The episode starts with Monica telling Chandler she got new boots which she absolutely loves however they are extremely expensive and Chandler wants her to return them.
Rachel, Phoebe and Joey are in Central Perk. As Rachel goes to leave she meets Joey who asks her whether she can speak to his younger sister Dina, who is inspired by Rachel's work. Phoebe finds out that Ben and Sting's son go to the same school. Phoebe is ecstatic and thinks she may be able to use the situation for her advantage, she wants to go to Sting's concert but the tickets are sold out so she plans to meet him personally.
Monica enters Central Perk and Rachel starts to compliment her saying how nice the boots are. Monica however says she doesn't like them at all; they are incredibly painful to wear, but Chandler can't find out. Ross enters and tells Phoebe he won't be able to get the tickets because Ben and Sting's son don't get along. Phoebe wants Ross to try to get the two children to be friends so she can get the tickets.
Joey introduces Dina to Rachel at her work place. As soon as Joey leaves, Dina reveals she doesn't care about the work Rachel does she just wants her help because she is pregnant herself.
Monica enters her apartment and Chandler tells her his office holiday party is that evening and that Monica can wear her boots. Monica tries to find various excuses not to wear the boots though but in the end she is going to have to wear the boots to the party.
Dina tells Rachel that she is hesitant about telling Joey that she is pregnant, Rachel tells her Joey will be supportive. They enter his apartment and Dina tells Joey she is pregnant, Joey however doesn't take it very well saying she has always been the clever one.
Phoebe enters Ben's school to meet Ben and try to solve the problems between Ben and Jack (Sting's son). Phoebe meets a tutor and has to pretend that she is one of Ben's lesbian moms in a hope to meet Sting.
Monica and Chandler are walking out of the party where Monica confesses that the boots were a wrong idea and that Chandler was right.
Dina and Rachel are talking about pregnancy when Joey storms into the room manhandling Bobby (who got Dina pregnant). Joey tries to marry the two saying it's the only right thing however everyone else thinks what he is doing is wrong.
Phoebe is at Sting's house having a conversation with Jack's mom. She tells Phoebe that Sting won't be joining them. Phoebe tries to reschedule at a time when Sting is available and soon Sting's wife catches on and Phoebe has to leave with no tickets.
Chandler is giving Monica a piggyback ride when they realize they left behind her boots they settle that she won't wear them anyway.
Back at Joey's apartment, Joey insists Bobby and Dina get married if Dina has a baby. He says if she doesn't she will be ruining her life. Rachel objects saying she is in a similar position and she hasn't messed up her life but Joey tries to explain how it is different. The matter is resolved and Joey says he will always be there for her.
At Central Perk Ross reveals that he managed to get tickets to see Sting.