My boyfriend used to date one of my friends

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Dear Guys,

Okay, so I’m dating this guy who is like perfect for me. Well I found out that he and one of my friends used to “talk.” And well I’m not so much worried about how she feels about it because she has a new boyfriend, who she is like in love with. But well I know they used to talk, but he doesn’t know that I know. And well I feel weird dating him when he and my friend had a “thing.”

So what do I do? I want to stay with him because I really like him, but I just can’t shake this out of my mind….


Dear Sarah,

Thanks for your question.

You have no control over what happened before you arrived on the scene. But believe us when we say, we understand your concern. We don’t particularly relish the thought of dating each other’s past girlfriends. Guys especially have a hard time with this. But as we say to one another: Get over it! And that’s exactly what you need to do.

If you really like this guy you need to make a choice. Do you want to live your life controlled by your pride, or do you want to be open to possibility? You can’t have both.


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4 Comments on My boyfriend used to date one of my friends

  1. There’s this guy Tim I’ve been friends with for over 5 years, and we’ve only hung out a handful of times, but last year we got drunk, confessed that we were attracted to each other, and hooked up. He told me soon after this that it was a mistake we had sex and that he didn’t want to get involved. The reasons he gave me were that he was depressed and had trust issues due to past relationships going bad, and also that he was moving to the west coast soon. I was hurt, but told him that was fine and we resumed our friendship, even though there was still tension when we hung out. He moved, time passed and a couple months ago he was in town and invited me to hang out with him and his brother, John. So I did, and it turned out there was a stong mutual attraction between me and John. Tim did drunkenly joke to John about a sexual situation that happened between us in the past, and I told John later that I felt a little weird about all this, but it didn’t seem to bother him. But John and I have been going out since, (it’s turned into a serious relationship pretty quickly) I’ve met their other brother and dad, but Tim still doesn’t know about it, and John won’t tell him because he knows he likes me and is afraid of how he’ll react. (The only thing John told him was that he really likes me and that I gave him my number, and Tim seemed fine with it. But is he??)

  2. @Julia…..In the big scheme of things it doesn’t matter what Tim thinks. It matters more what you and John think. (And feel) In fact, typically, John would be the one to be upset that you had a fling with Tim, not the other way around. Guys don’t usually want to date a woman who slept with one of their friends, or even worse, their brother. But if John is truly cool with it, then great. Tim had his chance and he blew it. He made it clear that he didn’t want to get involved with you. (His reasons, whether valid or not, were just excuses. He could have dated you if he wanted to.) So stop worrying about Tim. He’ll find out sooner or later and it shouldn’t be a big deal. Focus on the fact that you have a great relationship going with John. Does this help? ps. Please share our site with friends, or on Facebook and Twitter, etc. Thanks. We appreciate it.

  3. Yes this does help, and I feel a lot better (although John’s still terrified of telling his brother!)I will definitely share this site with my friends, thanks!

  4. @Julia….Good luck and keep us posted. And come back anytime. We’re relaunching soon and we’ll be asking our audience to weigh in on questions using a multiple choice format. Hopefully you’ll come back with your posse and participate. Thanks!

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