He's Spring City's hottest and most eligible bachelor attending A-list events with his small entourage, but what he really wants are nights at home with his off-limits assistant. She's tired of being the boss's third wheel and accepts an invitation to the MatchMaker's Valentine's Day speed dating event, even though what she really wants is him. When he learns he might lose her to one of twenty potential men, he makes a decision to cross a line that could cost them both personally and professionally, but will he be too late, and is the risk worth the reward?