In the first season of this clever comedy, 16-year-old Tessa is uprooted from her beloved New York City and planted in the suburban "purgatory" of Chatswin. But the suburbs aren't all bad, as Tessa and her dad, George, discover - you just have to see things in a certain light.
In season two, as Tessa spends time away from Chatswin getting to know her recently resurfaced mom, who has been gone for most of Tessa's life, George battles a case of empty-nest syndrome. Could this be the perfect time for the bronzed, buxom and buoyant Dallas to strike on the newly single George? Meanwhile, Tessa is surprised to find that she and frenemy Dalia have something in common, and that Tessa actually misses Chatswin when she's not there. More specifically, she's surprised by who she misses. Could Chatswin be home after all?
In the season premiere, Tessa returns to Chatswin after spending the summer in New York City with her grandmother, and George feels threatened by Tessa's interest in her mom.
When Tessa convinces Dalia and the Ks -- Kimantha (recurring guest star ABBIE COBB), Kaitlyn (recurring guest star KATELYN PACITTO) and Kenzie (recurring guest star KARA PACITTO) -- to come up with feminist-inspired Halloween costumes, she finds herself the interest of the infamous East Chatswin witch, aka Paula (guest star RACHEL DRATCH -- Saturday Night Live, 30 Rock). As it turns out Paula isn't exactly what she seems. Meanwhile, Dallas invites George to be "Ken" to her "Barbie," but he declines, not realizing that she is asking him out. George and Noah dress up as each other. Recurring guest stars PARKER YOUNG, MAESTRO HARRELL and EVAN ARNOLD also appear as Ryan Shay, Malik and Chef Alan, respectively.
When Lisa feels guilty for not telling Ryan (recurring guest star PARKER YOUNG) that he's adopted, she agrees to help him pursue Tessa. Lisa's generosity leaves Ryan believing that he must be dying of "Ryan disease." Meanwhile, George and Dallas go on their first date, but in her nervousness, she invites her life coach, Tabitha (guest star H. JON BENJAMIN -- Archer), to join them -- which puts George off. Plus, Tessa agrees to babysit for Opus while Noah and Carmen (recurring guest star BUNNY RIVERA) attend an opera.
When Dalia decides that her dad's fiancée is her new best friend, Kimantha (recurring guest star ABBIE COBB), Kaitlyn (recurring guest star KATELYN PACITTO) and Kenzie (recurring guest star KARA PACITTO) are lost without their leader and turn to Tessa and Lisa for guidance. As Dalia struggles with her emotions over her dad's new marriage, she turns to Evan (recurring guest star SAM LERNER -- Rizzoli & Isles) for support, and it's up to Tessa to help Dalia return to her old self. Meanwhile, George and Dallas get intimate, but it's not really what George envisions.
When Tessa decides she wants to spend Thanksgiving in the city with her grandmother and birth mom, Alex (recurring guest star MALIN AKERMAN -- Wanderlust, Childrens Hospital) -- who is planning to fly in from Berlin -- Dallas decides to fire Chef Alan (recurring guest star EVAN ARNOLD The West Wing) and have George host Thanksgiving. But when George finds his cooking skills inadequate, he winds up schilling out cash to Chef Alan to help make the meal edible. Meanwhile, after missing Alex in New York, Tessa returns home to find a surprising Thanksgiving dinner. Recurring guest stars also include PARKER YOUNG as Ryan Shay and MAESTRO HARRELL as Malik.
When Dallas gives George a Chatswin makeover, he decides he likes his new look and begins to feel at home in the suburbs. But as soon as some of George's friends from New York visit, they start poking fun at his girlfriend and new life. In an effort to get back at them, George and Dallas make a pitch for the Scarsdale Performing Arts Center job that his friends are after. Meanwhile, Malik (recurring guest star MAESTRO HARRELL) leaves Lisa for two days, so she decides to spend every minute with Tessa. Part of their "girl bonding time" involves eating some smoked fish, which leaves Tessa in the hospital with food poisoning.
When George sends Tessa to New York for a Christmas excursion with her mom, Alex (recurring guest star MALIN AKERMAN), he assumes that he's given Tessa the best present ever. Tessa soon learns to be careful what you wish for, however, and she finds herself missing George and Chatswin. Meanwhile, Ryan (recurring guest star PARKER YOUNG) finds out that he was adopted, which throws the Shay family in turmoil. And for her Christmas gift, Dalia asks for Carmen. Recurring guest star TIM MEADOWS (Saturday Night Live) appears as Edmond.
When Tessa and Dalia get the test results for their PSATs, Dalia receives a new car as a reward; Tessa gets ice cream. Tessa is miffed that Dalia got a car, and becomes obsessed with finding out Dalia's score. The rift between the girls leads to an argument between George and Dallas, and the only thing that can help them is an old-fashioned hip hop dance-off. Meanwhile, Noah and Jill (recurring guest star GILLIAN VIGMAN) hire Mr. Wolfe to tutor their baby after the baby is rejected by the finest daycare in Chatswin. Recurring guest star TIM MEADOWS appears as Edmond. Recurring guest star PARKER YOUNG appears as Ryan Shay. Recurring guest star MAESTRO HARRELL appears as Malik.
When Tessa has her wisdom teeth removed, George struggles to manage both her recovery and the hysterics of their neighbor Fred Shay, who has taken up residence in their basement after a career set-back. Sheila suspects George of harboring rats, and Dallas feels insecure about her relationship with George.
When Dallas goes overboard making flyers for George's business, he begins to feel stifled and convinces Noah and Fred to start a "dad band" as a way to escape their significant others. Sheila catches the band during practice and impresses George with her singing, so he votes her into the band. Meanwhile, Tessa discovers what it means to be the girlfriend of a football player and incites a revolt. Recurring guest star PARKER YOUNG appears as Ryan Shay. Recurring guest star MAESTRO HARRELL appears as Malik.
When Yakult becomes depressed, Dallas invites Yoni (recurring guest star WILMER VALDERRAMA) back into their lives to help remove the negative energy. Everyone becomes enamored with Yoni except George, who believes Yoni really just wants Dallas back. Meanwhile, the Shays convince Tessa to help set Lisa up so she can get back in the dating game. The girls end up on a double date with Ryan (recurring guest star PARKER YOUNG) and Tessa's ex, Scott Strauss (recurring guest star THOMAS McDONNELL).
When Dallas realizes a portion of her property is located in East Chatswin, her life is thrown into a tailspin after she's kicked out of the country club and Dalia is forced to attend East Chatswin High. Meanwhile, Tessa becomes a producer of the Chatswin High TV show Teen Talk, but struggles with her new role when Ryan (recurring guest star PARKER YOUNG) becomes the host of the show.
When Tessa convinces Ryan (recurring guest star PARKER YOUNG) to attend an art house movie with her on Valentine's Day, their reactions to the movie surprise her. Sheila's mother, Gam Gam (guest star MARY KAY PLACE -- Big Love), pays the Shays a visit, causing friction between Fred and Sheila. The visit also spurs Sheila to try to get Malik (recurring guest star MAESTRO HARRELL) back together with Lisa. Meanwhile, Dallas has a bad reaction to a cosmetic procedure, and George has to enjoy an 18-course meal from renowned Chef Julio (guest star MICHAEL VOLTAGGIO -- Top Chef) by himself.
When Tessa becomes a relationship expert, she gives advice to everyone -- even people who don't ask for it. When she decides to help Mr. Wolfe, it leads to a sad realization about his relationship with Chef Alan (recurring guest star EVAN ARNOLD). Meanwhile, Noah and Dallas are still at odds, and George helps Dallas coach a T-ball team.
When Marty (recurring guest star JACK WALSH) passes away, George is deeply affected and Noah and George have to figure out what to do with his ashes. Meanwhile, Tessa learns that Ryan (recurring guest star PARKER YOUNG) hasn't been honest with her, and she has to examine the future of their relationship, as well as her plans for college.
Dalia takes Mr. Wolfe under her wing to help him get over his breakup with Chef Alan (recurring guest star EVAN ARNOLD). She convinces him to try a new look and plots to help Mr. Wolfe get revenge for his broken heart. Meanwhile, Tessa interns for Jill (recurring guest star GILLIAN VIGMAN), Noah is convinced Carmen (recurring guest star BUNNY RIVERA) is the love of his life and George and Dallas find themselves caught in the crossfire.
When George forgets the birthday gift that Dallas gives him, Dallas feels as if she'll never compare to his ex and she seeks solace in carbs and Jill Werner (recurring guest star GILLIAN VIGMAN). Meanwhile, Tessa believes that she has lost her youthful vigor, and Noah makes a shocking discovery about his psychiatrist, Bob (recurring guest star TODD LOUISO).
Post-divorce Noah and baby Opus take up residence in a high-end hotel until the Chatswin moms corner George and force him to intervene. George allows Noah and Opus to move in with him until they get back on their feet. Meanwhile, Dallas discovers that Dalia is a hoarder, and Fred enlists Tessa to teach him what's hip so he can land the job of his dreams.
When George agrees to participate in the "Dads of Chatswin" calendar, he becomes obsessed with his body image and alienates Dallas. Meanwhile, Noah, Fred and George all compete for Mr. December, and Lisa discovers Dalia's true motives after she buddies up to Tessa.
When it comes time for Ryan (recurring guest star PARKER YOUNG) to choose a college, Tessa endeavors to remain neutral even though Ryan begs her to decide for him. Tessa ultimately rigs his decision-making process, and Dalia uses this to her advantage. Meanwhile, George asks Dallas to move in with him in the most unromantic way and, as a newly licensed realtor, Sheila sells George's house before it hits the market.
In the first part of the one-hour season finale, Dallas offers to help George tell Tessa that he's sold their house and that they're combining residences, but it doesn't go as planned. The rift between Dalia and Tessa widens as Dalia goes out of her way to make Tessa miserable and Tessa seeks breakup revenge. Meanwhile, Noah obsesses over Carmen (recurring guest star BUNNIE RIVERA) even though she's dating his therapist. Recurring guest star PARKER YOUNG appears as Ryan Shay.
In the second part of the one-hour season finale, Sheila launches a chastity campaign in Chatswin and convinces Mr. Wolfe to throw a Chastity Ball at the high school, assuming that Lisa will be crowned queen of the ball. Meanwhile, George buys a house for Dallas and receives a visit from her ex-husband, Steven Royce (recurring guest star JAY MOHR), and Tessa sets up residence in her bathroom stall at school. Recurring guest stars include PARKER YOUNG as Ryan Shay, MALIN AKERMAN as Alex, MAESTRO HARRELL as Malik, DEENA DILL as Bliss and DYANA LIU as Wan'Er.