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

4. Zoey Pierson (Played By Jennifer Morrison)

Oh, the lengths Ted Mosby will go to in order to woo a lady.

When Ted met Zoey in front of the Arcadian building, he agreed to join in the fight to prevent the hotel from being torn down. Ted failed to mention that he was the architect of GNB’s new headquarters, the very building that would replace the dilapidated, snake infested- I don’t recall saying snake infested- hotel. When Zoey found out he was a GNB employee and Ted found out she was married, their relationship shifted from allies to enemies. During an emotional Thanksgiving, Zoey and Ted were able to put their differences aside and become friends.

Despite becoming a corporate employee of GNB, Ted continued to see himself as both free spirited and anti-establishment. Being a tenacious grassroots activist who ardently fought against injustice was exactly what charmed Ted about Zoey. While he attempted to distance himself from Zoey to avoid any impropriety or heartbreak, upon learning of Zoey’s divorce, the two immediately begin a romantic relationship.

This relationship was only every going to be temporary; they were at odds on most issues and Zoey’s attempts to save The Arcadian were in direct conflict with Ted’s professional ambitions. While it was doomed from the beginning, it was inspiring to see two individuals, whose opinions often differed, were still able to fall in love. Zoey’s introduction also gave HIMYM fans one of the greatest secondary characters in the show’s history: The Captain.