Friends: 10 Most Heartbreaking Episodes

5. The One Where Chandler Crosses The Line (S4, Ep 7)

Friends Rachel
NBC

This one really stung for anyone who's in a bromance out there.

Joey and Chandler were the lovable pair of flatmates who had never really argued over a serious matter up until this point. In fact, they were normally the ones trying to stop the others fighting in the first few seasons.

And so it was a really tragic situation to see Joey's girlfriend Kathy come between the pair. Chandler, normally terrified of women, finds himself falling for Kathy and believes the two would make a better couple than her and Joey. Despite trying not to hurt his friend, he ends up kissing Kathy in a heart-wrenching moment for the show, before an even more painful scene ensues when he comes clean to Joey in a bid to do the right thing.

There's a real mixture of emotions and conflicting opinions in this episode. For some, Joey probably comes off as the bad guy - he doesn't take Kathy too seriously and refuses to understand his friend's feelings. On the other hand, Chandler is the one who betrayed his best friend's trust, and the end of the episode leaves a bitter taste in the mouth as the two pals go through their first major bust-up.

Because, let's be honest, they really were the best couple on the show.

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Jamie is a freelance broadcast journalist and writer, with a particular obsession for sci-fi, theatre and politics. In his spare time he enjoys amateur dramatics and making homemade curries.