15 Saddest How I Met Your Mother Episodes
3. The Time Travelers (Season 8, Episode 20)
How I Met Your Mother loves a good twist, and whilst The Time Travelers is, for the most part, a pretty standard slice of sitcom joy, things escalate into tragedy rather quickly. The episode sees Ted and Barney at the bar, talking to future versions of themselves about what would happen if Ted went to Robots vs Wrestlers. A sub-plot also sees Marshall and Robin fighting over who came up with a new drink on the menu.
Pretty standard stuff, but everything hits a bump when Ted sees a woman from his past and contemplates talking to her, only to realise there's probably no point, because all his relationships end the same way. Then, adding insult to injury, Barney reveals that Ted's hallucinating everything; he's alone, at the bar, whilst his friends move on with the lives he himself has always wanted.
Leaving the bar, Future Ted admits he wishes he could go back in time and talk to their mother that night, in order to let his past self know that everything would be okay in the end. It's a gut-punch of a reveal which really comes out of nowhere, and Ted's final speech is nothing short of soul-crushing.