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8. Naomi, aka the Slutty Pumpkin

Played by: Katie Holmes. First appearance: "The Slutty Pumpkin Returns" (Season 7, episode 8). After a long-ago encounter at a Halloween party, Ted finally finds Naomi a decade later. It turns out she had been looking for him too, and they start dating. The reality doesn't live up to the fantasy, however, and they go their separate ways amicably.CBS