What was the most awkward moment between the female characters on Friends?

There were many memorable and often hilarious moments between the female characters on Friends, but one of the most awkward was in the episode 'The One with the Embryos' in season 4. In this episode, Rachel and Monica compete against Chandler and Joey in a trivia game to determine which pair knows the other better.

During the game, one of the questions is about a particular book that Chandler's mom gave him to read when he was younger. After some back-and-forth, Chandler reveals that the book is called 'The Velveteen Rabbit,' but Rachel and Monica incorrectly guess 'The Shining.' This leads to an argument between the two pairs, which culminates in a high-stakes game of 'who knows who better.'

While the awkwardness of this moment is played for laughs, it also underscores the deep friendships and rivalries between the female characters on the show. Despite their disagreements and occasional awkward moments, Rachel, Monica, and Phoebe remained close throughout the show's 10-season run, providing some of the most iconic and memorable moments in television history.