Ask Mish: My boyfriend slept with one of my best friends before we met. What do I say?


I’m a 25-year-old straight woman who needs help. My boyfriend and I have been dating for around three months. I met him through mutual friends and we hit it off right away. We get along so well, the sex is great and I love spending time with him. However, I recently heard that he had slept with one of my best girlfriends right before we started dating. This was just gossip, so I decided to go straight to the source and ask my friend. She said it was true. They had slept together a few times in what can be described as a “hook-up buddy” situation.

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She swears she had no real feelings for him and that he didn’t for her. I believe her. I mean, if they liked one another, they would be dating and I wouldn’t be with him, right? I’m not angry at my friend, and we have talked it out. What happened before I met him is not my concern, but I can’t help feeling stupid – like I was left in a dark. I don’t want to let this bother me, but it’s eating away at me. I think about times where we were all together and they had this big secret that I was just oblivious to. I feel like an idiot.

Do I tell my boyfriend I know or do I just leave it? How do I get over this? Help.

Major sucksville on your end, girl. Like a bad sunburn, this isn’t a life-threatening situation, just an irritating pain. You are going to have to practice some serious meditative control.

I just have to say one thing before I launch into how to deal with your boyfriend. I am very impressed about the calm, cool attitude you managed to retain when your friend let you know the truth. This is half the battle, so I applaud you, Miss Cucumber. Very impressive.

You have zero control over what happened in your boyfriend’s sex life prior to you, and like you said, had there been true feeling there, he would be happily shacked up with your girlfriend and not you. Yes, your friend knows what your boyfriend’s balls look like. Yes, she has seen his peaceful, snoring face. Yes, she may even know what it’s like to be cradled to sleep by his strong, warm big-spoon hug, but so what? There’s a bunch of other girls who have experienced this, too. Your friend did the right thing by being truthful with you when the time was right. I think it’s better that you initiated this, not her. Imagine the other option? You tell her about this new guy you are dating, how you like him so much, and winces her face to say, “Ummm, yeah I fucked him, like, six times last month.” Way worse! She didn’t tell you about the incident until you asked because she didn’t want to upset you over something so inconsequential. You both handled the situation well.

Now, what to do about Mr. Right Now. Personally, I would save this little nugget as ammo for the future. Whether you want to use it punishingly in one of your first real fights, or in a more light-hearted manner to just get to watch your movie choice that night, is up to you. (I vote light-hearted. The other choice is kind of psycho.) If you are going to bring it up with him, I suggest you do with that same coolness that you exercised with your pal. There is no point being mad at him about this. He wanted to have sex. Your friend did too. They satisfied an animal urge. They were probably drunk each time they did it. Big whoop. He wasn’t in love with her. You have to laugh this off. It’s so much better for everyone, especially you, if you can find the humour. It’s a powerful, juicy little nugget. Use it wisely, Miss Cucumber.  

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