Fans can argue that compared to other pairings between the six friends, Chandler and Rachel had only a handful of memorable interactions and storylines together, such the one where Chandler has a relationship with Rachel’s boss Joanna and finds himself handcuffed in her office, begging Rachel to help him out. Rachel often admits that out of the three male friends, Chandler is the one that she likes the least. When Joey casually asks her who she’d like to punch among the friends, Chandler’s name pops up in her mind. When given a choice between kissing Joey and Chandler at a New Year’s party, she instinctively rejects Chandler.
The pilot episode of “Friends” makes it seem like it’s the first time Rachel meets Chandler, and the only two friends she’s met previously are Monica and Ross. Rachel evens remarks that she thought Chandler was gay until an incident involving breasts at Phoebe’s birthday party indicates otherwise.
But there are several instances shown where the two had met long before their supposed introductions at Central Perk. In the Thanksgiving flashback episodes, Chandler visits Ross’ parents’ home for the holiday where Monica’s best friend Rachel is also present. She helps Monica scheme her revenge against Chandler a year after he calls Monica “fat.” At a college party that Rachel and Monica sneak into, Chandler kisses Rachel as an act of revenge against Ross after Ross breaks their agreement to not pursue a girl they both like. In a separate incident, the two cross paths again exactly a year before the events of the pilot episode, where Rachel visits the bar (which later turns to Central Perk) that Monica and Chandler frequent. While it’s made to look as though Chandler and Rachel are about to hook up, they’ve somehow forgotten each other, again, by the time of Episode 1.