Dating a friend is widely recognized to be a pursuit fraught with potential complications. I learned this lesson the hard way when I started dating a friend in high school. Not only were we good friends, but our families were also extremely close and had been for years. When we broke up nine months later, all the usual post-breakup awkwardness and bitterness were multiplied tenfold by the fact that we were forced to hang out whenever our families got together, which was often. On the flip side, when we rekindled the flame after college, our friendship and the friendship between our families became one of the best parts about our more-than-friendship. We had a shared history, our siblings adored each other and we even went on a few joint-family vacations.
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The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He's been on more dates than you can shake a lengthy bar tab at, and he's here to help the average guy step his dating game up a notch — or several. I'm in a pickle. Over the last couple of weeks, I've been hanging out with a close friend's ex-girlfriend, platonically, after we ran into each other at Starbucks.
When your feelings are more passionate and stronger than what you'd expect from a normal friendship, it might be time to take things to the next level. Navigating this transition, however, is far from obvious. That said, if you act natural, communicate your feelings, and respect your friend, you'll find that you might start one of the most meaningful relationships in your life. Categories: Family Friends and Dating.