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.
Brianna looks to find new friends in Miami, but after a night out, Bill questions her motives. Rosie grapples with the idea of eloping with Drew. Megan reluctantly sees a lawyer about the prenup Sean wants. Kate’s friend questions whether Shawn is the guy he says he is.
After Katie's breakup with Kolton, her daughter, Julia, plays matchmaker; Gentille questions whether to say "I do" or "I don't"; Bill plans a major surprise for Brianna; Sean's dad's disapproval jeopardizes Sean and Megan's wedding.