The Ex Files (Part 1): Can I Date Your Ex?


Ever feel like you’re out of options to date a quality guy locally? Turns out, you just may be on to something. In fact, Frigyes Karinthy told us almost 90 years ago there’s only six degrees of separation. This makes dating a little bit challenging as no respectable guy wants to date someone’s “leftovers” inside of their social circle. But what happens if you meet someone and there’s such a magnetic appeal and attraction, you have no choice but to consider the possibility of dating the ex of let’s say maybe a friend or someone you’re close to? What do you do? Do you go in for the kill? Or do you do the diplomatic thing and fall back in line? Circles are small and the the quality of choices are even smaller. Is it worth it to ask a friend, “Can I Date Your Ex?”

Cory and I used to run the streets and shut it down at every turn. That was my dude and my absolute ride or die. I finally felt like I found a friend that I could almost call a brother—a confidant. Ironically, I’d encounter guys who would ask, “why are you friends with him?…you seem like polar opposites. He doesn’t have a good reputation.” I’d automatically go into defend mode and protect my friend’s name. I don’t allow anyone to speak ill of my friends—it’s simply unacceptable. But little did I know—they were just concerned—not disrespectful. Cory was athletically toned, attractive, and presented himself to be the kind of guy that blurred the lines of being full trade vs the ultimate power bottom. Keeping in line with being the polar opposite, we attracted different types of guys when we would hang out. He was all about body and I was all about brains. I found no reason for us to be competitive about the men we’d interact with nor did I think we’d intersect with the men we were into. That is until I met someone who possessed the potential to shower me with more than love.

Tony was a great guy. He was new in town from Houston and wanted to keep his options open as to be expected. We dated for a couple months and the one thing he was good at was spoiling me. It was very enjoyable, I’ll admit. But for reasons beyond our control, we both agreed our compatibility would be better suited in a platonic friendship. I was understandably pretty disappointed. Two weeks after we appropriated our relationship as platonic friends, he invited me to a party to celebrate his 40th birthday and I decided to bring Cory along. In the car ride to Tony’s loft, I confided in Cory the history and nature of our relationship. I even expressed the disappointment I had—even expressed a little hope of a change of heart. As we entered the party, Tony was obviously lively and was eager to meet Cory. They greeted and even had a side bar chat about a couple things they had in common. It was a great night! Fast forward to two weeks later. Tony and I play catch up. All was great in both of our worlds and it was just good to hear from him. “Hey, your boy Cory is actually a really nice guy!”, he says. I replied with a sense of agreement, “Yeah. He is. That’s my roll dawg for sure!”. He then very coyly responds, “We actually went on a date about a week ago and he is so funny. How did you two meet?” As one can imagined, my heart sank to the pit of my stomach. A WEEK LATER and Cory never mentioned one thing to me about Tony. Nothing! Betrayal was not my immediate thought. However, my first impulse: “BIIIIIIIITCH!” If there was ever a moment to back hand a bitch with baby powder in hand, this was clearly the time for it. I responded to Tony in a very matter-of-fact tone, “Funny?—I never knew he had the ability to be funny…at least not in the way that you mean it.” I immediately ended the conversation with Tony as there clearly wasn’t a need to continue.

They say keep your friends close and your enemies closer. Clearly, this is a statement from someone who embodies the art of war over the art of compassion. Is your friend an enemy if he wants to date your ex? No. Not really. But someone who keeps the notion from you and does it behind your back is PUBLIC ENEMY #1. Is this someone you want to keep “closer”? A person who blurs the lines of being both a friend AND an enemy? Doesn’t sound like a hard to decision to me. The fact is, if a friend is interested in dating an ex, asking directly if the person is fair game isn’t exactly a bad thing. We are all attracted to certain qualities in men and that is understandable. But there is also an expectation of trust in social circles and friendships. Once that is gone, let’s be very clear about what you have when trust is lost in any relationship—regret. We all know sometimes we may find ourselves in situations led by emotions we may not be able to control. Why make it harder by choosing not to communicate openly with someone we call a friend? If that communication happens and your friend doesn’t approve, move on. There are far too many other untapped fish in the sea. After all, is there really a benefit to compromise a friendship over an already broken relationship? Just do the math and you will find out exes are an ex…for a reason.


One thought on “The Ex Files (Part 1): Can I Date Your Ex?

  1. The Six Degrees of Separation within the community is REAL! If you ask me, “Can I Date Your Ex?” the answer will always be, “I’d prefer you didn’t, but you can do what you want.” I will then make the mental note if they pursue, and I will know just how to categorize this person; because if you are an actual friend, you would not want to date my ex. There are entirely to many options out there for you to be selecting from from my past. Maybe they may get along better than me and the ex, but I do not know if I am mature enough to watch them be happy together, so I may distance myself in the beginning and come back to the idea, but… “Why Him?”

    * I will say that this would have to be an EX, and not someone that I was “kicking it” with every now and then.

    Liked by 1 person

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