15 Saddest How I Met Your Mother Episodes

In what is most likely Ted's worst episode, Nothing Good Happens After 2 A.M. sees him going round Robin's apartment late at night, despite still being in a long-distance relationship with Victoria. Though he has an opportunity to tell Robin he and Victoria are still together despite his worries she wants to break up with him, he lies and says they've split up.

By this point in the show's first season, after a maddeningly long will-they-won't-they stint, Robin has finally realised she has feelings for Ted, and takes the chance to tell him how she feels about him. They kiss, only for Ted to realise he needs to actually break up with Victoria before making it work with Robin.

Unfortunately, his ill-formed plan hits a snag when Robin answers his phone and finds out that he and Victoria are still together. Robin kicks him out the apartment, Victoria breaks up with him, and with his worst-ever decision, he loses both women in one night.