At the Central Perk coffee shop, Monica's friends playfully make fun of her for going out with someone and saying it's not a date. Ross, Monica's older brother, comes in looking depressed because his ex-wife, who is now in a relationship with her lesbian partner, has moved out of their apartment. Suddenly, a young woman wearing a wet wedding dress arrives, and Monica recognizes her as her best friend from high school, Rachel Green. Monica introduces Rachel to everyone, and Rachel explains that she left her fiancé at the altar because she realized she didn't love him. When Rachel's father cuts off her money over the phone, Monica reluctantly offers to let Rachel stay with her as a new roommate.

Meanwhile, at Ross’s apartment, Joey and Chandler comfort Ross about the loss of his wife. They help him put together new furniture. Ross starts to wonder if he'll ever find the right woman for him. Monica goes on her first date with a guy named Paul, known as "the wine guy," who tells her that he's been having trouble with his sexual performance since his wife left him. Monica is touched by his honesty, and they end up sleeping together. However, the next day, Monica learns from a coworker that Paul's story about his ex-wife is a trick he uses to pick up women.

Rachel, struggling to find a job, ends up using one of her credit cards, which her father pays for, to buy a new pair of boots. She reluctantly admits this to her new friends, and with their encouragement, she decides to take a big step towards independence by cutting up her credit cards.

Later that night, Ross and Rachel have a heart-to-heart talk. Ross confesses that he had a crush on Rachel during high school, and she admits that she knew about it. Ross asks if he can take her out on a date sometime, and she happily agrees. Ross leaves Monica's apartment with newfound hope.