How To Deal With A Seriously Awkward Roommate Situation

You never said you regret the hook-up, so do you regret that fact that you don’t have more of a relationship with him than you do? Regret is self-blame for a bad outcome, wishing you could undo something you did, or feeling sad about what might have been. Though it’s a heavy feeling, regret can help us become aware of what we want and don’t want, help avoid bad decisions, and give us guidance as we move forward in life. The emotions related to regret actually trigger our need for survival, and survivalist mentality avoids situations that are going to hurt us so it may be that you sense that this not-quite-crush is one-sided.

It’s very natural for two people who share a close living environment to develop a level of comfort. Boundaries easily blur with roommates as you get to know some pretty intimate details about each other. And, since you’ve probably spent many nights relaxing in the same space, my guess is that the hook up was the grand finale to many flirtatious encounters, so I'd encourage you to take a deep breath and figure out what was really going on when this happened. Were you lonely? Bored? Have you been attracted to him for longer than you care to admit? On the flip side, what was up with him? Was he into you? Only you can get those answers, but first you have to be honest with yourself.

You went from one set of rules to another and now it’s a game of pretending everything is okay. The reality is it isn’t or you wouldn’t care about him hooking up with someone else. Your peaceful bliss is now a hot mess with a big elephant in the room, and that elephant is not kicking in on the rent so you need to address it stat. It’s natural to want to avoid “the talk” because it’s uncomfortable but growing up means having to have those tough conversations even when we don’t want to, especially if any relationship with your roommate matters to you.

You can continue to ignore your discomfort but you risk your “crazy request” escaping when you least expect it. Your feelings will most likely surface eventually so if I were you, I’d acknowledge any awkwardness and just put it out there. If you have feelings for your roommate, how do you know they aren’t reciprocated? Neither of you have ever talked about it! But, if you truly don't want to date him, then it's not fair to ask him to not bring women home. Of course, it's helpful to get that thought out into the open, so have a knock on his door and see what’s waiting for you. Good Luck!