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Your friend's robust social life can be hot until they flake on date night every new step you take in your romantic development is just no good. Many people think that dating a friend is a bad plan. “Aleeza, I can't date my friend, I don't want to mess up the friendship.” I think it can be a. Several years ago, I started dating my best friend. At the time, it made perfect sense. We were inseparable, we had so much in common, we.