In the Season 2 premiere, Tessa comes back to the suburbs after spending the summer with her grandmother in New York City, where she discovered her mother's musical talents, which she hopes to mimic in Chatswin's annual Fall Follies. Meanwhile, Lisa uses a secret about Ryan as leverage against her parents; and Noah and Dallas pull out all the stops in their competition to hire Carmen as a nanny.
Tessa persuades Dalia, Kimantha, Kaitlyn and Kenzie to wear feminist-inspired Halloween costumes, an idea which catches the interest of a notorious local witch named Paula. Meanwhile, George and Noah dress up as each other; and Dallas wants George to be part of her "Barbie and Ken" Halloween.
Lisa helps Ryan pursue Tessa after she feels guilty for not telling him that he was adopted, but Ryan mistakes her generosity for pity that he's seriously ill. Meanwhile, Dallas invites her life coach on her first date with George; and Tessa babysits Opus when Noah and Carmen go to the opera.
Dalia finds a new best friend in her father's fiancée, leaving Kaitlyn, Kenzie and Kimantha behind, but has a hard time dealing with their elopement, so Tessa helps boost her self-esteem and reunite her with her old friends. Meanwhile, Dallas and George's romance intensifies, though it's not exactly what George had in mind.
Tessa wants to spend Thanksgiving in New York City with her mother, who's en route from Berlin, and her grandmother, though the holiday doesn't turn out like she planned. Meanwhile, Dallas recruits George to prepare a feast, but he's going to need help from a professional.
After getting a makeover from Dallas, George is pleased with his new suburban look until some of his friends visiting from New York City consider it—and his girlfriend—as sources of amusement. Meanwhile, Lisa wants to spend time with Tessa with Malik out of town, but their mutual hankering for smoked fish gives Tessa a case of food poisoning.
George grants Tessa's wish to spend Christmas in New York City with her mother, but it's one she begins to regret coming true. Meanwhile, Ryan finds out he was adopted, turning the Shay house upside down; and Dalia's Christmas list includes Carmen.
When Dalia gets a new car for her PSAT performance, Tessa—who is treated to ice cream for hers—becomes obsessed with discovering her score, and ultimately their wounded relationship can only be healed by a hip-hop dance-off. Meanwhile, Noah and Jill want Mr. Wolfe to tutor their baby after a devastating rejection from the best day-care center in town.
Already busy helping Tessa recover from dental surgery, George has to put up with the hysterical behavior of Fred Shay, who hides out in the Altman's basement following a career setback. Meanwhile, Dallas begins to feel insecure about her relationship with George.
George needs some space when Dallas is overenthusiastic about his business, so he persuades Noah and Fred to start a band just for guys, but George breaks his own rule after he hears Sheila sing. Meanwhile, Tessa gets a dose of reality when she dates a football player.
Dallas' dog, Yakult, becomes depressed, so she calls on former flame Yoni to cure her, but George suspects the ex wants to rekindle their relationship. Meanwhile, Tessa helps Lisa get back in the dating game, but they end up on a double date with Ryan and Scott Strauss.
Dallas learns that part of her property is in East Chatswin, meaning she gets kicked out of the country club and Dalia must attend a neighboring high school. Meanwhile, Tessa is tapped to produce a Chatswin High TV show called "Teen Talk," but worries about her new responsibility when Ryan becomes the show's host.
Tessa persuades Ryan to go to an art-house film for Valentine's Day, but she's shocked by their reactions to the movie. Meanwhile, a visit from Sheila's mother drives a wedge between Fred and Sheila, who plots to get Lisa and Malik back together; and Dallas has a setback after a cosmetic procedure, forcing George to experience an 18-course meal from a famous chef all by himself.
Tessa begins dispensing romantic advice—whether people ask for it or not—though her attempt to help Mr. Wolfe doesn't work out so well. Meanwhile, George helps Dallas coach a T-ball team; and Noah and Dallas still can't see eye to eye.
The death of Marty profoundly affects George as he and Noah wonder what to do with his ashes. Meanwhile, Tessa examines her college plans and her relationship with Ryan, who may not be as honest as he seems.
Dalia helps Mr. Wolfe get over his breakup with Chef Alan by changing his appearance and, for good measure, plotting a little revenge to mend his broken heart. Meanwhile, Tessa lands an internship with Jill; and Carmen becomes the object of Noah's desire, much to Dallas and George's dismay.
George forgets a birthday gift given to him by Dallas, who's so worried that she doesn't measure up to Tessa's mom that she goes on an eating binge with Jill. Meanwhile, Tessa feels like she's getting old; and Noah learns a secret about his psychiatrist.
After his divorce, Noah lives with Opus in a fancy hotel until George convinces them to move in with him. Meanwhile, Dallas suspects that Dalia is a hoarder; and Fred asks Tessa for pop-culture lessons so he can land his dream job.
Dallas feels left out when George becomes obsessed with his body image to pose for a "Dads of Chatswin" calendar. Meanwhile, Dalia's friendliness toward Tessa makes Lisa think she has an ulterior motive.
Ryan depends on Tessa to help with his college choice, but her solution to his dilemma creates a window of opportunity for Dalia. Meanwhile, George asks Dallas to live together in a way that's devoid of romance; and Sheila tries out her new real-estate-agent license by selling George's house before it's on the market.