#15: When he was trying to propose (Season 6, Episodes 24–25)
Chandler’s attempt to propose to Monica Geller turns into a carefully planned emotional journey filled with misdirection and vulnerability. Determined to surprise her, he initially pretends to be against the idea of marriage altogether. This deliberate act creates confusion and even doubt, as Monica begins to question their future. Meanwhile, Chandler struggles internally, balancing his fear of commitment with his deep love for her. The tension builds as misunderstandings escalate, especially with the reappearance of Richard Burke. When the truth is finally revealed, the moment becomes deeply emotional.

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