Health fanatic Melanie (Karissa Lee Staples) has backed out of not one but three weddings with the last one seeing her flee at the last minute from the church. It is why she has decided to ignore men for a while and focus on her business with her sister. Damon (Peter Mooney) is a committed bachelor who mocks all his friends who have settled down and had children but is confident that he could seal the deal when ever he wants. It is why he takes a bet from his boss at the marketing company he works at that he can't meet a woman and get her to say yes within 30 days of meeting her. Trouble is that getting Melanie to fall for him is harder than he thought and then he genuinely starts to have feelings for her which complicates matters especially when one of her ex's discovers Damon was only dating her as a bet.