Tessa and her father experience culture shock when they move out of New York and into a house in the suburbs.

Surprised Tessa realizes she is attracted to her jock suburban neighbor; George feels pressured to throw the perfect barbecue.

Depressed that she has to spend Thanksgiving in the suburbs, Tessa convinces Dallas to take her to the city for a girls' day out. During their fun day, they run across George making out with a woman while he was supposed to be "working." Angry with George for lying to her, Tessa confronts him during the Royces' Thanksgiving dinner. Meanwhile Lisa refuses to wear a special dress Sheila picked out for her, so Sheila decides to literally turn up the heat.

When Tessa is asked to show new guy Josh Sherman around school, she becomes convinced that he's gay, when in fact he's an undercover narcotics officer. Lisa becomes deeply infatuated with Josh, and Tessa inadvertly convinces Mr. Wolfe to make special announcement to the student body. Meanwhile George re-evaluates his relationship with Dallas.

Tessa enjoys rubbing it in Dalia's face that Scott Strause chose her over Dalia. However the closer Tessa gets to Scott, the more nervous George becomes. When George discovers a box of XXL condoms that Lisa has given Tessa, he becomes obsessed and starts planning game night with her friends in hopes of keeping her at home more. Meanwhile Tessa soon discovers that the more time she spends with Scott, the less attracted to him she is.

When Tessa realizes that she's failing gym class, she decides to run for student body president in hopes of changing Chatswin High's obsession with sports. During the election, Lisa steps in as Tessa's campaign manager against Kenzie and Kaitlyn. Meanwhile, Ryan is injured during a wrestling match and finds himself mourned by his family, and George takes Ryan under his wing and introduces him to people who have moved forward from setbacks.

When Dallas's divorce is finalized, George becomes concerned and includes her in a shopping trip with Noah to buy a new mattress. Meanwhile Dalia makes a breakthrough in therapy with her psychiatrist, Dr. Richard Rohl (James Lipton), Lisa and Malik try to set up Tessa, and Ryan takes Tessa on a date.

As George and Eden's relationship gets serious, he decides to introduce her to Tessa, who is preoccupied with her job at Crystal Cup of Crystals. Meanwhile, George and Noah make a deal regarding George's relationship boundaries with Eden, and Eden is overwhelmed by Sheila's meddling and the Werners' overprotective behavior.

Tessa feels a void as Chatswin celebrates mothers; Dalia goes to Israel without Dallas; Eden reacts to a baby shower's theme.

Tessa returns to Chatswin after spending summer with her grandmother; George finds Tessa's renewed interest in her mother threatening; Tessa signs up for the Fall Follies; Noah and Dallas compete for Carmen.

When Tessa convinces Delia and her friends to think up feminist-inspired Halloween costumes, she attracts the attention of the Chatswin witch; Noah and George dress as each other; George misunderstands when Dallas asks him out.

Lisa agrees to help him with Tessa; Dallas invites her life coach along on her first date with George; Tessa baby-sits with Opus.

Tessa decides to spend Thanksgiving in the city with her mom and grandmother; George hosts Thanksgiving dinner for Dallas.

George assumes that Tessa will be thrilled to go on an excursion with her mother in New York, but Tessa finds herself missing Chatswin and her father; the Shay family is thrown into turmoil when Ryan finds out he was adopted.

When Dalia receives a new car after PSAT results are released, Tessa becomes obsessed with finding out Dalia's score; Jill and Noah ask Mr. Wolfe to tutor their baby.

George has to manage Tessa's recovery after her wisdom teeth are removed and deal with Fred Shay, who has moved into their basement after a career setback; Dallas is insecure about her relationship with George.

George starts to feel stifled when Dallas' efforts to promote his business go overboard; Tessa learns what life is like as a football player's girlfriend.

When Yakult feels depressed, Dallas asks Yoni (Wilmer Valderrama) for help; the Shays ask Tessa to set Lisa up on a date.

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 convinces Ryan to attend an art house movie with her on Valentine's Day; Sheila's mother, Gam Gam causes friction between Fred and Sheila; and when Dallas has a bad reaction to a cosmetic procedure, George has to enjoy an 18-course meal from renowned Chef Julio solo.

George is deeply affected when Marty passes away; after learning that Ryan has been dishonest, Tessa considers the future of their relationship and her plans for college.

Tessa helps Ryan choose a college; George asks Dallas to move in with him; Sheila sells George's house.

Dallas helps George tell Tessa that he has sold their house; when Dalia tries to make Tessa miserable, Tessa seeks revenge.

Sheila talks Mr. Wolfe into throwing a chastity ball at the high school; George buys Dallas her dream house.

When George lets himself go after the breakup, a worried Tessa calls on George's dad for help; Tessa learns Ryan will be bringing his new girlfriend home.

Tessa struggles with the budget while planning Lisa and Malik's wedding; June warns Tessa to stay away from Ryan; Malik turns to George when his family decides to boycott the wedding; Sheila gives Lisa advice.

When Tessa joins a knitting circle, the age of her new friends surprises George; George writes a song dedicated to his muse; Malik and Lisa bicker.