Ted Mosby’s 10 Most Important Girlfriends: Re-Evaluating The Hopeless Romantic And The Controversial HIMYM Ending In 2025

Theodore "Ted" Evelyn Mosby, the protagonist of the beloved sitcom *How I Met Your Mother* (*HIMYM*), remains one of television's most debated characters, even in late 2025. His decade-long quest for "The One" defined a generation of romantic comedy, yet his journey—and the controversial final twist—still sparks heated arguments among fans and critics alike. As we look back at the show's legacy today, December 15, 2025, the central question shifts from "Who is The Mother?" to a more profound one: Was Ted Mosby truly a hopeless romantic, or was he a character whose idealism masked a deep-seated inability to move on from his first great love, Robin Scherbatsky? The answer lies in the complex web of relationships he navigated, each one a stepping stone toward—and sometimes away from—his destiny with Tracy McConnell.

Theodore Evelyn Mosby: The Architect's Profile

The story of *How I Met Your Mother* is framed by Ted Mosby (played by Josh Radnor) recounting his younger life to his children, Penny and Luke, in 2030. His narrative is the foundation of the entire series, painting him as an idealistic architect from the Midwest.

• Full Name: Theodore Evelyn Mosby
• Born: April 25, 1978
• Hometown: Shaker Heights, Ohio
• Occupation: Architect, later Architecture Professor at Columbia University
• Core Group: Marshall Eriksen (best friend), Lily Aldrin (Marshall's wife), Barney Stinson (best friend), and Robin Scherbatsky (on-again, off-again love interest)
• Spouse: Tracy McConnell (The Mother)
• Children: Penny Mosby and Luke Mosby
• Defining Object: The Blue French Horn

Ranking Ted Mosby’s 10 Most Significant Girlfriends

Ted Mosby dated an estimated 30 women over the course of the series, but only a handful truly shaped his character arc and the ultimate narrative of the show. These relationships weren't just filler; they were essential lessons in what he wanted, what he needed, and why he couldn't have Robin.

1. Tracy McConnell (The Mother): The undisputed number one. Tracy was Ted's true match, sharing his love for history, correcting his mistakes, and offering the effortless, grown-up love he spent a decade searching for. Their meeting under the yellow umbrella was the payoff for the entire series, and their relationship, though tragically cut short by her death, was "The One."
2. Robin Scherbatsky: The first love and the ultimate endgame, despite the controversial ending. Robin was the love Ted needed to let go of to become the man who could meet Tracy, but she was also the person he returned to after Tracy's passing. Their relationship, marked by the iconic blue French horn, was a constant, tumultuous force.
3. Victoria: The baker who got away—twice. Victoria was arguably the closest Ted came to "The One" before Tracy. She represented a classic, fairytale romance and was a significant lesson in timing and commitment.
4. Stella Zinman: The one who left him at the altar. Stella taught Ted a painful, unforgettable lesson about rushing into commitment and the compromises required in a blended family. Her arc was a pivotal moment of growth for Ted.
5. Zoey Pierson: The passionate, yet ultimately incompatible, activist. Zoey was a foil to Ted's career ambitions, particularly his GNB headquarters project. She showed him that even intense chemistry isn't enough to overcome fundamental differences in life goals.
6. Jeanette Peterson: The chaotic, obsessive, and ultimately destructive relationship. Jeanette represented Ted's rock-bottom in dating, a sign of his desperation to find *anyone* to be "The One".
7. Karen: The snobbish, pretentious college girlfriend. Karen was a recurring mistake who highlighted Ted's insecurity and his tendency to seek approval.
8. Naomi (The Slutty Pumpkin): A perfect example of Ted's over-idealization of women. The decade-long pursuit of "The Slutty Pumpkin" showed how Ted often fell in love with the idea of a person rather than the person themselves.
9. Cindy: Tracy's roommate. Cindy was important because she was the first character to directly connect Ted to Tracy's world, famously owning the yellow umbrella.
10. Trudy (The Girl in the Red Boots): A minor character, but she introduced the concept of the "re-return," one of Ted’s many romantic theories, adding to the show's mythology.

The Enduring Debate: Was Ted Mosby a Hopeless Romantic or a Jerk?

The character of Ted Mosby is constantly re-evaluated by modern audiences, leading to a polarizing debate: Is he the sweet, idealistic hero, or a self-centered, over-romanticizing "villain"?

The Argument for "Hopeless Romantic"

For most of the series, Ted is portrayed as the ultimate romantic—the man who would steal a blue French horn, wear red cowboy boots, and travel across the country for a girl. This idealism is the core appeal of the show. His desire for a deep, meaningful love is relatable, and his eventual relationship with Tracy McConnell validates his decade of searching. He is the glue of the group, a loyal friend, and a man who genuinely believes in destiny and grand gestures.

The Argument for "The Jerk/Villain"

Recent analyses, including a 2025 retrospective, often point out Ted's more problematic behaviors. Critics argue that he often put his own romantic needs above the feelings of his girlfriends and friends. For example, he constantly sabotaged his relationships by comparing every woman to Robin. His decision to date Jeanette, a woman clearly unstable, and his obsessive, stalker-like tendencies (like showing up at Robin's apartment unannounced) are often cited as evidence that his "romanticism" was actually a form of self-sabotage and immaturity. The writers even acknowledged that they purposefully made Ted a "jerk" in early episodes to show his flaws.

The Controversial Ending and the Alternate Reality

The series finale, which aired in 2014, remains one of the most divisive conclusions in sitcom history. In the final moments, Tracy McConnell (The Mother) is revealed to have died six years before Ted tells his story to his children in 2030, and the entire narrative was a pretext to get his children's permission to date Robin Scherbatsky again. The controversy was immediate and intense. Fans felt the entire final season, which was dedicated to Barney and Robin's wedding and Ted finally meeting Tracy, was rendered meaningless. The death of Tracy, the character everyone spent nine years waiting for, felt like a cheap plot device to facilitate the reunion of Ted and Robin.

The Alternate Ending Perspective

The backlash was so significant that the creators released an alternate ending on the DVD box set. In this version, Tracy does not die. Ted finishes his story, and the final scene is simply Ted and Tracy meeting at the train station under the yellow umbrella, confirming that she was "The One" and that their love story was the true focus. This alternate ending is often preferred by fans because it honors Ted's journey and Tracy's character arc. However, the co-creator, Craig Thomas, defended the original ending, stating it was an "exploration of life" and how things don't always work out perfectly. Ultimately, the debate over the ending is an exploration of two different realities: the idealistic fairytale (the alternate ending) and the messy, complicated reality of life, loss, and second chances (the original ending). In 2025, the conversation has matured, recognizing that the original ending, while painful, reinforced a core theme of the show: life is about the journey and the stories we tell, not just the destination. Ted Mosby, the hopeless romantic, finally got his true love, but he also got the second chance with his first love, completing a full, circular, and very human arc.