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 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.

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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.