I’ve been sleeping with one of my housemate’s girlfriends for a few months now.

I’m preparing to graduate and need to break off the relationship as peacefully as possible. It’s not as if we have any plans for the future or anything. Our relationship was just a random hookup that kept going because it was convenient. My question is how I can break it off with her without her getting too pissed off. I wouldn’t be walking on such eggshells, except I’m afraid she might end up telling my housemate, and he’s sure to be pretty mad. Although I’m not all that concerned about losing this guy as a friend, or this girl as a booty call, but I do, however, fear the possibility of an ass kicking for sleeping with a housemate’s significant other.

In all of this self-inflicted mess, I need to drop this girl, avoid my friend and somehow come away unscathed. I’m willing to take consequence for my own stupidity and the mistake I’ve made, but I don’t really want to do it from the confines of a hospital bed in traction.

The more peaceful solution you could offer the better.

– Help

He said:

Well, my answer to your question depends entirely on your own integrity. The way I take your question, the only thing that really matters to you is not getting your ass kicked. While that is an admirable goal by itself, if you cared about either the girl or your housemate, I would say your self-respect would be in question regardless of how you handle this.

The bottom line is, you forgot to remember something a wiser man than myself once said, “don’t shit where you eat.”

At the least I can say congratulations for getting this far without getting caught, but the kudos end there. All three of you have problems now. Your housemate and his girlfriend obviously need to sit down and talk after the smoke clears. Personally, I think cheating is the number one warning light in a relationship regardless of what the excuse might be.

It is entirely possible your housemate might thank you in the long run, after an ass kicking, for getting him out of a problematic relationship. However, when cheating is involved, people are rarely that rational.

And as much as I would enjoy casual sex with that much convenience, it’s a pretty big deal to not only hook up with your housemate’s girl, but to go beyond an isolated incident and keep the booty coming for several months.

If you care about any of the people involved, do the right thing. Sit down and try to have a rational conversation with your housemate and his girlfriend. It might be a good idea to have a neutral third party present to help prevent the aforementioned “ass kicking” you fear.

However, if you want the easy way out, and I’ll admit I would be quite tempted, wait until summer comes and you have some geographical distance between your housemate and his girlfriend. Then move your stuff out of the house and start looking for a new place.

Once you have that all squared away, I would call the girlfriend and the housemate. Although, I’m not sure in what order. I guess it doesn’t matter because if you call the girl first, and your prediction is correct, the first thing she will do is call the housemate. Then hopefully when you go back to school, they both will have had a chance to cool off, and you can move on with your life.

If you call the housemate first, just make sure he’s not going to hop in his bronco and find you Boba Fett style. In reality, he will probably call his girlfriend first, and she will encourage him not to beat you down.

However, while it’s not the happy-fun route, I would feel better about myself if I told them face to face, if I were in your shoes.

She said:

Well, well, well. We have a sticky situation on our hands, now don’t we. It sounds like you were getting the best of both worlds for awhile there. Actually, she was getting a pretty good deal herself. She was getting it from not only her boyfriend, but her friends roommate? This girl is my hero!

I have to applaud you guys for getting away with this for so long. But all good things must come to end, unfortunately. Since you are graduating, she has to be prepared for some sort of end to your random hookups. So personally, if I were you I would just be up front with her and tell her, and tell her it needs to end. Then again, since both of you are having such a good time, maybe you should bring this up after one last hookup, good-bye sex, if you will.

Here’s what you do. Expect the worst. Expect her to rant and rave. Expect her to throw a fist or two or spit out a few tears. And you might want to make sure nothing is is within reach when you break it to her just incase she wants to make a target out of your face. Trust me, I’m a girl. I know what we are capable of. So expect the worst and hopefully it will work out just fine.

Now your friend, her boyfriend. You have to be able to figure out how important your friendship with him is. Plus you are graduating. How often are you going to see him after you leave here? If you don’t plan on continuing the friendship, then screw it. Who cares if he’s upset with you if you don’t plan on being his best friend in the end.

Better yet, to avoid the problems, wait until graduation day to break it off with the girl. Then when she tells him you will be home free and never have to worry about the situation again.

If you plan on keeping the friendship after graduation, then all I can say is deal with it. He’ll be furious, probably for awhile, but he’ll eventually get over it. He’s probably not going to marry this girl because she has obviously cheated on him. Some time down the road he’ll realize a girl is a stupid thing to ruin a friendship.

Overall, I think it’s going to be practically impossible to get out completely clean. If you have to, wait as long as possible to tell her and you should be able to avoid a little uneasiness.