Patrick and Alex begin dating, but Patrick is unprepared for the chaos that comes with Alex's celebrity and wonders if he is in over his head. When he begins to lose his anonymity and is stalked by paparazzi, Patrick questions whether it is possible to find true love under the hot spotlight of the media.
For their second date, Patrick decides to take Alex dancing. Trouble is, he doesn't know how to dance, so he takes swing dancing lessons from Les, a burly dance instructor, in order to show Alex a swinging good time. But when Cheri informs Patrick that Alex can't dance, he decides to take Stevie's advice and take her on an expensive date befitting a movie star – which could end up costing Patrick more than just money.
For the first time in her life, Alex becomes jealous when she meets Molly, an ex-girlfriend of Patrick's, who is a sophisticated and prolific writer and doesn't know or care about Alex's movie star fame. But when Molly invites the couple to her book party, Alex uses a rather unconventional method to make herself seem more intelligent in order to fit in with Patrick's high-brow, former lover.
Alex is floored when she is offered the lead in a high-profile movie musical. But Patrick is torn about telling her the truth when he discovers that her singing voice closely resembles the sound of chalk being dragged across a chalkboard.
Patrick is elated when Alex invites him to spend a weekend with her at a luxurious hotel for a press junket to promote her new film. But after an encounter with some of the other stars' boyfriends, Patrick begins to feel like he may be losing his identity and becoming a kept man to the famous actress. Meanwhile, Stevie does what he can to help console an ever-depressed Cheri, who feels like a failure compared to Alex and her glamorous accomplishments.
The spirit of Halloween takes on a frightfully dull edge when Alex learns that director Leonard Heckman is planning on screening her first film, a poorly done, B-rated slasher picture. But Patrick and Stevie find themselves in a witch's brew of trouble when they try to stop the quirky director from exhibiting the movie. Meanwhile, Cheri finds herself attracted to a cute guy dressed as a bum for Halloween — not realizing that the man is really homeless.
Patrick reluctantly agrees to let Alex pose as macho action hero Kyle Britton's girlfriend – in order to stave off rumors that Kyle's gay – and then to stage a phony breakup. But an open mic backstage at a talk show could threaten to out Alex and Kyle's sham relationship and force Kyle out of the closet.
After Patrick inadvertently interferes with Alex and Cheri's relationship, Cheri quits her position as Alex's assistant and decides to follow her dreams of restoring the family boat — with some help from her sun weary dock-mate, Suds. But Alex begins to miss her organizationally challenged sister when she hires Bonnie, a highly qualified but socially inept new assistant.
Patrick is excited to have his hard-to-please mother, Rosalyn, meet his famous girlfriend during the Thanksgiving holiday. But when Rosalyn shocks Alex by telling her to break it off with her son, Alex decides to win her over by preparing Thanksgiving dinner herself — which could prove to be a daunting task since she doesn't know how to cook.
After agreeing to only spend up to $100 on each other for Christmas, Patrick is stunned when Alex surprises him with the key to a brand new sports car. For her part, Alex is speechless when Patrick's gift includes a key to his apartment, and Stevie discovers a newfound popularity with the ladies when he dresses up in a Santa suit.
Alex is a bit surprised when Patrick doesn't invite her to accompany him to his and Stevie's high school reunion. After overhearing a phone message from Laura — Patrick's high school flame — Alex begins to suspect that her mild-mannered boyfriend may be trying to hook up with his ex, and has to figure out a way to keep an eye on him during the party.
After getting Patrick a side job as a studio teacher to Dylan Cassidy — a demanding young actress in Penny Marshall's new film — Alex finds herself in an awkward position when Patrick unintentionally talks the diminutive diva into quitting the business, having told her that she's too smart to be wasting her time as a thespian. Meanwhile, Stevie has the time of his life when he accidentally locks himself inside Alex's panic room.
While Alex anxiously waits to find out if she has a chance of being nominated for an Oscar, Patrick convinces her to go away with him to a secluded spa to ditch the Hollywood scene and her demanding publicist, Samantha, during the announcements. But as Alex begins to relax, curiosity starts to nag at Patrick about whether his movie star girlfriend has been recognized by her peers and nominated for the prestigious award.
When Alex discovers that former friend and fellow actress Ivy Tyler has been released from rehab and doesn't have a place to live, she decides to take her into her home. But Patrick thinks Alex is making a huge mistake letting her wayward friend back into her life, as she still blames herself for ruining Ivy's career over a decade ago. Meanwhile, while setting up an Oscar voter's campaign at the Motion Picture Retirement Home, Cheri is mortified to meet a woman who has been her movie star sister's assistant for 60 years, and Stevie forms a bond with the elderly residents and finds himself taking on some of their traits.
After Patrick gets into an argument with fashion critic Joan Rivers over a trivial matter, Alex discovers that not one fashion designer will create an Oscar gown for her in fear that Alex and her garments will be thrashed by Ms. Rivers on the red carpet. But in order to rectify the situation, Patrick must seek the aid of Alex's ruthless agent, Elliot, whose solution could land the teacher in even more hot water.
With the Oscars just around the corner, Alex's nerves are put even more on edge when her domineering mother, Suzanne, shows up without warning and expects to accompany her daughter to the ceremony. This leaves Alex in the unenviable position of choosing between Patrick and Cheri as her second guest. Meanwhile, Stevie's decision to make a big impression on Alex at the awards gala doesn't quite go off as planned.
While trying to cope with her Oscar loss, Alex doesn't feel like leaving the house and upsets Patrick by refusing to accompany him to his own awards ceremony when he is nominated for Teacher of the Year. Meanwhile, Alex begins to wonder if her mother, Suzanne, is jealous of her fame.
Patrick struggles with the pangs of jealousy when Alex shares some steamy scenes with her new co-star – who happens to be her ex-boyfriend – and gives him the same double-peck kiss she gives Patrick.
Patrick learns the rules of dating famous celebrity Alex the hard way after unknowingly being interviewed by a writer, who turns the story into tabloid fodder. But after being read the riot act from Cheri, Patrick begins to become paranoid that everyone around him is a reporter snooping for a story.
To prove that he and Alex are just like regular people after being chastised by his co-workers, Patrick takes his famous celebrity girlfriend to fellow teacher Kevin's barbecue – and Alex turns out to be the hit of the party. But Patrick begins to sense that his friends are taking advantage of Alex's celebrity when she agrees to have the wedding of Principal Harris' daughter at her house, and the wedding guests end up paying more attention to Alex than to the bride and groom.
Alex finds herself at the mercy of one of Patrick's students when the kid stumbles upon a steamy, erotic tape made by the irresponsible couple. In order to get the tape back, Alex is forced to star in the student's high school musical production.
Alex and Patrick's relationship is put to the test when they decide to move in together. Meanwhile, Alex has a tough decision to make when she's offered a role in a film that's set for a long shoot in Italy – which would separate her from Patrick for quite some time.