Barry and Mindy's impending divorce prompts the gang to fantasize about what their lives might be like if they'd all taken different courses. Ross is still married to Carol, and Rachel is married to Barry, but fawning over famous soap star Joey Tribbiani. Monica is still fat and dating a doctor. Chandler is an aspiring writer and Phoebe is a Wall Street shark for Merrill Lynch.

The gang continue to fantasize about how different their lives could have been. Carol and Ross decide to have a threesome to spice up their marriage. Rachel goes to Joey's but is incredibly nervous about cheating and gets drunk. Meanwhile, Monica's dinner date falls through and Chandler tries to cheer her up but things take an unexpected turn.

When Phoebe tells the gang about how she was too poor to have a bike as a child, Ross goes out and buys her one. While Phoebe absolutely loves the bike, the gang soon discovers that she doesn't actually know how to ride one. Meanwhile, Monica decides to make candy in order to get to know her neighbours, and while they all love the candy, nobody is particularly interested in Monica herself. Rachel and Tag try to hide their relationship at work, but things go awry when Rachel writes a playful work evaluation of Tag that he accidentally turns in to Human Resources.

Ross's plans to teach Ben about Hanukkah are continually thwarted when the young boy can't get his mind off of Santa. Meanwhile, Phoebe prepares to move back into her refurbished apartment, with or without Rachel. However, she'll stop at nothing to get Rachel to go with her, including buying Joey a drum set. Monica is mystified by Chandler's inability to tip properly.

Chandler is shocked to find out who Monica really wanted to sleep with the night they first got together in London. Meanwhile, Rachel gets into trouble with Ross when she teaches Ben practical jokes.

The excitement of Monica and Chandler's wedding is diminished by the news that someone may be pregnant. Chandler's hopes of not embarrassing Monica on the dance floor are ruined by his slippery new shoes, and Ross' attempts to flirt with an attractive wedding guest.

Chandler is peeved when Monica splurges on an expensive pair of boots. Meanwhile, Phoebe learns that Ben and Sting's son attend the same school and she angles to meet the celebrity and get concert tickets. Also, after Joey's sister Dina tells him that she's pregnant, he freaks out and goes to find the father to marry them. Rachel tries to calm him down.

Phoebe gets Monica and Chandler a Ms. Pacman arcade game for a wedding present, which leads to some heavy competition between Monica, Phoebe, and, surprisingly, Chandler. Ross gets to teach an advanced class because of a retiring professor, but soon learns that its on the other side of town, and he doesn't have enough time to get there. Meanwhile, Joey takes Rachel to dinner on a pretend date and they have a great time together, however, at the end of the night things take an unexpected turn.