How I Met Your Mother: Ranking All Of Ted Mosby’s Serious Relationships From Worst To Best

6. Stella Zinman (Played By Sarah Chalke)

Stella was the first woman Ted romantically pursued, in any serious way, following his break-up with Robin. Throughout his tattoo removal sessions, both were flirtatious and when finally given two minutes of her time- quite literally- Ted put together a thoughtful date which resulted in him turning Stella’s no into a yes.

Upon getting engaged to Stella, Marshall was the voice of reason, telling Ted that they didn’t know each other well enough to get married. This foreshadowing was brilliant as Ted’s wedding ultimately ends in disaster. Everyone is entitled their secrets, but for Stella to withhold the fact that she was in love with her ex, Tony, whom she had a child with and believed to be ‘the one’ for her- that is some pertinent information to be keeping from her fiancée.

Initially, Stella seemed like a great match for Ted, being a family oriented, fun-loving person. As the curtain was pulled back, however, it became clear that she was not only in love with Tony, but, at the very least, she was apathetic towards Ted’s feelings. Following their split, Stella sought out Ted’s help in trying to win Tony back, when he briefly ended things with her. She also had no problems with Tony’s blockbuster movie The Wedding Bride, which could not have painted Ted in a worse light.

Stella was the nastiest heartbreak of Ted’s life, although it wound up being fortunate he was left at the altar, as she was also Ted’s cruellest partner.