Tuffy Luv Can’t Believe This Ashhole

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Dear Tuffy Luv,

A few weekends ago while my roommate/best friend was passed out in her bedroom, her boyfriend and I hooked up. The boy and I had been friends freshman year, and I had feelings for him before he started dating my best friend. He and I agreed that it was never going to happen again and to not tell anyone. Two days later, when we were both drunk, it happened again. I believe he is a good person, and loves his girlfriend so I told him I wasn’t going to say anything.

2 weeks later he tried to hook up with my best friend and my other roommate. She rejected him, but told me the story. Selfishly, I don’t want to tell my best friend, but at the same time I wonder if I was wrong about him, and he is hooking up with other girls. What do I do?

— Sex With Best Friend’s Boyfriend

Dear Sex With Best Friend’s Boyfriend,


Well, you’ve gone and done something totally unforgivable. You don’t feel bad about it at all. But now you’re trying to play the good guy and “warn” your “best friend” about her lying, cheating boyfriend.

Methinks the “lady” (HA) doth protest too much.

Giiiiiiiirl. Backstabbing is so not cute.

I might (MIGHT) have had some sympathy for you if it had happened once in a drunken fit and you had really never done it again. HOWEVER, what actually happened is, while your flooping friend was PASSED OUT, you effed her boyfriend. Not only did you not fess up, you made a pact with the guy to not tell her and then you did it again TWO DAYS LATER.

Guess what? You don’t get to play the good guy now. Oh, you feel so bad for her because she doesn’t know what’s going on. Oh, you’re such a good friend who made a little mistake and now has to make a big decision. Oh, poor your friend, it turns out the guy’s a sleaze, hadn’t you better do something about it?


More like: YOU feel degraded that it turns out he didn’t just find you so irresistible he HAD to cheat, but, in fact, he’s just a lying cheating sack. Tell her and come clean and expect your friendship to be over. I really don’t see how you two can come back from this. You completely betrayed her and you seem to have no remorse for it.

In fact, the only reason I say you should tell her is that I do think she should know about her sackboy. She may want to dump HIS ash too.

Good luck, jerkface.

Hearts & Skulls,
Tuffy Luv

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