Ep 19. The One Where Ross Can't Flirt

The One Where Ross Can't Flirt is the nineteenth episode of the fifth season of the popular sitcom Friends. The episode centers around Ross's struggle with flirting, prompting his friends to intervene and offer him advice.

The episode opens with Ross arriving at Monica's apartment with news of his new crush, a pizza delivery girl named Caitlin. However, when Caitlin arrives to deliver pizza, Ross becomes incredibly awkward and unable to flirt. His friends notice his discomfort and try to help him, with Joey offering to coach him in the art of seduction.

Meanwhile, Chandler is struggling with the fact that he can't tell if a co-worker named Wendy is flirting with him or just being friendly. He seeks advice from Monica, who suggests that Wendy may be interested in him.

Back at Monica's apartment, Joey attempts to teach Ross the "Joey Tribbiani method" of flirting, but Ross is still unable to master the technique. Rachel suggests that Ross try a different approach and be himself, but this only causes Ross to become even more nervous and awkward around Caitlin.

Later, while at Central Perk, Ross runs into Caitlin again and attempts to ask her out on a date. However, he once again becomes tongue-tied and ends up accidentally inviting her to his grandmother's funeral instead. Embarrassed, Ross retreats to the safety of his apartment.

After talking with his friends, Ross realizes that he has been putting too much pressure on himself to be a good flirt and decides to simply be himself around Caitlin. When he sees her again, he is calm and confident and finally succeeds in asking her out on a date.

Meanwhile, Chandler comes to the realization that Wendy is only being friendly and not actually interested in him. He is disappointed but ultimately decides to move on and focus on other aspects of his life.

The episode ends with Ross excitedly telling his friends about his successful date with Caitlin and Chandler jokingly attempting to use Joey's flirting tips on Monica.

Overall, The One Where Ross Can't Flirt is a humorous and relatable episode that explores the struggles of dating and flirting. It showcases the strong bonds between the characters and their willingness to help each other through difficult situations.