Betting on the Bride (2017)

Health fanatic Melanie (Karissa Lee Staples) has backed out of not one but three weddings; the last one saw her flee from the church at the very last second. 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 whenever he wants. He takes a bet from his boss at the marketing company he works for that he can't meet a woman and get her to say yes within 30 days of meeting her. But when he meets Melanie, getting her to fall for him is harder than he thought; he complicates things by realizing that he has genuine feelings for her and then one of her exes discovers that Damon is only dating her as a bet.