Ask Lynn-Crazy About My Ex’s Pal

One woman wonders if she can approach her former boyfriend’s best bud. Here’s advice.

By Lynn Harris

ear Lynn,
I am 25, and my boyfriend of seven years and I recently broke up. We both realized that the relationship was not working and decided to end it. He was emotionally and verbally abusive and overall treated me with little to no respect.

The problem is that I am completely in love with his best friend. This is not a new thing. I have spent a lot of time with this guy, and I love everything
My ex is cool with this. He loves his best friend and wants us both to be happy.
about him. He makes me happy and is always a gentleman. My ex is cool with this. He loves his best friend and wants us both to be happy.

How do I approach the friend/my love interest? He would never want to cross a line. He does not know my feelings or my ex’s on this subject. Do you have any advice?
– Trying To Be Respectful

Dear Trying,
Wow. I was 100% sure your second paragraph was going to be about how you were afraid to break this news to your abusive ex, and I was going to have to tell you to be very, very, very careful. This problem is so much better than that one!

The one thing that gives me pause, before I go on, is that it’s a little surprising that your ex is so gung-ho. I mean, non-abusive exes go nuts at the prospect of their own exes dating their friends. Are you sure you have no reason to doubt yours here? Then again, I know full well that people who are abusive in relationships can have a Jekyll-Hyde quality; that is, when they’re good, they really are good. So I will give him the benefit of the doubt. (Instead of telling you to be very, very, very careful, I’ll just tell you to be careful.)

And now, on to the friend. Without the ex factor, this is your basic “How do I tell a friend I want more without ruining the friendship?” situation. And the answer, almost always, is this: You just tell
There’s no guarantee that things won’t be awkward for a bit.
them. What if, God forbid, they’re not interested? There’s no guarantee that things won’t be awkward for a bit — and if they really freak out, that’s due to something beyond your control — but what’s the alternative? As I like to say, you don’t want to be, down the road, the guy/girl at the end of the bar, nursing a drink and the pain of wondering what would have happened if you’d just confessed your love.

If you think a face-to-face revelation might be too much pressure, it’s fine to send an email or even a note. Something like, “I really treasure the friendship we’ve come to have. So much so that I almost hesitate to bring this up, but I find that I can’t avoid mentioning it. That is: Might you ever be interested in exploring something more between us? If you think you would, then I think I might, too. If not, no harm done. It was just important enough for me to ask. I hope I haven’t made you feel awkward. Please take as long as you need to get back to me.” In this case, you might want to add a P.S., as in “Out of respect for Larry, I’ve already run this by him, and believe it or not, he says he just wants us both to be happy.”

And so do I! Good luck.

Lynn Harris ( is co-creator, with Chris Kalb (, of the award-winning website — you can visit BG's blog to discuss this letter! A longtime journalist, Lynn has written about dating, gender, and culture high and low for Glamour, Marie Claire, The New York Times,,, and many others. She is currently the communications strategist for Breakthrough, a transnational organization that creates pop culture to promote human rights. Submit your own dating questions for Ask Lynn via Your question may be answered in a future column.
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