While hiring a new assistant, Rachel is torn between hiring a much more qualified woman, or a handsome but inexperienced young man. Monica, Chandler and Ross engage in a war of secret sharing after Monica and Chandler vow to be more honest. Meanwhile, Joey has problems when his TV show is cancelled after just one airing.

While taking an engagement picture for himself and Monica, Chandler cannot make anything but a weird face. Meanwhile, Rachel enlists Joey to take Tag out for a night on the town. Also, Phoebe and Ross date a couple in the middle of a divorce.

Ross drives himself insane when he can't name all 50 states in a simple game. Tag joins the gang for Thanksgiving dinner, where Joey accidentally spills the beans about Rachel's crush on him. Phoebe sneaks a dog into the apartment, making Chandler extremely nervous.

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.

After the gang head up to the roof to see a passing comet, separate events unfold that lead to them all having a sleepless night.

When Rachel turns 30, the gang reminisces about their 30th birthdays. Ross buys a sports car to look cool, Monica gets drunk, and Phoebe, while trying to patch things up with Ursula, discovers that she is actually 31.

Speculation regarding the father of Rachel's baby leads to a misunderstanding when Joey discovers a red sweater left behind in a one-night stand Rachel had. Meanwhile, Chandler and Ross search for the disposable cameras left behind at the wedding and Monica goes on a present-opening binge.