Can You Ever Date a Friend’s Ex?

The question of the day from a reader: How long are you expected to stay loyal to a friend and not date their ex?

Interesting dilemma since both guy and girl code are pretty specific on this one point… Thou shalt NOT date a friend’s ex.

Notwithstanding the incestuous dating groups, most friendships have a hard time weathering the storm of when a current friend becomes interested in an old flame. Consequently, most of the people I know who value their friendships try to avoid the scenario all together. But what do you do when it seems that the statute of possession limitations has honestly run out and you think this guy or girl just might be your ideal drink of water?

This one is a challenging question for me to answer with any authority for two reasons… 1. I tend to be loyal way longer than expected and 2. I’ve never faced this dilemma personally. (I have, however, been hurt by a friend dating my ex. Well, honestly, my not-yet-ex. It sucked.)

I think it depends a lot on a few factors:

• How seriously involved your friend was with said “ex.”
• Is your friend “over” the ex.
• How long ago the relationship ended.
• How close you were to your friend when they were going through that relationship.
• How seriously you think the “ex” might be completely worth the risk.
• Does your friend bless it.

For example… if they were high school sweethearts, you have only recently become a good friend and your friend is in love with someone else… it might be time for your friend to gracefully give you the go ahead to date the ex. But if your friend just broke up with the ex, you were there through all the flames, shoulder to cry on, late night b*tch fests and “over it” isn’t exactly the phrase you would use to describe your friend’s feelings about their ex… maybe not such a good idea to pursue a relationship. If you want to preserve the friendship, at least have the grace to wait until the fires have died down and everyone has moved on with things.

Since this dilemma falls in the black/white category for some and all grey all the time for others, perhaps it would be wise to keep a few things in mind before embarking on a campaign to date the “ex:”

1. Before you do anything, really evaluate just how interested you are in the ex and ascertain if the interest is returned.
2. Talk to your friend before taking any action. The whole “it’s better to ask forgiveness than permission” idea does not apply in this situation.
3. If your friend is unreasonable (in your mind,) consider that you may lose the friendship by following your heart.

But in reality, it’s never very clear cut. So… just how far is loyalty required in order to be considered a good friend?