Breaking “The Code”: Is It Ever Okay To Date Your Friend’s Ex?

4. Be Discreet?

Sometimes, the only way you’ll really know if the relationship is worth causing drama is if you start dating the ex-boyfriend secretly to see if there’s really something there. I know this sounds shady, and it probably is, but this way you can determine if this is a relationship that has real potential or if it’s one that will crash and burn so quickly no one will even notice. Start hanging out with him and tell him that you want to be discreet for a while before considering telling your friend or going public. I know it sounds like sneaking around (it is), but the last thing you want to do is tell your friend that you want to date her ex, ruin the friendship and then the relationship doesn’t even work out. Then you will have lost a friend and a guy? Know what’s worse? You’ll probably miss your relationship with her more than the potential one you had with him. If it doesn’t work out between you two, there’s a possibility you don’t have to tell your friend at all. But if things go well, then you’ll have to decide how and when you tell your friend that you’ve been dating her ex behind her back. Hopefully by then you’ll know that he’s worth it.