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George is surprised by the age gap with Tessa's new circle of friends - a knitting circle. George, still whirling from his one night stand, chooses to write a song to his muse. Lisa and Malik aren't getting along.
Lisa and Malik's wedding is boycotted by his family, so he asks George to walk him down the aisle. Meanwhile, June warns Tessa to stay away from Ryan; and Sheila passes on some advice to her daughter on her big day.
Dallas is determined to help Dalia find her calling after failing to get accepted into college. Tessa is forced to double date with George.
Tessa mentors her new protégée, someone from outside of the cool clique, for the Miss Chatswin pageant to make a statement to Chatswin society. But Tessa's rivalry with Dalia finds her stooping to Dalia's level to win. When the guys go for a boy's weekend camping trip, Fred loses Victor in the wilderness.moreless
Tessa accompanies Dallas down South to attend Dallas' mother's funeral. George, Noah and Fred go on a grouper.
Lisa has decided to propose to Malik, but things don't go as planned. Not sure how to assist her, Tessa go to George for advice. Tessa makes a decision to fight for Ryan. George thinks his girlfriend is rude to her employees.
Tessa meets a male version of herself while at a college party with Lisa and Malik, and it's almost the perfect relationship. Dallas engages the services of a matchmaker to find someone for herself and Dalia. The matchmaker encourages Dallas to date herself, which leads to a makeover.
Tessa and George's pack to stay out of Chatswin culture is tested when George becomes captivated with the new juice bar. To overcome the pull of Chatswin, George takes a trip with Fred to Manhatten to remind him of what's real. Tess is coerced into attending Evan's birthday party which results in her revealing what she really thinks of him.moreless
Noah's back in town after completing a court mandated anger management program. George can't believe the new docile Noah is the real thing so he decides to test him. Tessa meets a free spirited band in the park who aren't what they appear to be.
After an encounter at the dog park, Dalia and Tessa help Dallas and George negotiate Chatswin to avoid any future awkward meetings. Lisa seems to be with Ryan's girlfriend, June, quite a bit of the time. Fred's worried that Sheila is pulling away from him.
Since his break-up with Dallas, George has let himself go. Tessa is concerned enough that she call's George's dad to come help, but the sage advice has the opposite effect. Tessa finds out that Ryan is bringing his new girlfriend for a visit to Chatswin.
With Ryan gone, Sheila and Fred take in a foster child named Victor. Resentful of this new mini-Ryan, Lisa sets out to make things hard for him. Tessa decides to put an end to George’s friendship with Dalia.
Determined to rebuild his relationship with Tessa, George introduces her to his new dog. But Sheila Shay is out to track the dog down. Dalia refuses to have anything to do with Dallas since she broke up with George.