Jennifer Verti (Melissa Joan Hart), has spent all of her savings buying her first house and all of her belongings have recently been stolen while trying to move into her new house. Vince is a ladies' man and a gambler, and owes money to a debt collector known as "The Monkey" (real name is Eugene). They meet at a wedding, initially Jennifer dislikes Vince and begins to predict what kind of person he is, and as a result, he dislikes her. However they talk about weddings and are amazed by the cash and gifts a couple get, and consider how easy it would be get that kind of income. When Jennifer loses all her belongings along with the stolen moving van, she arranges to meet Vince for lunch and to suggest a fake romance and engagement, which he is very interested in going along with.