7. The One with the Proposal (Season 6, Episodes 24 and Episode 25)
Sadly, Matthew Perry struggles to play an emotional wreck. Sarcastic, smug and childish is Chandler. Romantic, crying and angry isn’t exactly his thing. Despite this, The One with the Proposal forced him to step up to the plate. It’s not as upsetting as some episodes higher in the list but the use of Richard (Tom Selleck) and suddenly-serious approach to Chandler’s lack of commitment make the situation heart-breaking. Joey, telling Chandler that Monica has left is the icing on the cake. Courtney Cox has always managed to play Monica with real heart, and her intense, controlling nature does mean that Monica proposing to Chandler equally makes sense. But, seriously, there are way too many candles. How long did it take to set that up? Isn’t that a huge safety risk? Mr Treeger wouldn’t be amused at all.
