She's a stalker and an arsonist. 'Nuff said. But according to Ted, these were mere sweet eccentricities instead of giant, China-sized red flags. The only good thing to come out of his relationship with Jeanette was the death of Ted's red cowboy boots.
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Molly (Misti Traya)
No wonder Ted has women issues! In his junior year of high school, Ted gave Molly his big V-card and declared his love for the girl. While she said it back, Molly was just interested in sex and dumped him afterwards. Way harsh, Tai!
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Karen (Laura Prepon)
When Marshall and Lily hate someone, take note. The pair was never high on Ted's on-again, off-again high school and college girlfriend — and for good reason. Not only did she repeatedly cheat on Ted, but she once "lingered" her stare on a nude Marshall when Lily was painting him (show some respect, woman!). But Karen's biggest flaw: somehow being even more pretentious than Ted.
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Becky (Laura Bell Bundy)
Out of all of Ted's exes, his relationship with Becky might be the most disturbing. The baby talk, tying her shoelaces, her complete, childish dependence on him — it all reeked of creep. And really, boats, boats, boats? Just walk away and never look back.
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Royce (Judy Greer)
Ted isn't exactly a catch. He spends most of his time pining after his ex-girlfriend, constantly tries to show off his intellect, and acts as though he's the only one who's ever wanted for companionship. Yet, Royce is somehow so much worse. Not only does she have a gambling addiction and share a bed with her brother, but she loves The Wedding Bride, which honestly can't be great enough to talk about for days on end. (There's a reason she's been left at the altar three times.)
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Vicky (Courtney Ford)
Vicky is rude to waiters, laughs at old people when they fall and thinks Pablo Neruda is a "turd." Oh, and she fell for the Naked Man! At least Ted's one-night stand with her got him back out there after being jilted, but good lord, she was terrible.
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Jen (Lindsay Sloane)
She dresses up her cats in costumes. Let us repeat: She dresses up her cats in costumes! Dressing up dogs is one thing, but cats? That's going too far.
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Honey (Katy Perry)
Ted once tried to open a bar for pretentious people to discuss poetry. His relationship with the painfully dumb Honey was never going to last. Honey was so naïve, she let her landlord put a camera in the shower for "security" and gave her Social Security number to a stranger claiming to be a Nigerian prince. But her most gullible offense: Believing she was Barney's "first."
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Strawberry (Gina Comparetto)
All we know about Strawberry is was she was a vegetarian with a passion for animal activism. Sometimes she might have taken this hobby a little too far, but unlike many of Ted's "random skanks," at least Strawberry had principles!
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Cathy (Lindsay Price)
Cathy's nice, she's smart, she's attractive — at first glance she seems like a quite the catch. And then she opens her mouth. The sheer amount of words that Cathy says per minute deafens even the most smitten suitor to her other charms.
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Holli (Rebecca Budig)
Holli is proof that sometimes Barney was actually right. Maybe not about the "dirty girls names end in "ly" rule, but apparently the Three Date Rule is legit (at least in the world of HIMYM). After Ted texts Holli, she ends up acting exactly like him and (jokingly?) proposing, planning a trip to Brazil together and more. One Ted is bad enough. Two? That's just torture.
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Blah Blah (Abigail Spencer)
Pro: She plays World of Warcraft. Con: She's totally crazy and ends up committed to Bellevue. Pro: She's super attractive. Con: She's not even crazy enough to make a big enough impression for Ted to remember her name. Can't win 'em all, right?
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Lizbeth (Katy Stoll)
Lizbeth might be emo and super negative, but she's the only one of Ted's dates to ever call him out on being such a weirdo. Plus, she likes lasagna!
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Amanda (Brooke Nevin)
It's one thing to be a bad date, but Amanda is a bad date and bad at her job. Ted met Amanda while eating at her restaurant because he found her hair in his soup. But this wasn't just a fluke. When she makes a cake for Lily's 32nd birthday, the dessert reads, "Happy 42nd Birthday Lori." Not gonna recover from that one, "Bertha."
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Zoey (Jennifer Morrison)
One-third of their relationship was spent fighting over a building, another third was spent repressing feelings while she was married to The Captain, and the other third was when they were actually dating. That just equals a complete disaster! It's great that Zoey cares about stuff and all, but sheesh! Can't she ever just relax?
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Stacey (Janet Varney)
Ted loves bass players and everyone loves yoga chicks. But you know who we don't love? People who say, "See ya later, alligator" every time they say goodbye. Nerd alert!
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Marybeth (Kathleen Rose Perkins)
Part of us feels bad for Marybeth. She spent her entire New Year's Eve driving around in a limo with a date who was in love with someone else (who was also in the limo). Talk about awkward! However, it's still unknown whether Marybeth was even really into Ted or just way too friendly with everyone.
18 of 33 Monty Brinton/CBS/Landov
Amy (Mandy Moore)
Sure, you can count on Amy to steal booze for you, but she's not exactly trustworthy — unless you're totally OK with her ex giving you a butterfly tramp stamp while you're drunk.
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Victoria (Ashley Williams)
Victoria is considered "the one who got away" after Ted lied and was about to cheat on her with Robin. And frankly, we wish the show had just left it at that. Her return in the later seasons was time-wasting at its best and grating at its worst. Who leaves their fiancé at the altar and makes the guy they're running away with deliver the Dear John letter? Victoria. Who gives a Friends-esque ultimatum (it's me or her) as an answer to a marriage proposal? Victoria. Plus, those snowflake shoes are way too cutesy for our taste.
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Holly (Karissa Vacker)
Ted and Holly might have had a chance if Ted wasn't being Ted. The mere mention of her ex's name, Wayne, and his lack of manners, causes him to think of Wayne Manor, then Batman and then Robin. (Not Dick Grayson, obviously.)
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Trudy (Danica McKellar)
Trudy is up for threesomes, but she is responsible for The Pineapple Incident and we never learned where the spiky fruit came from.
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Rachel (Busy Philipps)
Like Trudy, she's up for threesomes (with Trudy), but as Lily notes, "all sorority girls are sluts." Not that she's an impartial judge of character since Rachel was the boot-snatcher she had met in a shoe store earlier that day.
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Natalia (Bar Paly)
A gourmet cook who can recite Caddyshack word for word sounds like quite a catch, right? Too bad both Ted and Barney ditch her mid-date for other women. But it's just as well since Natalia's work visa was set to expire.
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Robyn (Cristen Irene)
Or should we say "Yobin" since she's "Robyn with a 'Y'"? A Canadian scotch and gun enthusiast, Robyn is basically the blonde, boring version of Robin who only made Ted think about "Robin with an "I.'"
25 of 33 Monty Brinton/CBS/Landov
Stella (Sarah Chalke)
Sure Stella made Ted move to New Jersey and, oh yeah, dumped him on their wedding day for her ex. But she was the first true grown-up relationship he had and outside of Robin, and she remains a friendly ex. Plus, we'll always be jealous of that two-minute date.
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Carly (Ashley Benson)
Carly, aka Barney's college-age half-sister, could've have been the future Mrs. Mosby, as many fans speculated before her appearance, if Ted were 10 or so years younger. After all, they share a love of Star Wars, even though she's only seen the "new" ones.
27 of 33 Monty Brinton/CBS
Naomi (Katie Holmes)
In many ways, the Slutty Pumpkin and Ted were perfect for each other. They waited 10 years to meet, and neither could bring themselves to end it despite being fully aware that they were not clicking. Naomi gets props for finally having the balls to do so and in turn letting Ted off the hook. But ladies, please don't wear the same Halloween costume for years just to find a guy.
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Natalie (Anne Dudek)
Oh, Natalie. We'd give you grief for getting back together with Ted twice after he dumped you on your answering machine on your birthday. But we'll always love you, you Krav Maga goddess, for doing what many of us have wanted to do to Ted over the years: beat the crap out of him.
29 of 33 Cliff Lipson/CBS
Cindy (Rachel Bilson)
It's petty for Cindy to resent The Mother for stealing all her boyfriends and Ted for having things in common with The Mother, but it's kind of awesome that she became a lesbian after dating Ted. Besides, if it weren't for her recommending The Mother's band for Barney and Robin's wedding, Ted might still be looking for the missus now.
30 of 33 Robert Voets/CBS/Landov
Mary (Erinn Bartlett)
Mary the paralegal is the definition of brains and beauty, and she rightfully slapped Ted when he thought she was a prostitute. But Barney's to blame for that one.
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Janet (Amber Stevens)
Janet is a genius, organ-donor billionaire heiress who has conquered Mount Everest and, most importantly, loves Annie Hall — none of which Ted would've known about on their first date if he hadn't broken their promise not to look each other up online. Let's face it though: Janet was too good for Ted anyway.
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Robin (Cobie Smulders)
Robin and Ted are like fetch: not going to happen. While their yearlong relationship had some great moments, like the discovery of Robin Sparkles, their different dreams in life always meant that they wouldn't work out. Not that that has stopped them from being friends with benefits or Ted from still pining after her. And though Robin isn't "The One" for Ted, she is a great friend.
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The Mother (Cristin Milioti)
OK, we don't know that much about her yet and Future Ted's narration might be biased, but it's clear that he will meet his match that rainy night on the train platform. After all, she appreciates a good "shellfish-selfish" joke, makes breakfast foods sing show tunes and apparently owns the only yellow umbrella in New York City.