Times have changed for Ellen, with Holly and Anita gone and Ellen now managing the bookstore on her own. While out with her aggressive, outgoing childhood friend Paige Clark, and Adam with his date, Ellen accidentally chips a tooth while opening a beer bottle with her teeth and has to go a dentist recommended by Paige. Ellen becomes attracted to him, but things go astride when she gets a whiff of the laughing gas that shows her true primal instincts. Meanwhile, Adam gnashes his teeth over a woman, named Joanna, whom he dates, dumps, dates again... and wants to dump ...
After crashing a show-biz party with Adam and Paige, Ellen learns that the whole event was for charity. So, she tries to make amends by going on a volunteering binge by packing care packages. But her obsession with doing good just makes her feel bad. Meanwhile, Adam becomes hooked on watching a new huge TV set Ellen won during the charity party.
Ellen is attracted to Dan, a customer whose visits to the bookstore every day spice up her life. But her rising hopes for a romance fall flat when she learns that he's a pizza delivery man who savors his work. Meanwhile, Adam buys a new couch for the apartment and has quite a time letting go feelings of the old one.
After discovering a hate note, a downcast Ellen stoops to hiring Paige to spy in order to root out and win over the malcontent in her reading group. When she learns that a man named Phil is the one, she learns that he wears a toupee and tries to win his respect. Meanwhile, Adam begins dating a woman he met over the phone in a wrong number situation.
Ellen goes out on a blind date set up by her eccentric mother with a certain Doug, whom she remembers from her childhood as a weirdo, but who turns out to be a perfectly normal guy and Ellen's eager to pursue the relationship. But after a series of complications, Doug is convinced that Ellen's the one who's strange. Meanwhile, Adam is chosen as a winner in a contest for women photographers and eventually poses as one. Also, Paige deals with losing Ellen's best suit jacket in her boss' car when it's revealed to have been stolen.
Ellen feels threatened by Adam's visiting friend, Theresa, whose witty humor rivals her own. But when Ellen sees that her own jealousy drives her comic competitor away, she literally hops on the same airplane to New York to makes amends meet to the dejected Theresa. Meanwhile, Paige's new boyfriend, Don, is reluctant to sleep with her because he wants to take things slow, in which the sexually aggressive Paige is not used to hearing from a guy.
When Ellen hosts a wedding-rehearsal dinner for her younger brother, Steven, and his bride-to-be, she unintentionally causes their breakup by revealing about Steven's previous engagement. So she doesn't stand on the ceremony when it comes to getting them back together and redeeming herself for her parents. Also, Adam tries to be the photographer for the wedding... if it ever comes off.
After Ellen throws a surprise birthday party for Adam, he becomes convinced that living with Ellen is limiting his potential in life. So, Adam gets a new job as the building manager of a retirement home and moves out of the apartment, leaving Ellen with limitless possibilities as to what to do with his vacant room.
To help Paige appease Ted, her demanding movie producer boss, Ellen poses as an exercise trainer. But when Ted offers Ellen a high-paying development job, Paige has a fit after feeling that Ted has no respect for her job in which she threatens to quit. Meanwhile, Adam gets a new job as the building superintendent and moves into a new apartment across from Ellen's and tries to hide from irate and demanding tenants wanting him for household repairs.
Ellen refuses to admit that she has a problem dealing with her wisecracking wit that gets her into conflicts. But after she finally expresses her anger to an elderly and rude lady living in her building, Ellen fears that her outburst has caused her sudden death. Meanwhile, Ellen hires a new daytime manager for 'Buy the Book', named Lloyd, and he immediately quarrels with Joe over tearing down the coffee shop to make more room for the bookstore.
Ellen does not want to hurt Audrey, so she reluctantly goes out to lunch with her, Paige, and Audrey's friend, Jessica, a travel writer. Ellen wants to get closer to Jessica, without hurting Audrey. So she lies resorts to lying to go to a party for Jessica in order to avoid going out with Audrey. Meanwhile, Adam inherits some historical family letters with some hysterical implications. Also, Joe has to swear off coffee after a doctor's visit that has diagnosed him with a stomach ulcer.
Ellen has a new boyfriend, named Greg, who is too nice. So Ellen tries to break up with him, but she cannot find the right time before Christmas and ends up at his house singing Christmas carols. Meanwhile, Joe and his new girlfriend, Stephanie, are scaring customers away with their on-again, off-again relationship. Also, Paige agonizes over what gift to get for her long-estranged, overly sensitive mother for Christmas.
Ellen goes on a scholastic trip to a museum with Adam and Paige to expand her cultural horizons where she meets an attractive English college professor. Desperate to win his affections, Ellen tries to impress him after he asks her out to a jazz concert and then to an opera. But when Ellen introduces him to the world of TV, his fixation on it makes their relationship boring. Meanwhile, Joe moves in the bookstore after having a fight with Stephanie.
Ellen is doing everything she can to keep the terminally annoying and obnoxious Audrey from moving into her neighborhood. Ellen helps Audrey locate a cheep house, but it gets destroyed in an earthquake, so Audrey moves in with Ellen. When Ellen moves to a guest house it burns down, then Audrey finds a place of her own... in Ellen's building. Meanwhile, Paige dates an alternate juror for a high-profile Hollywood murder trial, and Adam tries to catch a newspaper thief. Also, Joe tries to catch some rats infesting the bookstore, while the animal lover Stephanie objects ...
Paige persuades Ellen to relieve her job stress at a posh health spa she is going to for the weekend, which brings out tension between both of them over the painful massages, mud baths, and dinner schedules. Eventually, Ellen and Paige try to sneak out of the place for some "real food" but get literally get stuck on the fence surrounding the complex. Meanwhile, Adam tries to broaden his circle of friends, starting with Joe.
Determined to revive a childhood dream that her annoying and nagging parents, Lois and Harold, quashed, Ellen begins taking ballet lessons, being taught by Peter, and sets her sights on dancing the lead in her class recital and seeks more help in her dance moves with Adam who also took ballet lessons when he was in college. But on the night of the recital, when the lead ballerina sprains her back showing Ellen a certain move, she is forced to take the ballerina's place. Meanwhile, Paige begins dating a man from a karate class that dresses differently out of his karate...
After her apartment is robbed, a paranoid Ellen goes on a safety spree by taking personal defense classes from a police detective, purchasing trigger alarms, and even having a life-size dummy for protection. But her obsession with security makes her a model of insecurity to Paige, while Audrey tries to persuade Ellen to have a gun around.
Ellen and Audrey both have erotic dreams about Adam, but where as Ellen seeks answers with a therapist, Audrey vows to make the dreams realities. After being seduced by Audrey, Adam thinks it was a mistake which leads him to fake a relationship with Ellen.
At Adam's advice, Ellen reluctantly becomes a contestant on the TV sports show "American Gladiators." Ellen becomes smitten with fellow gladiator Nitro whom Adam tries to bond with. But on the day of the competition, Ellen becomes fighting mad when her female combatant, Ice, ruins her budding romance with Nitro. Meanwhile, Audrey decides to sue Paige after they collide with each others cars, and Joe tries acting nice to the customers after getting a hate note from an unknown regular customer.
After receiving a $5,000 tax-refund check, Ellen donates it to the Helping Hand charity foundation, much to Peter's delight. But when IRS wants it back saying it was a mistake, Ellen finds that Peter has already spent it to expand the charity fund. Meanwhile, Adam hires Paige to pose as various items for a new photography job he has, and Joe tries to make the coffee stand look more "American" due to his fears of being deported back to Canada dues to Ellen's problems with the IRS.
Ellen joins an animal rights activist group that stages an illegal protest of the killing of ferrets. When Ellen is thrown in jail during the protest, she lands in the custody of her annoying parents, Lois and Harold. After a few days, Ellen can't stand this and borrows her parents car and runs off with Paige and Adam to a rock concert, but afterwords is stopped by the police who claims that her parents have reported the car stolen.
Ellen feels guilty about lying to her mother, Lois, of not being able to have lunch with her in order to go on a ski trip with Paige and Adam. So, Ellen visits her therapist, Dr. Whitehead, who prescribes a dose of total honesty with her parents. But telling the truth proves to be more than the dysfunctional Morgan family bargained for. Meanwhile, Paige decides to take up a new hobby of skydiving, and Adam tries visiting a sperm bank to donate some of his.
Ellen rekindles a romance with Dan, the former pizza delivery man who returns after a six-month stay in Italy. But Ellen soon thinks that Dan is a drug smuggler after learning of his import-export business, and strange men that bring a package to her door. Meanwhile, Adam becomes hounded by Audrey's jealous policeman ex-boyfriend.
During a visit from her annoying parents, Dan finally clears the air with Ellen over his flour import business. Three weeks later, Ellen's relationship with Dan heats up after weekend long bed-in together, despite her getting cold feet about pushing on. Meanwhile, Adam finally caves in to Audrey's burning desire for him, and Paige feels left out in the cold when Ellen now spends all her time with Dan than her, which leads to all of them being at a movie theater where Ellen tries to patch things up between her and Paige.