15 Saddest How I Met Your Mother Episodes
11. Shelter Island (Season 4, Episode 5)
For all his personal faults, Ted is a guy who went through an awful lot before he met the Mother. Few things are as tragic and hard-hitting, though, as the moment he realises that Stella has left him at the altar, running off with her ex at the last minute and leaving a letter to explain her actions.
Shelter Island has got plenty of funny moments, from Barney's attempts to not sleep with anyone before Robin arrives and the gang's realisation that the wedding venue is an alcohol-free, vegan-friendly establishment, but all of the humour is undercut by that final image.
With Benji Hughes' "Waiting For an Invitation" playing over the action, Ted reads Stella's letter and is consoled by Marshall, Lily and Barney, whilst Robin sees Stella and her ex sailing off the island together. It's one of the worst things to ever happen to poor ol' Ted, and whether you love him or hate him, in that moment it's impossible not to just want to give him a hug.