10 Friends Timeline Mistakes You Never Noticed

Ross' petulance with hastily fast-forwarding relationships is universally as eminent a piece of Friends lore as Chandler's crying impotence.

The backstory was the key plot of season six's fourteenth episode The One Where Chandler Can't Cry, where Monica, Joey, and Phoebe badger Chandler until, eventually, he does finally shed some tears, caused by Ross and Rachel being unable to work out their relationship. Having had his "crying gate opened", Chandler cried again during the episode's credits when Rachel's sister Jill (Reese Witherspoon) storms out of the coffee house.

Although this appears to be a tied-up piece of Friends lore, given how salty and disparaging he often comes across, Chandler has cried on a scattering of occasions, including twice in the fourth season alone. He sobbed in the fourteenth episode The One With Joey's Dirty Day after Phoebe yelled at him for languishing the end of his relationship with Kathy (Paget Brewster), and then in the twenty-second episode The One With The Worst Best Man Ever, where Ross profoundly and emotionally expresses his eagerness for both Chandler and Joey to be his best man.

It's not a vital plot point, but ostensibly the writers implemented the crying impotence storyline as a means of balancing Chandler's leading characteristics so that the typically sarcastic character can, when it's needed for the episode, display empathy and affection without overstepping the mark.