______.” He will make you out to be the bad guy because you should have known better. You should not have gotten into the car with his best-friend after your fight. You should have resisted the urge to be with him alone and you definitely should not have been crying on his best-friend’s shoulder. He will see you as the one who should resisted his friend and had not put yourself into that situation and predicament.

But, I don’t know why you want to go back into a situation where he cheated on you. He betrayed your trust. He stepped out of the relationship and slept with another woman. Why go back? And, didn’t you initially state that you knew he was not the faithful type, and that he bounced from woman to woman? You were not looking for anything serious with him, and that you just wanted to have fun? But, I understand, and I get it. You hype him up as being charming, good-looking, and ambitious. He was the guy in high school that you had a crush on, and here was your chance to get him and have the wild and fun sex you’ve been dreaming about for years. Here was your chance to make do on your fantasy with him. I peeped what you said in your letter that you knew of him in high school but that you and he had never spoken. That’s code for your crush on him.

I also want to point out that you should not have been surprised when you learned that he cheated on you with his ex-fling who manipulated and schemed her way back into his life. You saw it coming. You put too much faith and trust in him to know that he could not resist the urge to sleep with her. Besides, you even stated, “I figured he had way too many options to feel the need to be a ONE woman kind of man.” You knew who he was before you decided to be in a committed relationship with him. You knew what you were getting. You ignored your own judgment about him, and still hoped for the best. Thus, if you get back into a relationship with him, then don’t be surprised if he cheats again. He’s shown you who he is, believe him. You know he can’t be trusted, so why go through this drama with him?

If you don’t want a guilty conscious, and you don’t want to bear the burden about kissing his best-friend, then tell him. It will nag at you, and you will never be able to be in the room with the both of them. You will always be worried about whether he either knows, or if he will find out. Tell the truth, get it off your chest, and be ready to deal with the consequences. And, no, do not pursue a relationship with his best-friend. Regardless of how much his best-friend may like you, want you and desire you. That is his best-friend. It will create more drama, more havoc, and more stress in your life that you don’t need. Move on with your life, and learn to follow your instincts and judgments. If your gut is telling you something about a man not being faithful, and you can’t trust him, and you have these early warning signs, then trust them so that you won’t end up in a situation like this again. – Terrance Dean

Hey Bossip Fam, what do you think? Share your opinions and thoughts below! Also, e-mail all your questions Terrance Dean:  loveandrelationships@bossip.com  Follow Terrance Dean on Twitter:  @terrancedean and “LIKE” Terrance Dean on Facebook, click HERE!

Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria   Books – June 2008); and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE!