Take an incredibly wealthy individual, throw in a romance with someone from the opposite end of the income scale, and what do you get? A docuseries th…
21-year old Brianna has a hard time fitting in to 61-year old Bill's wealthy social circle and has a run-in with some of his friends. Katie tells her daughter that she is dating Kolton, one of her daughter's best friends. Rosie and Drew are in love, but her parents aren't in support of their relationship. Gentille questions her boyfriend, Brian, about why he is hesitant to mix with her group of friends.
As Brianna tries to fit into Bill's world, Bill arranges for her to meet up with his ex-wife to get advice. Gentille decides it's time to see where Brian lives. Katie's daughter confronts her about dating Kolton. Heir to a multi-million dollar publishing company, Sean and his fianc Megan meet with a wedding planner despite Sean's hesitation with getting married.
Brianna confronts Bill about Kathleen's accusations. Drew asks a big question that will change Rosie's life. Brian meets Gentille's friends for the first time, but it doesn't go the way Gentille hopes. Hopelessly romantic Kate worries her rapper boyfriend, Shawn, isn't ready to settle down and get married.
Rosie moves into Drew's loft without the approval of her family. Katie meets Kolton's parents for the first time. Sean finally tells his dad that he and Megan are getting married. Gentille throws a birthday party for herself.
Bill makes a decision that will change his and Brianna's life forever. Megan worries that Sean is having second thoughts about their wedding. Gentille and Brian spend some time alone to focus on their future. When Shawn flirts with fans after his big NYE performance, Kate gets worried. Rosie confronts Drew about his playboy past.
(Enhanced.) Brianna and Bill reveal to her family that they are moving to Miami. Katie, Kolton, and Julia travel to North Carolina to spend time with Katie's mother. Drew whisks Rosie off on a whirlwind vacation to New York. Gentille and Brian struggle to determine who wears pants in their relationship.
