2x14 "The One with the Prom Video"

After getting his big break with Days of Our Lives, Joey pays Chandler back with $812 and an extremely tacky engraved gold bracelet. Also, an unemployed Monica is hard up for money. A home video from Monica and Rachel's prom night reveals that Monica was previously overweight, and that Rachel had a large nose. Rachel seemed to have been stood up by her prom date, so Ross puts on his father's tuxedo to take her to prom himself, but Rachel's date shows up and they leave before she learns of Ross's plans. The video then shows a speechless and devastated Ross standing at the top of the stairs. The candor of Ross's heartbreak compels Rachel to kiss Ross.