After almost eight full seasons, HIMYM’s star character Ted Mosby (Josh Radnor) has had more than his fair share of relationships. Some may not have lasted long (think Blah Blah or Honey), but others seemed like they held great potential and could have fit into the role of the yet-to-be-seen mother.
Ted has had roughly 30 potentials over the last 7 1/2 seasons, five of which could be considered ‘serious’ relationships. Serious or not, there is no doubt that all loyal HIMYM viewers have their favorite Ted Mosby romance. From the brief cameos of Katy Perry as Honey and Mandy Moore as Amy, to the more long-term roles of Stella and Victoria, each of Ted’s exes are memorable and awesome in their own way.
Here is a list of some of Ted’s greatest and most memorable romances, although everyone can probably agree that all 30 are pretty legendary.
Season one’s Natalie, played by Anne Dudek, is most memorable for her violent reaction to Ted dumping her on her birthday…twice. In Return of the Shirt, she reluctantly rekindles her old flame with Ted, after he broke her heart three years prior via answering machine, on her birthday. When he ends up breaking it off again, this time in person, she uses her skills in Krav Maga to show him once and for all birthdays are not an appropriate day to end a relationship.
Mary the Paralegal
Also from season one is Mary the Paralegal, played by Erinn Bartlett. Poor Mary is set up with Ted on a blind date, by Barney who lies and tells Ted she is a prostitute. Despite what Ted believes she does for a living, he ends up genuinely liking her. Unfortunately neither Ted nor Mary know of Barney’s lie, so when Ted calls her out on being a hooker, she slaps him and leaves him on his own.
Abigail Spencer, affectionately known as Blah Blah in season three, is the character that allows Barney’s introduction of the Hot/Crazy Scale. Having met her online playing World of Warcraft (not in a cooking class), Ted has no idea what he is in for when he meets Blah Blah in person. Once she finds out that Ted and Robin dated, she becomes increasingly insecure and neurotic until she storms off in a rant about wanting to see her name up in lights.
Vicky comes into the picture in season four’s The Naked Man. After being left at the altar, Ted meets Vicky in an elevator and works up the courage to ask her out. After realizing that she is not exactly the kind of person he wants to spend his life, or even one more date, with, he decides to try “The Naked Man” to get her into bed. It works gangbusters, and she serves her character’s purpose of getting him back into the swing of things after having such a broken heart.
Ted dates Royce in season five, and he really likes her for the first couple of weeks. After searching for her “baggage” and not finding any, Ted takes her to see a new movie titled The Wedding Bride where he realizes he has quite a bit of baggage himself. After pouring his heart out in front of a crowded theater, he and Royce have a real heart-to-heart, where she reveals that she has been left at the altar three times, she has a gambling addiction and she lives (and shares a bed with) her brother. Having finally discovered her baggage, and realizing that his pales in comparison, he promptly tells her that she’s “gotta go.”
Karen (Laura Prepon) is Ted’s first real relationship. She was his college girlfriend, off and on, and was always hated by Marshall and Lily. When she resurfaces in season four, Ted falls in love with her again immediately and Lily is forced to try to break them up. Of course her plan backfires at first, but once Karen tells Ted he can’t see Lily anymore, he promptly picks his friends over his girlfriend and Karen is gone for good.
While Cindy isn’t around for long in season five, she pays a key role in the progression of the show. We learn that Cindy is actually roommates with Ted’s future wife, and while we don’t see her face, Ted finds multiple things in their apartment that show some true insight into the mother’s character. Cindy has a “roommate complex” and despite Ted promising her that he will not fall in love with her roommate he just can’t help it. It’s okay, though, because we later learn that Cindy is actually a lesbian and the relationship never would have worked anyway.
Love her or hate her, Zoey (Jennifer Morrison) was in Ted’s life for some time in season six. Their relationship was full of turmoil, starting off as arch-enemies fighting over the future of a historical building. They become friends, and Ted begins falling for her even though she is married to The Captain. She falls for Ted soon enough, ending her marriage to be with him. Eventually, though, the constant fighting and tension over the beautiful Arcadian proves to be too much for the couple, and they split.
Victoria, played by Ashley Williams, is one of Ted’s most serious and memorable girlfriends. In season one, Ted meets her at Stuart and Claudia’s wedding and they fall for each other immediately. Everything is perfect until she gets a huge opportunity in Germany, and despite Ted’s best efforts, a long-distance relationship is too difficult after only two months together. They split until she resurfaces in season seven, and she and Ted give the relationship another shot. It seems like they may be destined to be together, until she lets her jealousy of Robin get in the way and they end their relationship once and for all in season eight.
Ah, Stella. The one that got away. Stella Zinman (Sarah Chalke) is Ted’s most notable ex. He puts forth an enormous amount of effort trying to turn her “no” into a “yes” in season three, and once he succeeds, the relationship moves quickly. After a brief breakup, Ted proposes and they make plans for him to move to New Jersey with her and her daughter, Lucy. The wedding comes sooner than Ted expects, and after inviting Stella’s ex, Tony (Jason Jones), to attend, Stella leaves Ted at the altar with only a note explaining why. Stella resurfaces multiple times, and Tony not only gets him his job as a professor, but also becomes the director of The Wedding Bride, a movie based on Ted and Stella’s entire relationship.