After an unexpected break-up, Bobby's friends convince him to get out of his rut by leveraging his prowess with the ladies into a business as a wingman-for-hire. Meanwhile, Kristy - who's also just gone through a break-up - finds therapy and monetary success in defending women from sleazy male advances. When Kristy and Bobby take a sudden interest in each other, it's only a matter of time before one of them finds out that they're working for the competition.

Zach and Ben have been best buddies since they were in grade school. They were those "two guys" that we all know, opposites, but still the same kid. Their friendship continued through High School. Zach continually got them in trouble due to his carefree existence, and Ben was oblivious to everything as he became smitten by the girl of his dreams. Just as Ben got the nerve to pursue her, she moved out of the neighborhood, leaving Ben devastated for many years to come. Twelve years later, Ben & Zach, now in their mid-20's, still close friends, but have drifted apart due to making different choices in life. Ben is overworked and doesn't spend time doing the things he loves. He buries himself day and night in his work at a law firm. The only thing outside of work Ben has focused on is his life-long crush on the girl he met years ago in high school. Zach, an easy-going guy who enjoys everything he does...