Love Letters: Dating Your Friend’s Ex

friends and lovers

Since November is the time we #BlogLikeCrazy, that also means it’s a great time to blow through my backlog of relationship questions.

If you’re looking for wisdom from the Chuck Woolery of the Webz, this is your best bet to have your questions answered before the rapture.

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

Here’s today’s question:

If a woman or man began dating a friend’s ex, is that person obligated to tell the friend or should they tell the friend together?

Friends and Lovers

Props for realizing that yes, you should tell your friend if you decide to date his or her ex.

That’s what I did.

Journey with me back to high school, when Biggie Smalls was still alive and most of today’s “talented” rappers were merely neglected, dirty little infants. One of my friends was dating a very attractive young lady but that whirlwind romance didn’t last very long.

A month or so later, my phone rang — it was that young lady. I had no idea how she got my number but it’s not like I was complaining. She looked like a mini-Tisha Campbell — no brother would turn down that phone call.

We talked sporadically for about a week on the phone but, eventually, I realized that my boy had no idea that I was chatting it up with his ex. So the next day in class I told him that his ex-girl and I were getting close and if he was cool with that.

His reaction? “Eh, I don’t care.”

That’s also my response to every album TI drops.

Anyway, I’m still not sure if my boy really cared or was just graciously stepping aside. It didn’t matter in the long run — things never went anywhere with ol’ girl and me. High school romances tend to have a shelf life of like two weeks anyway.

If you’re dating your friend’s ex, yes, you’re obligated to say something to your friend. I’m not saying you need your friend’s approval of the relationship but, as a courtesy, you need to keep the air clear. That’s not the type of thing you want your friend to discover second hand on the street — it makes the relationship seem suspicious. And it would be nice if you and ex told the friend together, but, honestly, this isn’t about the ex. That person has no obligation to maintaining the friendship — that’s where you come in.

Clearing the air will go a long way to keep drama at bay.


Is having chemistry with someone overrated?


Um, is air overrated?

Without chemistry, your relationship is basically two people who live and do stuff together. You might as well date your roommate.

Chemistry is an important thing but it’s not the ONLY thing — and that’s where some of y’all mess up. Just because you have chemistry with someone doesn’t mean that person is destined to be your soulmate — respect, commitment, communication are important building blocks for your relationship as well.

Chemistry isn’t overrated. It’s absolutely necessary. But people have to realize that there’s more to a relationship than that.


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