Natalie (Anne Dudek)
Ted broke up with Natalie on her birthday. Twice! First over her answering machine with her friends listening as they gathered for her party. Then after winning her back, he realizes it's not going to work and he broke up with her again, this time in person. However it was unfortunate that he failed to remember it was her birthday once again.

Rating: 3.0 / 5.0 (1 Vote)
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HIMYM Quotes

Ted [to Stella in his dream encounter]: You picked the wrong guy.
Stella: Ted?
Ted: You picked the wrong guy. You made a really, really, really bad choice. What were you thinking? That guy? Are you kidding me? Have you learned nothing in the last eight years? You're just gonna regret this. You know that, right? You are going to regret this, and now there is nothing you can do about it because it's too late. All you can do now is go up there and start your crappy, disappointing life that will never be nearly as happy as the one you could have had with me. Good-bye.
Stella: Ted, wait.
Ted: Look, Stella, I am not here to win you back. I am here because I need to know that you know you made the biggest mistake of your life.
Stella: I know

Robin, get me my legal pad. It's Pros and Cons Time!

Ted