He Said/She Said - Swapsies
Brandon asks, "How long should I wait after my best friend breaks up with someone before I can date his or her ex?"
I know that, as a male, I'm supposed to say not ever in a million years. I know I'm supposed to say that once your best friend breaks up with a girl, that she will forever be forbidden to his closest friends – no matter how hot she gets. Traditionally, I know that dating the ex is taboo, and that Man Code section 19 paragraph B expressly prohibits men from exposing other men's weaknesses, especially if that weakness broke his heart and every time he sees her it only reopens wounds that no amount of time could completely heal. And as an absolute, I absolutely agree.
There are those who would argue that one man's trash is another man's treasure, and that if your best friend did the breaking up, it's his loss. If your best friend is putting sackfulls of pure gold on the curb to be picked up by the garbage truck, why NOT go rescue it from an unworthy end? But the people that say these things don't know anything about being a best friend in the first place. Lesson One: Loyalty.
There is much to be said for loyalty amongst friends, and forsaking all others for the benefit of your fellow man is exclusively what defines a best friend as "the best." It doesn't matter how perfect the girl is when your best friend is still in tatters about losing (or leaving) her. Girls come and go. Let her go. So more will come.
The only caveat to this kind of absolute adherence to social etiquette would be if your best friend and your dream girl had a limited relationship, because then you're not trying to prevent your bestie from experiencing heartbreak. If they weren't actually a couple – if they had an "open" relationship or admitted that they were just bed buddies or even if they were dating but it just never developed into anything substantial – well then there was no breakdown, and no heartbreak, and certainly no breakup. It would then be completely up to your best friend to decide how loyal he's going to be to you.
So you can never ever get with your best friends ex, but just because he didn't take a girl seriously doesn't mean you can't. How long should you wait if he never loved her or doesn't want her or has already replaced her? Three days. You know, so you can be sure she's had a bath.
To date or not to date the ex. That is the question, one that I'm sure has plagued many a dater. When it comes to love, however, nothing is really black and white. There is no right and wrong, no arrow pointing you in the right direction besides the beating of your own heart. So I guess the real question is, how much do you like this person? Human beings are complex creatures. We generally want what we can't have, because as we see it, the grass is usually greener on the other side.
The friend code on the other hand, is very simple. You do not date each other's exes. Period, end of story. Unless there is lots and lots of grey area. If they dated for less than three weeks, or if this "best friend" is one of 50 of your "best friends," then it comes down to how seriously into this person you are. It's important to never try and hide the relationship, but rather share your intentions with your friend before things become too fuzzy.
When thinking about previous relationships, there is always a part of you that thought they could be the one. When they fail is when you realize that they most definitely were not. Friendships have the potential to endure the ups and downs of the years. Is this ex worth losing your friendship over? The answer should always be no. So the only thing that remains to do would be to talk to them and use your spidey senses to determine how over this person they are. And while you're at it, find out why they have become an ex in the first place. You don't want to get stuck with a clingy mamas boy, when you could have uncovered that truth before the relationship even took off.