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.