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Mailbag: I Had Sex With My Friend’s Ex-Girlfriend, Now What?

This is a recurring TFM series. Catch up with all installments of Mailbag by visiting the archive.

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Is it okay to sleep with your best friend’s ex-girlfriend? If so, how long do you have to wait? I don’t think two months is long enough without explicit permission from your friend, which is how long our emailer waited before having sex with his big brother’s ex. In this week’s Mailbag, we’re taking a closer look at his situation.

His email is below.

Dorn/Dillon? (you really gotta pick one and stick with it fam), First, I want to start this off by saying your golf game is mediocre and your twitter game is trash.

So here is my predicament, maybe you can shed a little light on this and help me out.

So last night I got invited by this girl to come hang out at the local tavern and play some pool and have some drinks with her and some friends. Now this isn’t any girl, this is my fraternity big’s ex-girlfriend. Me and my big are super close, like thunder buddies close. We all hung out in a group and we knew each other (me and the girl). They only dated for about 3 months, but it just didn’t work out and they went separate ways and that was about 2 months ago, so it was kind of weird that she invited me out for drinks. But I accepted none the less.

I show up think that there will be a group of girls just giggling around and all that. Wrong, it is just her by herself at the bar. So I sit next to her and we talk and catch up, play some pool and its chill. 2 AM hits and we decide we can’t drive so we get an uber and she just immediately says that we are going back to my place. My thoughts were a little hazy at the time so I decided this would be ok.

Long story short, she comes back and we have sex (a lot of it), and it probably was the best sex of my life.

My question is, Did I break the bro code? Should I tell my big? He already has a new girlfriend. What do I do Dorn/Dillon?

Thanks fam


Looks: 7.5 out of 10, very fit, with a nice set of honkers, brown hair.
Personality: like a 4 out of 10, shes pretty obsessive crazy.

Also we snorted a shit ton of adderall (is that how you spell it?) in between drinks, idk if that makes a difference. Just some details.

Okay so I’m about to share a true story with you. The very first chapter meeting I attended — like literally numero uno after getting initiated — was solely dedicated to the removal of an older active member of the fraternity. My newly-initiated pledge class and I walked in on cloud nine, fresh out of pledgeship and beaming with curiosity, but were treated to the most uncomfortable hour of our young lives.

One of our actives went down on his pledge brother’s girlfriend, which is absolutely a more intimate act than intercourse. This guy was brought up in front of the judicial board and asked to testify. He came clean, reluctantly admitting to exchanging oral sex with his PB’s girlfriend, and he was booted from our chapter and was never heard from again. Exiled. It was an exhausting, dramatic, BRUTAL ordeal. The guy who was cheated on didn’t show his face in the meeting. He was too emotional. Too hostile.

Now, I know your situation is very different. They’ve been broken up for two months, so she’s technically available and free to pursue. I’m simply painting a cautionary tale for anyone facing temptation in dipping your pen in the family ink.

“My question is, Did I break the bro code? Should I tell my big?”

Yes, you broke bro code by hanging out with his ex-girlfriend without telling him beforehand. It’s not a felony like the situation I laid out above, though. We’ll call yours a class B misdemeanor. You two are very close, you say. Pay him his due respect. You should have hit him up before meeting her out. A simple “Hey, is it cool if I hang out with ______?” would have sufficed. But now that you already have, and now that you had “a lot of sex” with her, the proper thing to do is tell him about it with a hat-in-hand approach.

He’s going to find out anyway, and you do not want him hearing it from someone else.

P.S. I think it’s super weird when guys call each other “Big” and “Little.” That’s a sorority thing, man. I’m not totally sold on girls using those terms either, now that I think of it. Shit makes me uncomfortable.

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Dillon Cheverere

Dillon Cheverere (@DCheverere) is the Vice President of Media for Grandex, Inc. Email:

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