Brianna, 21, has a hard time fitting into 61-year-old Bill's wealthy social circle; Katie dates one of her daughter's best friends; Rosie's parents are not supportive of her relationship with Drew; Brian is hesitant to mix with Gentille's 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.

Brianna confronts Bill about Kathleen's accusations; Drew asks a 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; Kate worries that Shawn isn't ready to settle down.

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 father 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 marriage; Gentille and Brian spend some time alone to focus on their future; Rosie confronts Drew about his playboy past.

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.