Ellen Morgan, a 32-year old, wisecracking, insecure single woman who lives in Los Angeles and works at a bookstore called "Buy the Book," deals with a crisis when she tries to get her awful drivers license photograph changed. Meanwhile, Holly, one of Ellen's friends, is dating a new guy, named Roger, and Ellen fears that he will dump her after Holly sleeps with him. Rounding out the friends are Adam Greene, Ellen's sloppy, sarcastic roommate, and Anita, Adam's one-time, smart mouthed girlfriend.
Ellen cannot stand Audrey Penny, a terminally annoying and obnoxious friend that she's been trying to dump for years. But when Audrey accidentally overhears Ellen's true feelings towards her over the phone, a guilty Ellen tries to win her back. Meanwhile, Holly puts on a false breast front to impress a new man she is interested in.
In an attempt to freshen up their dating lives, Ellen, Adam and Holly answer personal dating ads in the newspaper where Holly meets a neurotic recently divorced man, Adam tries honesty than exaggeration, and Ellen meets Jackson, the man of her dreams. But when it comes to kissing, Mr. Right is all wrong and Ellen cannot seem to tell him about it.
Ellen goes to her 15-year high school reunion were she poses as a wealthy cardiologist marred to Adam in order to show off to her former classmates, which jeopardizes a romance with a former high school heartthrob she also meets there. Also, Holly feels left out when Anita gets all the attention during the reunion dance, while Adam tries to hook up with a building manager to arrange a move into a rent-controlled apartment.
At her mother's advice, Ellen tries kissing up to her no-nonsense bookstore boss, Susan, by buying a gift for her newborn baby. But Ellen's job is threatened when she makes disparaging remarks about Susan's baby and her maid overhears this who makes the threat to Adam. Meanwhile, Holly and Anita plan to travel to Mexico to buy some paintings to sell them to a shady art dealer for large sums back in Los Angeles.
Ellen begins dating a younger man, named Tim, who makes Ellen feel old and uncomfortable about herself. At the advice from Joe, Ellen sets out, with Holly in tow, to a hip clothing store in an attempt to act cool to the 24-year-old Tim. But Ellen's attempts to be cool leave Tim lukewarm.
Ellen's boss, Susan, is looking for a date to a family wedding and Adam convinces her to bring him along. But Ellen does not expect both of them to get really intimate. When Susan and Adam individually tell Ellen that they are not right for each other, Ellen tries to play cupid for her boss and roommate.
Ellen's cousin, Tracy, arrives in town for a visit and that's only the start of incredibly bad troubles that happen to both of them in an attempt to make Tracy's vacation enjoyable. But when Tracy mistakenly thinks that Ellen has sabotaged her vacation, she flees town with a notorious motorcycle gang, and Ellen, Holly, and Adam set out in hot pursuit of them.
Anita offers to buy Ellen and Adam a new refrigerator with her employee discount from the merchandise store she works in. But when Anita begins dating the appliance section manager, she, Ellen and Holly have to keep moving the new refrigerator to and from Ellen and Anita's apartment again and again to make it seem Anita owns it which turns into a major hassle. Meanwhile, Adam slightly injures his back in a minor car accident and his ambulance-chasing doctor suggests faking pain for a potential lawsuit against the insurance company.
Ellen needs a new car, so Adam gives her some aggressive bargaining tips. Ellen is so good at it that she gets Glenn, the weak-willed car salesman, yelled at by his employer for selling the car so cheep. Afterward, a guilty Ellen hires Glenn at Buy the Book after she mistakenly thinks she got fired. Also, Ellen's overbearing and obnoxious parents, Lois and Harold, put a damper on her plan to buy a new car by revealing they have money problems like her.
Ellen thinks that Holly's new boyfriend, Steve, is hitting on her. But Holly, along with everyone else, refuses to believe Ellen's suspicions. Determined to get hard evidence, Ellen plans a microphone on her and tries to get Steve to make a pass at her, but it turns into Ellen having to come onto him which her plans fall apart. Meanwhile, things change at the bookstore when Susan hires "Coffee" Joe Farrell to manage the new coffee shop and he and Ellen don't seem to hit it off.
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.