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Dean Winchester and Castiel Novak have been friends ever since they met each other at the all night cookie shop in their freshman year of college. Now they're seniors, and while Dean is nicknamed "playboy" by everyone on campus and lives up to the name, Cas hasn't been on a date since sophmore year. One night, Dean decides to take Cas out, show him some moves, and hopefully help him get laid. The two of them have an amazing time, but one of them comes home thinking maybe they want to be more than friends after all.