15 Saddest How I Met Your Mother Episodes
9. Come On (Season 1, Episode 22)
In many ways, Come On features one of Ted's best moments. Trying to stop Robin going on a trip with her creepy co-anchor Sandy Rivers, Ted enlists the help of Barney and Barney's ex Penelope to perform a "rain dance," in hopes of seeing the trip cancelled. The rain dance "works" and the get-away is put on hold, giving Ted the boost needed to go after her one last time.
But whilst the future couple finally decide to give their relationship a shot, Marshall and Lily find themselves in a fight about Lily's desire to go to an art fellowship in San Francisco. Believing she needs time away from their relationship to really find herself, Lily leaves Marshall... and her engagement ring.
Ted, oblivious to this, returns to the apartment having had one of the best nights of his life, only to find Marshall sitting on the stairs, drenched by the rain, holding Lily's ring. A shock twist, seeing Marshall sitting there soaked through is a real heartbreaker.