Ask Gossip Girl: Should I Date My BFF?

Blair Waldorf and Dan Humphrey in Airport

Photo Credit: The CW

Dear Gossip Girl,

I’m 22 and have been dating this guy for over a year and a half and its starting to get very serious. But there is this other guy, my best friend, who I can not stop thinking about. I hear that he loves me as more than a friend. I love my boyfriend and can’t imagine life without him–but I can’t imagine seeing my BFF date other girls. I get so jealous!

I’m afraid if I don’t try something with my best friend I’m always going to wonder what if. I don’t know what to do!




My Poor Confused Readerette,

There are a lot of good reasons to stay in a relationship–use of his private jet, a summer home in Nantucket, your very own black AmEx–but fear of being alone isn’t one of them.

Take a good hard look at your oh-so-irresistible BFF and ask yourself if you’re only smitten with him because he’s offering the one or two things your current man is not. If you ditched your BF, would you just end up realizing that your best buddy is just as lacking but in different departments?

When I’m facing a curious quandry, I “try on” a decision. Tell yourself you’re sticking with your current dude and see how that sits with you. If you feel icky and itchy, then decide in the other direction and see if that feels any more comforting.

Seems like you have two quality men vying for your heart…color me jealous, darling!


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  1. Daniel Carrillo Said:

    Don’t cheat on your BF obviously he is a good man for being committed to you. But if it does not work out absolutely date your friend! That is what a husband or even long term BF is a best friend. The only difference is you both decided to give each other a chance to see if there really is something.Feelings are important, but choose someone based on if they are a good man not if you feel butterflies or not. People should date those who have endured much with them. In other words a friend.

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