He's cute. He's fun. He's into you. The only problem? He used to be your friend's significant other.
Dealing with the ex-factor is treacherous territory. Even if your friend dumped him and especially if she didn't, going after her old guy can lead to bitterness, jealousy, or feelings of betrayal — and could put up a wall between the two of you.
The rules of the ex-games are as follows:
Talk to your friend first. It's just common courtesy to let her know your plans. All you have to say is, "Hey, I'm thinking about going out with Fred and wanted to see how you feel about it."
Feel out the ex to get his take on the situation. Any sign that he is still dealing with the end of his relationship with your friend is a sign to exit. He may have other motives in mind.
Be realistic. If your friend went out with him twice and is married now, she probably won't mind. If he was more important to her or if she's single at the moment, snatching up her ex is more likely to be seen as a stab in the back.
If it comes down to her versus him, consider your choices carefully. Although right now you may feel strongly about this new (to you) guy, remember that boyfriends come and go while good friends may stick around forever. Is it worth gambling your friendship? Is this guy really the one you've been waiting for?
It’s also important to examine why you are so attracted to this guy in the first place. Is it because he really could be Mr. Right, or is he more of a Mr. Right Now? There is nothing wrong with enjoying Mr. Right Now, but if all you want is a fun fling and some harmless flirting, then it might not be smart to risk the friendship of a good pal for a short, fluffy relationship. If you can really see yourself spending some serious time with the guy, then the stakes are different. You aren’t gambling a friendship on a lighthearted romance, but on a relationship that has major potential and could possibly change your life.
Also, regarding your friend, it’s easy to pay lip service and say you don’t want to hurt her feelings, but the truth is that many friendships can involve some type of jealousy or competition. If your friend is more of a frenemy and you routinely find yourself at odds with her, then you have to take an honest look at why you are so attracted to her ex. Is it because he really has a amazing sense of humor and great eyes, or is it because part of you is secretly happy that he finds you appealing over your friend? It’s hard to examine this side of ourselves, but the truth is that jealousy and even pettiness can arise even in the best of us, and it takes an honest, open woman to admit that she might not always have perfect intentions.
Ultimately, you have to make the decision that feels right to you. Go with your gut, but be smart about it.