I Slept With One Of My Boyfriends’ Best Friends. Should I tell Him?

Dear Blackman,

I started dating someone that I have known since college. I am attracted to the person and would like to pursue a relationship him. A few years back I slept with one of his best friends. I am not sure if he knows or not. Should I tell him?

-Sarah

The Blackman:

Hi Sarah,

If you are looking to pursue a relationship with this guy then you should tell him. That can be something very crucial in his decision to be in a relationship with you.

Some men are very particular about dealing with a female that has slept with any of his friends, especially if it is really close friend.

If you don’t tell him now it could easily come up later on, and he could have severe trust issues with you assuming that you’re being shady and hiding other stuff.

Another thing to also consider is that he may already know since it is a close friend of his. He may be sitting back waiting to see if you are going to come out and say anything about it. The way you handle that could dictate how he may want to move forward in dating you.

I would be upfront about it. No matter what the result is, it will save a lot of drama.

I hope this helps. Good Luck.

TBM