Karen repeatedly cheated on him.

Natalie

Played by:Anne Dudek

“Krav Maga girl.”

They dated in 2002 and again in 2005.

Misti Traya, How I Met Your Mother | Played by: Misti Traya Ted lost his virginity to Molly at age 17.

CBS

Ted broke up with her on her birthday, twice.

The rest is history.

Cathy

Played by:Lindsay Price

Talks.

Josh Radnor, Laura Prepon, … | Played by: Laura Prepon Ted’s high school girlfriend, then his on-again, off-again girlfriend through college, Karen repeatedly cheated on him.

Sonja Flemming/CBS

Stella Zinman

Played by:Sarah Chalke

Ted met this dermatologist while having a tattoo removed.

They eventually got engaged, but Stella left Ted at the altar.

More importantly, she was Mother’s roommate.

Anne Dudek, How I Met Your Mother | 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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Royce

Played by:Judy Greer

Ted sawThe Wedding Bridewith her.

They reconnected a few years later only to realize they didn’t connect.

Jeanette Peterson

Played by:Abby Elliott

The last woman Ted dates before settling down.

Lindsay Sloane, How I Met Your Mother | 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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Josh Radnor, Cobie Smulders, … | 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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Josh Radnor, Danica McKellar, … | 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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Josh Radnor, Ashley Williams, … | 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

Cliff Lipson/CBS

Josh Radnor, Busy Philipps, … | Played by: Busy Philipps Ted attempted to have a three-way with Trudy and her sorority sister, Rachel.

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Josh Radnor, How I Met Your Mother | 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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Josh Radnor, Lindsay Price, … | Played by: Lindsay Price Talks. A lot.

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Josh Radnor, How I Met Your Mother | Played by: Gina Comparetto A militant hippie vegan Ted dated when Marshall graduated from law school.

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Josh Radnor, Sarah Chalke, … | 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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Josh Radnor, Rachel Bilson, … | Played by: Rachel Bilson An economics PhD student at the college where Ted works. More importantly, she was Mother’s roommate.

CBS

How I Met Your Mother | 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

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Judy Greer, Josh Radnor, … | Played by: Judy Greer Ted saw The Wedding Bride with her.

CBS

Laura Bell Bundy, How I Met Your Mother | Played by: Laura Bell Bundy Robin’s co-anchor known for her ‘‘Boats, boats, boats!’’ commercial.

Matt Kennedy/CBS

Josh Radnor, Jennifer Morrison, … | 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.

Monty Brinton/CBS

Josh Radnor, Katie Holmes, … | 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

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Josh Radnor, How I Met Your Mother | Played by: Ashley Benson Barney Stinson’s sister, went on a few dates with Ted in episode 814, ‘‘Ring Up!''

CBS

How I Met Your Mother | Played by: Abby Elliot The last woman Ted dates before settling down. Crazy stalker. Police woman.

Ron P. Jaffe/CBS