What To Consider If You're Going To Date Your Ex's Friend

I had a friend ask me the other day, was it okay to date or talk to a friend of their ex? Generally speaking, I always thought that if you had to ask whether or not you should date a friend of your ex, then you pretty much already have your answer.

One of the biggest reasons why it’s never been okay to date a friend of your ex is because it’s always been cardinal rule #1 of the friendship. You just don’t date anyone that your ex is friends with. But why?

How come I have to limit my dating pool because we no longer see each other?

Okay, fine. I get that part. But there are too many other factors to consider when deciding to go this route. You have to ask yourself, am I ready to deal with the backlash from the ex (if you still correspond) when he finds out that I’m talking to his friend? It doesn’t matter how cool he and his friend are now or how they were in the past. They still consider each other a friend, and you’re the odd man out. There are a few things that you need to think about when going down this road.

What is this really about?
Are you trying to get back at him for doing you wrong? Are you trying to make him jealous? Or do you actually like the friend and want to see where this could go? It could be said by someone on the outside looking in that if you felt like the friend was more to your liking or more compatible, then how come you didn’t date him first? You have to be honest with yourself and ask what is it that you really want to happen with this friend? Is it just going to be a quick fling? Do you want a relationship, or will he be just a “maintenance man”? If you’re honest with yourself, more than likely, you’re probably doing this hoping that your ex will come around and get his shit together and see that you’re worth having, but that’ll never happen. If your motivation is to rub your desirability in your ex’s face, the answer is clear—don’t do it. You’re using his friend, and if you really want your ex back, sleeping with his pal will hardly win you points. Even if you’re able to get an angry or jealous reaction now, trying to manipulate him will just make you the “psycho ex.” Tempting as it may be, ultimately you’ll find that forgetting about your ex is more satisfying and healthier than screwing with his life. 

Would I be judgmental of a friend who did this?
One good and definitive way to figure out whether this is a smart move to make would be to put yourself on the outside. Imagine that this is a friend of yours and they’re coming to you asking for advice on what to do. If you’d wag your fingers at them for being so bold, then that is a clear indication that your own conscience is warning you to stay away. If, at that time, you’re still wanting to move forward with this guy, try staying away for at least six months and see how you feel then. After the six month period passes and you two still want to try to see where things go, then bump it, go for it. If you don’t, then you’ve just saved yourself from confusing conflict with real passion—and wasting time on a not-right relationship. Note: If you do decide to go forward, some people will always question your motives and morals for getting involved. It’s not your job to try and change their minds—it’s your job to ignore them, rather than feed off the drama.

Is this worth someone’s feelings possibly being hurt?
We all have seen how things play out in the movies when something like this happens. It’s a great feeling for the two co-conspirators, while the ex is left in the dark… momentarily. Once they find out, it’s best to be prepared for what may happen. You can’t think that your decision will only affect you because it won’t. Whether you want to believe it or not, and whether the relationship was good or bad, 9 times out of 10, your ex is going to feel betrayed by both you and their so-called “friend”. You have to ask yourself, “Is my temporary moment of gratification with this person worth the feelings that I may stir up in my ex?” In the end, your ex may hate you and even the friend may harbor feelings of resentment for you because now his “friendship” is over because of their bad decision to move forward with you.

Can I deal with the idea of my ex and my new guy comparing notes?
Just like you talk to your girls about your guy, you don’t think this friend of your ex or any of their other friends about you? Why do you think the friend is so interested in you? It’s because he heard your ex talking about all the great and wonderful things you used to do to him and for him. Remember GUYS TALK JUST AS MUCH AS GIRLS DO!!! I’m sure he knows all of the details as to why you and the ex aren’t together anymore and so he’s got one leg up on anyone else. He knows what not to do before you guys even get started. If realizing that the friend knows way more than you’d like for him to know is a bit too much to your liking, then it’s best that you date outside of their circle of buddies and find someone else. If you don’t, you’ll be forever clung to the thought of your worrying about what you’re ex could be saying or has said to the friend, thus putting the friend in the middle of a more than already awkward situation.

After all of the soul searching, if you’ve got some hesitation still left, chances are good that diving in head-first isn’t going to make those feelings go away. Even though I believe you can’t control who you love, there are too many fish in the sea, even if your pond feels small at the time. It’s not worth it—I’d have to advise people to walk away. But if you still think dating your ex’s friend is the right move, then go for it. Sometimes, the minor relationships in our lives introduce us to the next person we date—there’s no reason your ex’s friend couldn’t be your soul mate.