Friends: 10 Most Heartbreaking Episodes
1. The One With The Prom Video (S2, Ep 14)
Yes, it's a predictable number one spot, but it really did have everyone grabbing the tissues.
The One With The Prom Video is a strange episode really - sure, it's got the happy ending we were all hoping for (a full season before that awful break-up), but the core of the episode is really about exploring Ross's backstory, his vulnerabilities as a person and the insecurities he feels in his love life. Not everyone's a fan of his character at times (especially in later seasons) but here he's shown as quite naïve and insecure.
You can't help but feel for him when Rachel harshly shoots him down at the start of the episode, despite his previous mistakes, and then when we get to the prom video itself, you can clearly see the fear on his face as his friends discover what he tried to do for Rachel as a teenager, clearly terrified of their reaction. David Schwimmer acts his socks off again here and you can really feel how that moment affected Ross's self-esteem throughout his life.
It did get the happy ending that both Ross and Rachel deserved, but it took a lot of challenges to get there.