As the saying goes: you can pick your friends, you can pick your nose, but you can’t pick your friend’s nose. Nor can you pick your friend’s ex as your new boyfriend or girlfriend. Sure, no one can officially tell you who to and who not to date. We all try to take the advice from our friends, respect the wishes of our parents, and listen to our instincts, but figuring out who is the right fit for us romantically is a trial-and-error process each time. If you find yourself on the verge of dating the ex of one of your friends, it’s time to think rethink. Maybe the pros and cons of seeing someone your friend used to date can help you decide. 

Pro: It’s high school—your options might be limited. If you’re in a situation where you and someone else are attracted to one another it can be a lot to ask to just walk away.

Con: Your decision might make the rest of your friends feel like they have to choose sides—it’s either you or your buddy. Going after someone’s ex is rather taboo and the chances are high that everyone will think you’re the bad guy in this situation. Now you’re not just losing the friend that used to date this person, you’re gambling with many of your other meaningful friendships.

Pro: You already know you enjoy spending time with this person. They hung around while they and your friend were dating. If you liked their company then you know you will now as well.

Con: This will probably ruin your friendship. High school relationships don’t often have the friendliest endings. Whatever drama came with your friend’s breakup only becomes amplified when you pursue the ex. Even if they say they don’t mind, there is no way they don’t feel at least a little bit betrayed. 

Pro: You may have witnessed parts of their relationship that you feel you can do better. It’s no fun watching someone you like in a relationship that isn’t right for them when you think you could make them happier. 

Con: Dating relationships usually don’t last as long as friendships. Even if the two of you are totally into each other the odds that this romance lasts for the long haul are slim. When you treat a friend right in high school, they’re likely to have your back for the rest of your life. When you go out with someone in high school things are inclined to fizzle out over time. Which one sounds more valuable to you?

At the end of the day the decision is up to you—and if you think you screwed up and didn’t make the right one you would not be the first person in the history of high school to feel that way.

Coming next: Part 2. Dating Your Ex’s Friend(s)!