Friends: 10 Most Heartbreaking Episodes
9. The One With The Boob Job (S9, Ep 16)
While the episode's title might not evoke any tragic feelings, it's yet again Phoebe's storyline that puts this entry on the list.
Eight years on from her encounter with David, Phoebe finds proper love with Mike (because who doesn't love Paul Rudd?) and realises that he's the man she wants to finally settle down with and marry. Unfortunately, Mike doesn't want to tie the knot due to his last marriage.
What's emotionally frustrating (but very realistic) about this episode is the mental challenges Phoebe goes through to try and stay with Mike, before she finally admits to herself that, if he doesn't want to get married, he's probably not the one for her.
We get a great insight into her psyche during this episode, and it culminates in another realistic scene where neither of the pair refuses to back down from their respective stances, and so decide to call time on their relationship.
While we were all relieved to see them reunite in the end, Phoebe and Mike's relationship wasn't without its struggles, as this episode proves. And of course, we all felt for the main guys who then had to move Mike's stuff back down the stairs...