Can't Buy My LoveAired on Jul 10, 2019
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.
Million Dollar ProblemsAired on Jul 17, 2019
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 e Megan meet with a wedding planner despite Sean’s hesitation with getting married.
My Secret Sugar DaddyAired on Jul 24, 2019
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.
Royal PainsAired on Jul 31, 2019
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.
No Pressure, No DiamondAired on Aug 07, 2019
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.
Bling in The Big AppleAired on Aug 14, 2019
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.
A Constructive ProposalAired on Aug 21, 2019
(Enhanced.) 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.
The Secret Is OutAired on Aug 28, 2019
Rosie has her bachelorette party and tells her friends the truth about how she met Drew. Brianna flies home to Dallas after a fight with Bill. Katie has doubts about her relationship with Kolton. Shawn surprises Kate for their one year anniversary. Gentille shops for her wedding dress and hears a shocking secret about Brian.
Diamonds Aren't ForeverAired on Sep 04, 2019
After Bill and Bri make up, Bill considers taking their relationship to the next step. Kate questions whether Shawn is the real deal. Brian moves forward with wedding preparations despite Gentille’s uncertainty. Sean seeks advice from his mom while Rosie and Drew head to the alter.
Marriage or Money?Aired on Sep 11, 2019
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.
Couples Journey So FarAired on Jul 29, 2020
This pre-season two special provides a look at what’s life’s been like for Bill and Brianna and Gentille and Brian since season one.