The Ex's Best Friend

by Benjamin Todd — January 1, 2008

It makes sense, right? A and B get along, B and C get along, why shouldn't A and C get along? I've had some pretty extensive talks about whether it's okay going after your ex's best friend, and while the topic of revenge is usually on the forefront of people's minds, the idea that there's potential for a real relationship is one worth exploring.

"She" has been in and out of meaningless relationships for two years, and every time she would move on from her most recent misadventure, her thoughts would turn to the one that got away. It's natural to keep a special place in your heart for someone you cared about, so no one blamed her for mourning the loss of "him" when flings and things didn't work out. But in the latest mourning period, in the heart of the holiday season, she found herself hanging out with, and having a blast with, some of "his" and "her" mutual friends. A fantastic conversation started with "his" best friend that night, and hasn't stopped 3 weeks later. The guy she had always enjoyed having around, the guy who was always a good influence on the one she was with, the guy who always seemed to appreciate her more the one who was supposed to appreciate her most, was finally given the chance to move from the back to the passenger seat.

"It's like I've known him for years," she told me jokingly. They already knew everything about each other, and they already knew they loved each other; they just didn't think they loved each other THAT way. Some might say that the new guy is being a bad friend to his best bud, but the smile on her face when she's with her new man is enough to make you think twice about judging him.

I wouldn't have been a strong proponent for going after your ex's friends before I heard my friend's success story. There are a lot of complications and hurt feelings that usually are involved, but if you didn't break his heart the first time, you won't have to worry about doing it again by going out with his friend. If there's been enough time since the break up, if you know he's not just looking for some fun, and you're both ready to be with someone who you know you already care about, then go ahead and go after the ex's best bud...just don't rub it in when you run into your new beau's ex best friend.

Read all of Benjamin Todd's posts to The Dating Life.