Sam works as a matchmaker, where she assists her clients with advice through earpieces during their dates. However, she has lost her edge after her parents' divorce. Additionally, her father is now getting married to his boyfriend, and the best man is her father's tennis trainer, Matt, who is very competitive. They soon find themselves in a bet where Sam has to succeed with her next client. However, Matt becomes overly involved in the challenge, which is particularly challenging as he was also the one who encouraged Sam's father to get divorced.