Friendship or Love? A Guide to Hooking Up with a Friend’s Ex

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Dear Noah, 

My roommate has a huge crush on this girl but she’s shown interest in me and now I’m starting to develop feelings for her. Do I risk losing my friend to pursue this possible relationship?

–Bad Roommate? 

This type of love triangle can be a common issue between friends, but it’s increasingly difficult because you also live together. There are a couple things you want to take into consideration when trying to make your decision of what to do.

The first thing you want to figure out is whether or not this girl is worth it. Do you have real feelings for her or do you want a one-time-hookup? If you’re going to go through the headache of dealing with your roommate, you want to make sure you’re pursuing something that is going to last more than one night.

If you decide she’s worth it and you want to move forward there are a few steps you can take. First, you want to try and think whether or not this has happened before. Have you been out with your roommate in the past, and has a girl he was interested in come up to you? If so, how did he react? Did he laugh and shrug it off, or did he get jealous? Through reflecting on his past reactions to similar situations, you may be able to find an answer to how he may react if you go for the girl.

The next thing you want to consider is how strong your friendship is with your roommate. While it’s true that your roommate could continue to try and flirt with the girl, it seems like his efforts would be wasted if she’s interested in someone else. Don’t forget – when it comes to your roommate’s crush, the important thing is who she is interested in. The fact that she’s flirting with you suggests that she’s not into your roommate.

Then you have to go ahead and talk to him. Make sure to focus on her flirting with you as a sign that she’s not interested in him, and remind him that she’ll probably find another guy to flirt with if you pretend you’re not interested.

In the end, you’ll actually be saving your roommate the time he’d be wasting on a crush who isn’t into him. No matter who that crush happens to be flirting with, the important thing is that it’s not your roommate receiving her affection. Rejection is a hard thing to deal with, and don’t be surprised if your roommate displaces his anger about his rejection onto your relationship with this girl. Just remember that it’ll pass, and in the end you’re saving your roommate from wasting his time and going through a whole lot of heartbreak.


Dear Noah,

My friend and her boyfriend broke up about a month ago.  He and I have been hanging out a lot since then and recently we hooked up. Should I tell my friend at all or just keep it quiet? If I do tell her, when is the best time?

–Sneaking Around

The best time to tell your friend is as soon as possible. She’s just had a substantial loss in her life and is probably still upset over it. The last thing she wants to think about is her boyfriend hooking up with other people, but unfortunately he’s doing it…and it’s with her close friend.

When you tell her, she will definitely be angry. That anger, however, will mostly be from the fact that her ex has moved on and will have less to do with your dating him. If you keep this from her, though, she’ll have a legitimate reason to be angry with you. She can latch onto this legitimate reason, and her anger about her ex will be transferred to her anger about your hiding the relationship.

Definitely tell her, and do it soon. The longer you wait, the more deceived she is going to feel.  You may want to send her a Facebook message or note, as it may be better for her to be alone as she processes what has happened. You can express how conflicted you’re feeling, and that you want what’s best for her.

Give her the power in this situation, and tell her that she can decide what the best way is to deal with the fact that you’re hooking up with her ex. But if you want it to become something more with him make sure you don’t present breaking it off with her ex as an option, because that’s not going to happen. Although she may be extremely angry, her fragile state is no reason for you to stop a relationship that may end up being perfectly healthy.

Tell her, give her some time to react, and talk it out. You should fine, as long as you remember how hurt she is feeling and that she may place some of her anger about the breakup onto you. Remember that, and take whatever she says with a grain of salt.

Anonymously ask Noah your own hookup/dating/sex/relationship question below and you might find your answer in next week’s column. 

Also, check out Noah’s Twitter @Ask_Noah



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