15 Saddest How I Met Your Mother Episodes
8. A Change Of Heart (Season 6, Episode 18)
With season six came a new, more mature side to Barney Stinson. He starts dating Nora, only to find himself caught between his true feelings about the future and his usual attitude to love. He spends their date lying about how he wants the same things from life as her, but in the end comes clean and says he was only acting that way to make her like him.
Nora is fairly mortified and leaves. Later, though, Barney realises he does in fact want all those things they were talking about, and makes the bold decision to go after her whilst she meets with her parents.
The final scene shows him admitting how confused he is about his feelings and hitting it off with Nora's parents, only for a tragic reveal to show that he's been imaging the whole thing. Watching Nora and her parents, Barney loses the courage to confront her, and walks off with tears in his eyes. Always the funny playboy, this moment still stands as one of Barney's saddest moments.