Played by: Misti Traya Ted lost his virginity to Molly at age 17.
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Played by: Laura Prepon Ted's high school girlfriend, then his on-again, off-again girlfriend through college, Karen repeatedly cheated on him.
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Played by: Anne Dudek ''Krav Maga girl.'' They dated in 2002 and again in 2005. Ted broke up with her on her birthday?twice.
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Played by: Lindsay Sloane Ted went on two blind dates with Jen — one in September 2002, the other in September 2009.
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Played by: Cobie Smulders Had their first date in the pilot where Ted stole a Blue French Horn for her. The rest is history.
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Played by: Danica McKellar In what is now known as ''The Pineapple Incident,'' Trudy left the tropical fruit in Ted's room after they hooked up.
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Played by: Ashley Williams Pastry Chef Ted met at Stuart and Claudia's wedding. They dated on and off. They first broke up because Victoria moved to Germany and ultimately because Ted refused to cut Robin out of his life.
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Played by: Busy Philipps Ted attempted to have a three-way with Trudy and her sorority sister, Rachel.
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Played by: Abigail Spencer Ted dated this nameless lady in the fall of 2007 after they met online playing World of Warcraft.
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Played by: Lindsay Price Talks. A lot.
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Played by: Gina Comparetto A militant hippie vegan Ted dated when Marshall graduated from law school.
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Played by: Sarah Chalke Ted met the dermatologist while having a tattoo removed. They eventually got engaged, but Stella left Ted at the altar.
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Played by: Rachel Bilson An economics PhD student at the college where Ted works. More importantly, she was Mother's roommate.
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Played by: Brooke Nevin According to Lily, one of Ted's ''random skanks.'' Ted brought her to Lily's 32nd birthday party as his date, and she ended up in the group photo.
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Played by: Judy Greer Ted saw The Wedding Bride with her.
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Played by: Laura Bell Bundy Robin's co-anchor known for her ''Boats, boats, boats!'' commercial.
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Played by: Jennifer Morrison Formerly married to The Captain, Ted and Zoey met when she was protesting the new GNB building that Ted was designing.
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Naomi ''The Slutty Pumpkin''
Played by: Katie Holmes Marine biologist Ted met at a Halloween party who was initially one of the ''Ones that got away.'' They reconnected a few years later only to realize they don't connect.
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Played by: Ashley Benson Barney Stinson's sister, went on a few dates with Ted in episode 814, ''Ring Up!''
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Played by: Abby Elliot The last woman Ted dates before settling down. Crazy stalker. Police woman.