Friends: 10 Most Cringeworthy Moments
3. Chandler & Phoebe
The sneaking around in the early days of Chandler and Monica made for some great moments of suspenseful humour, and Joey's gradual breakdown over trying to keep their secret is a memorable feature of Season 5, but the biggest cringe came as part of a game of chicken as Phoebe "seduces" Chandler.
Phoebe and Ross become the final Friends to find out about the relationship. The girls, angered by Monica keeping this a secret from them, set about making life difficult for the pair until they are forced to reveal the truth.
Eventually this leads to Phoebe's fake attempted seduction, and Chandler being egged on by Monica to play along, ostensibly to keep up the charade, but it has to be noted at this point, it probably had more to do with Monica's competitive streak and fixation on "winning" the situation. The tension is ramped up with wine, dancing and lotion, before Chandler eventually freaks out after a brief kiss.
With the coupling up of Joey and Rachel largely considered a black mark against latter season Friends, we are all pleased to see this particular tryst was left as a one-off joke.