Pearl, a longshoreman's widow turned college freshman, enrolls in a tough class taught by an arrogant professor.

To compensate for cheating on a philosophy test, Pearl persuades Prof. Pynchon to give her an oral makeup exam, which evolves into a freewheeling battle of wits.

Scottish comedian Billy Connolly guest stars as Billy Pynchon, Stephen's long lost, scotch-swilling, blue collar brother, who is attempting to fulfill their father's last request - for his sons to reconcile and accept each other. Meanwhile, Pearl's study group forces her to drop out of the bowling league, much to the dismay of Joey and Annie.

Pearl's longtime friendship with Annie is tested.

When Pynchon's former university professor, who intimidated him when he was a student, shows up during class, Pynchon is reminded of what it's like to be speechless. After Professor Lockwood explains that he is in town for his book tour, Pynchon decides to read the new novel and is shocked when he discovers it's his own Oxford graduate thesis. Meanwhile, at open mike night, Annie performs her new country tune, ""Pearl"" - a song that is more an embarrassment than a tribute.

Unable to drive, Pynchon asks Pearl for a ride into New York City to see a play and she mistakenly thinks he's asked her out on a date. Once they arrive in Manhattan, it dawns on Pearl that Pynchon is planning to go to the theater with a friend and she is only providing the transportation. Fuming, Pearl leaves Pynchon stranded and unable to get back home.

When Carlo, Pearl's new classmate, falls hard for her and asks her to a dance, Pearl lies, saying she is already going - with Professor Pynchon, in part one of a special two-part episode. After Carlo admits that he'll be at the dance anyway, Pearl realizes she has to convince Pynchon to take her as his date - not an easy task. Meanwhile, the Caraldo household has the entire family over for dinner, and Amy Li invites her parents - Saul and Beverly Steinberg.

Dates for the grand homecoming ball hinge on a lost wager, an attempted bribe, second thoughts and, yes, fate.

When the University threatens to remove controversial books from its library, Pynchon is arrested for chaining himself to the library doors in protest, and his class is cancelled. Pearl then decides that she must join Pynchon in the fight against censorship in order to save the class, so she takes his place and chains herself to the library doors, taking the heat off the professor and freeing him to get back to the classroom. Meanwhile, Joey teaches Amy how to dance.

When Pearl, confused about what courses to enroll in next semester, asks Pynchon for advice on the subject, he recommends the services of a ""senior advisor"" - a 9-year-old genius. The tables are turned on Pynchon when, instead of Samantha advising Pearl on education, Pearl (with Joey's help) advises Samantha on how to be a kid. Meanwhile, Frankie is perplexed by the university's telephone enrollment system.

An attack dog that Pynchon's brother sent him for Christmas proves to be a bit overzealous and prevents Pynchon and Pearl from leaving the classroom on Christmas Eve. Pynchon and Pearl try to make the best of a situation neither wants to be in by decorating the classroom skeleton with ornaments and gathering snow from outside the window for a snowball fight. Meanwhile, Annie and Joey are stranded in their car during a snowstorm, trying to abstain from all the holiday food in the back seat, and Frankie and Amy Li are marooned together at the airport.

Prof. Pynchon's students have written papers on the abuse of power - and that's just what happens when he gleefully assigns them to grade one another's work. Pynchon tries an experiment on the students that turns the classroom into a war zone. The hostilities erupt when the professor decides it would be interesting to have the students grade each other's papers. Pearl and Amy end up not speaking to each other and Frankie tries to bargain an A for a date with Margaret. Meanwhile, Pearl tries to trick Joey into doing housework, but she's the one who ends up being duped.

When Uncle Bobo's widow Tina arrives to collect a $5,000 debt incurred by Pearl's deceased husband, Pearl fears she will have to drop out of school to pay it back. While Pearl tries to balance her finances and figure out how to stay in school, she discovers that the loan her husband took from Uncle Bobo was for the string of pearls he gave her as a 15th wedding anniversary gift. Pearl must then decide whether to sell the pearls to stay in school or keep the cherished necklace.

When Pearl, Amy and Frankie get stuck with a freak student nicknamed ""Weird Guy Bob"" who sabotages their group project, they end up using espionage tactics to save their grade. It isn't until after the project is turned in to Pynchon on paper that Pearl, Amy and Frankie realize that ""Weird Guy Bob"" has doctored their work to include his radical viewpoints such as ""kill the stupid"" and ""eat the infirm."" Joey comes up with a way to break into Pynchon's house and replace the paper - a plan that requires Pearl to be lowered through Pynchon's skylight with a rope a la Mission Impossible.

Unbeknownst to either Pynchon or Pearl, Annie fixes them up on a blind date for an important dinner at Dean Aston Martin's house and things really start cooking when Pearl turns out to be a dead ringer for the late Mrs. Martin. Pynchon, who is in the running for Chairman of the Humanities Department, is initially horrified to discover that Pearl is his date for the evening. He quickly discovers, however, that Dean Martin is charmed to pieces by Pearl and that this may actually sway the dean's decision. When Pearl and the dean get carried away, however, Pynchon attempts to defend her honor and the situation gets messy.

Outlandish dream sequences depict Pearl's attempts to write fiction, including a scenario in which she works on the loading dock at a hospital named for ER's George Clooney. When Pearl runs into a creative roadblock trying to write fiction, she decides to do some embellishing by incorporating her real life in the story, in part one of a special two-part episode. Alice Cooper guest stars as himself, playing Frankie's guardian angel. While Pearl is writing her roman à clef, Joey's ex-wife arrives in town, Annie is placed in charge of the loading dock, which now also functions as an emergency room; Amy tries to seduce Pynchon, and Frankie, after receiving guidance counseling from Alice Cooper, decides to major in heavy metal.

Pearl's work of ""fiction"" continues with Joey having a litter of kids, Annie becoming a star in the world of country music and Pearl romanticizing the image of her late husband, Sal. When Joey's ex-wife announces that she's pregnant - again, Pearl envisions a future with tons of grandchildren to raise. Then, trying to focus on her writing assignment, she continues to incorporate her own life into the roman à clef, casting a fantasy Sal as her late husband. The story also has Annie becoming the next Reba and Frankie considering the talk show arena.

Annie's ex-boyfriend and current pen pal, Freddy Rizzo, is released from prison, but her hopes to rekindle the flame are dashed when he discovers that he has more in common with Pearl. Annie is furious when Freddy, having arrived in town with a master's degree in the humanities, finds Pearl the more mentally stimulating conversationalist, but neither of the women is prepared when Freddy tells them who it is he really wants - Professor Pynchon.

Frankie's mother, Miriam Spivak, arrives in town and announces that she's left Frankie's father, but matters become worse when Pearl discovers that Miriam is having a fling with Professor Pynchon. After Pearl breaks the news, Frankie can't believe his horrible luck. Meanwhile, Joey decides to move out of the house and prove to Pearl that he can take care of himself - with a little help from Annie.

When Frankie decides he wants to be a documentary filmmaker, Pynchon allows him to turn in a film in lieu of a written term paper and Frankie's subjects turn out to be Pearl, Amy, Joey, Annie and Pynchon. Attempting to document ""jealousy, rage conflict - the real maelstrom of emotions"" by swaying each of his participants, Frankie tells Pearl, Amy and Annie individually that the film will be primarily about her. Unfortunately, when everyone gets together at Pearl's for a weekend filmmaking session, all the action is off camera.

When Pynchon's brother returns to town and asks Pearl on a date, Pearl questions his intentions. Although Pearl is attracted to Billy she isn't sure if he really likes her or if he is just trying to annoy his brother. Meanwhile, Pynchon starts acting strange after learning that his brother has asked Pearl out. Could he be jealous?