Ellen is approached by Tom and Larry, two hippie businessmen who want to buy her bookstore. But Ellen refuses to sell no matter how high the price. When Ellen decides to put down her roots and buy a home of her own, she's unprepared for the price. With Spence posing as her lawyer, Ellen pays a visit to Tom and Larry's office and decides to give in to their offer, but with the condition that she stay on at the head employee.
Ed Billik, Buy The Book's new manager, arrives and he and Ellen don't hit it off especially when Ed hangs a deer head in his new office, offending Ellen the nature lover and vegetarian. When Ed decides to fire Joe to cut costs, Ellen resorts to stealing Ed's deer head for ransom to get Joe rehired. Meanwhile, Paige and Spence finally negotiate a date of going to a baseball game. But nothing goes as they plan it.
As Ellen shows off her new house she plans to buy, as well as planning her father's retirement party at the bookstore, she becomes distraught when Lois and Harold tell her that they are separating. While the unhinged Lois and Harold reveals the news very calmly, Ellen becomes very unhinged which prompts her to make a run for it and ends up hanging on a letter of the Hollywood sign overlooking Los Angeles.
Ellen tries to get her parents back together by recreating their 1958 Cuban honeymoon. Ellen makes her house hot and humid, brings in palm leaves, and even invites Eddie Fisher over to sing for them, but sadly to no avail. After quitting law school, Spence gets a job at Paige's office and becomes downright rude to Barrett over his job as Paige's secretary. When Barrett quits, Paige refuses to associate herself with Spence until he gets Barrett back on the job.
Ellen begins seeing a new therapist to cope with the breakup of her parents. Claire, the therapist, tells Ellen that she needs to be more honest with people no matter if it will hurt them or not. But during a evening out for Ellen celebrating her mortgage approval, Ellen is shocked to find her therapist in a compromising situation in a parking lot.
While attending a camp reunion with Ellen, Paige plots revenge against Megan, a woman who Paige thinks put chewing gum in her hair 25 years ago (shown in a pseudo black-and-white flashback to 1971), and Ellen feels guilty because she was the one that put the gum in Paige's hair. Meanwhile, Spence thinks he's the target of a woman flirting with him, but the real target is Ed. Also, Gothic author Anne Rice signs copies of her latest novel at the bookstore on Halloween with Audrey and Peter in attendance.
Ellen's father, Harold, moves to his new bachelor pad, which is on the second floor of his house. When Ellen wants to spend quality time with him, they begin to quarrel over her interference with his life. When Harold injures his back and Ellen accidentally falls off a ladder injuring her neck, she must spend the rest of the evening caring for him, wearing a neck-brace, and dealing with a jealous Paige asking about Spence's whereabouts when he accepts a wedding invitation from an ex-girlfriend in Albuquerque, as well as an irate bookstore customer harassing Audrey. ...
Ellen's mother, Lois, joins a video dating service and goes out on a blind date with a man named Vic. But a wary and insecure Ellen tries joining the dating service too to find out more about Vic, which leads to Ellen following her mother and Vic to a country western dance club with the gang where Spence dances the night away with a local cowgirl and Joe becomes reacquainted with his old flame, Trisha Yearwood.
A pregnancy test leads Ellen, Paige, and Audrey to rethink their lives after their flings with their flames. As a result of a mix-up delay, one of the tests comes out positive and Paige thinks she's the one, then Ellen mistakenly thinks Audrey is the one and tries to come to terms with it, and Audrey's new stand-up comic boyfriend Mike. Meanwhile, a life saving experience at the hospital causes Spence to rethink his life of being a doctor.
On Thanksgiving, Ellen volunteers with Ed at a soup kitchen in feeding the homeless and becomes acquainted with a soup kitchen worker named Perry. Ellen then invites Perry over at her apartment for Thanksgiving, only to find out that he is homeless too which puts a damper on the dinner. Also at the party, Spence's mother warily meets Paige for the first time, and Peter misses Barrett after he leaves town to visit his family.
Ellen, Audrey, and Joe go out bowling with Ed where he gets angry after Ellen beats him at a game. So, Ed challenges Ellen to a game of pool at his house the next evening. After Ed beats Ellen at pool, she becomes the sore loser and they decide to put on the final test to who's the real winner with a final one-on-one bowling game. Meanwhile, Paige and Spence's plans to spend time alone together are constantly foiled as she's busy at her studio and he's busy with his new job as an E.R. doctor.
On Christmas time, Ellen and Paige plan a vacation to Mexico and leave Joe and Audrey to run Buy the Book for the holidays. When Ellen finds and takes in a stray dog, she decides to stay in town and care for the dog since no one else will and sends Joe in her place on the trip. But when Ellen's father, Harold, shows up at her apartment for a visit, he mistakenly thinks the dog is a gift for him and takes it home himself.
Ellen decides to go out more as part of her New Year's Resolution. However Ellen's plans for a solo grand dinner at a fancy restaurant doesn't go well as planed and she decides to take pottery lessons instead. Meanwhile, Paige's kitchen goes up in flames after Spence and Joe house sit for her while she's in Canada during a movie location shoot.
Ellen decides to add a new section onto her new house but has to wait nine months for a construction permit. Joe helps Ellen by asking his latest girlfriend, a wealthy older woman named Madeleine, for help since she knows some city officials. When Ellen tells Joe that she thinks that dating Madeleine makes him a kept man, Joe breaks up with her who responds by taking away Ellen's construction permit. When Ellen tries becoming chummy to Madeleine to give back her construction permit, Joe realizes that Ellen's bonding with Madeleine makes her a kept woman. Meanwhile, ...
After donating some blood to a blood bank, Ellen goes out with Spence to a wine tasting party where she gets tipsy from consuming too much wine and her outrageous behavior costs Spence the promotion he has been seeking when she offends his superior, the hospital chief-of-staff. But when Ellen returns the next day to apologize to the doctor at the hospital, he takes thinks the wrong way and makes a pass at her. Meanwhile, Joe writes jokes for Audrey's comedian boyfriend Mike. But Joe's Canadian humor falls flat with the American audience. So, Joe takes Mike to his ...
On Ellen's 35th birthday, she and the gang go to the rock 'n roll music camp in Hollywood where they get to jam in a band with David Crosby, Aaron Neville and Bonnie Raitt. But Ellen gets cold feet when she feels her singing can't compare with theirs.
Ellen helps Peter prepare a production of Romeo and Juliet done by deaf actors. Audrey, now single after breaking up with Mike, takes a liking to Brian, the actor who is playing Romeo. But as result of a misunderstanding of sign language, Ellen thinks Brian is making a pass at her. Meanwhile, Spence gets his signals mixed when Paige's former fiance, Matt, returns to the scene.
Ellen and Peter go on a spiritual retreat where he tells her that he feels that she is not has happy as others think, which offends her to a rare point of anger. Meanwhile, Paige thinks Buy the Book is the target of a robbery and she happens to be correct when she, Spence, Joe, and Audrey are all tied up together in the office for the entire weekend by the robber.
Ellen's hard-to-please, grandmother comes for a visit where she assumes Ellen and Joe are a couple, and that Ellen's parents are still together. But after a lifetime of white lies, Ellen and her mother finally decide to come clean with grandma. Meanwhile, Paige treats Spence to a weekend at Caesars Palace in Las Vegas which takes a turn for the worse when he hits his head after falling on the bathroom floor, winds up with amnesia, and spends the rest of the show wondering through the casino thinking that he's a Roman soldier out to protect Julius Caesar.
Ellen tries to speed up her parents divorce by showing them her example of free time in hanging out at a sports bar with Harold, and takes Lois to self-defense classes. But when Lois and Harold begin to have second thoughts after getting stuck in a traffic jam on their way to their lawyer's office, Ellen tries to reason with them, but she inadvertently brings them back together.
At Spence's advice to fill in some of her free time, Ellen volunteers at the hospital where she is assigned to care for an English Patient! When the badly burned man tries to talk to Ellen about his adventures before his accident, he is constantly interrupted by Ellen's recollections of the highlights of her life.
Ellen senses a kindred spirit in herself when she meets an openly gay woman, named Susan, through Richard, an old boyfriend of hers, who enlightens Ellen to her own sexual identity. Confused by this startling self-discovery, Ellen seeks the guidance of yet another therapist and braces herself for yet another moment of truth of her life.
Ellen decides to tell her parents about her sexuality. But for a person like Ellen, even the best laid plans go airy. While eating out at a Chinese restaurant, Harold and Lois (not surprisingly) don't react well with the news that their daughter is a lesbian prompting Harold to walk out and Lois to ponder this news. Ellen then convinces her mother to attend a gay support group where Lois expresses her feelings about the revelation.
Ellen tries to find out if Ed has a thing against homosexuals after he forces she and Audrey to take down a feminist display at the bookstore. Ellen's suspicions about Ed being a "homophobic" eventually prove correct when he tells her that he doesn't want her around his daughters that she is babysitting. Ellen then quits saying that she doesn't want to work for someone that is prejudice against homosexuals. Meanwhile, Ellen finally moves into her new house and tries to reconcile with Paige who's still shaken by Ellen's "coming out" revelation. Also, Spence asks to ...