Friends: Every Season Finale Ranked Worst To Best
2. The One With The Proposal (Season Six)
Chandler and Monica's wedding was an exceptional season finale, but it was outmatched by their engagement in the prior season's finale.
Again going down as a two-parter, Chandler's initial proposal at a restaurant is thrown off by the arrival of Richard, who later announces he's still in love with her, unbeknownst to Chandler. Monica is left confused, with Chandler admitting he doesn't see the point in marriage, Joey telling her he means the opposite, and Richard, too, wanting to marry her.
It all concludes with Chandler and Monica becoming engaged, but only after Joey fooled the former into believing Monica had abandoned him due to his commitment issues. Instead, he entered their apartment to find it covered in lit candles, Monica standing across from him.
This was peak drama from Friends. Matt LeBlanc acted with conviction here; he sounded real when telling Chandler the unfortunate news of Monica leaving him. This only added to the whole scenario, with both Matthew Perry and Courtney Cox also performing superlatively while proposing.
The subplot of Joey, Rachel, and Phoebe participating in a silent auction, the entire premise of which is misunderstood by Joey as he bids $20,000 on a boat, is an often overlooked, yet hilarious aspect of this finale. It was needed to enhance the drama of the main story being told.