Love Letters: I’ve Been Dating My Friend’s Ex. How Do I Break The News?


Cuffin’ season is in full swing! Get you one!

Well, get you one with good sense. I know that should go without saying, but I’ve been doing this blog long enough to know that’s rarely the case. So let me help out your love life. Here’s how.

Send your inquiries to, or find me on Twitter @etbowser. Just provide your initials, or a fun nickname. 

Here’s today’s question:

My best friend’s ex and I have been secretly dating for the past year. We don’t know how to tell her and I know that our friendship will be null and void. What should I do?


Back before I settled down and they hung my jersey from the rafters of the Player’s Ball Hall of Fame, there were a couple of instances where I had the opportunity to date my friends’ exes.

I turned them down every single time. Why? To avoid what you’re going through right now.

There are wayyyyy too many fish in the sea for me to dive in waters my boys have already been splashing in. Even if they give me their blessing (which happened in at least two instances) I STILL refused – there are too many opportunities to reopen old wounds or to trigger long-buried feelings. My friendships were more important than taking that risk.

Of course, lecturing you now won’t pull you out of the hole you’ve dug, so you only have one option:


I know that’s the last thing you wanted to hear but it has to be done.

The fact that you’ve kept this secret for so long will make the truth even more bitter for your friend to swallow, so that’s why you have to be as sincere as possible. And it would help if your beau is there when you break the news. Be honest and apologetic. If your friendship is strong, I think your friend will be forgiving.

But even if your friend is not forgiving, at least you can rest knowing you did the right thing.

That was a tough one. Here’s one more for the road:

So about nine years ago I was interested in a young man at my church. He wasn’t interested in me and married another young lady that was 13 years his senior. Fast forward to 2016 – he left the area with his wife. About six months ago his mother informs me that his marriage is on the rocks. They now have a 1-year-old baby girl. His mother says he asks about me a lot. He is filing paperwork for a legal separation. He has asked for my number. Now I’m feeling some type of way because it’s like what do we have to talk about? I wasn’t chosen in 2007 so what’s up now?


What’s up now, you ask?



Look, I don’t know the details of this dude’s relationship. Divorce sucks, and that often forces brothers to seek comfort. Clearly, he’s sees you as a safe space (thanks for ruining that phrase, Twitter) and is looking for you for solace.

But you’d better use caution. It’s been 10 years since you’ve dealt with the homie – people change, and there’s no telling if that change has been for the better, or worse.

Personally, I wouldn’t pursue him without first knowing his emotional state. If you wanna see what’s up, cool. But go into it knowing that he’s got more baggage than a Southwest flight.

Keep your heart, 3 Stacks, keep your heart.


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