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Of all the four main characters on Sex and the City, the most cynical about love and dating is Miranda Hobbes (Cynthia Nixon). After years of romantic hits and misses, Miranda finally marries her on again off again love interest, Steve Brady.

RELATED: Sex & The City: 10 Times Miranda Hobbes Was The Best

Like all the ladies, Miranda endures the ups and downs of being a successful single woman dating in New York City. This means going on dates, hoping one will lead to true love or at least good sex. Most of the time, it just means Miranda meets and sleeps with some serious freaks.

10 The Modelizer: Models And Mortals (Season 1)

First dates can be agonizing, but when Miranda attends a dinner party with sports agent Nick Waxler, she finds herself having a great time. Her optimism is short-lived when she’s blindsided with the news that Nick is a “modelizer.” He only dates models, well, because he can.

The only reason he asks Miranda out is that his friends issue him an ultimatum: bring a woman around with something to offer besides looks. Nick gets his pals off his back, but Miranda learns she’s just his “intellectual beard” for one night.

9 The Guy Who Likes Spanking: Secret Sex (Season 1)

Miranda meets sports medicine doctor Ted Baker during a kickboxing class. After she accidentally kicks him in the face, the two begin dating. Finding herself alone in Ted’s apartment, Miranda does what most women do when embarking on a new relationship: she ransacks his apartment. She isn’t surprised to find porn, but she is shocked to learn her new man appears to have a spanking fetish.

Unable to confront him with what she’s found, Miranda deliberates if this kind of kinkiness is a dealbreaker or not. But after sharing a great meal, Miranda drops a playful hint about Ted’s proclivity for discipline. And just like that, Ted stops calling or returning texts and Miranda never sees him again. Ted isn’t comfortable with Miranda bringing up his secret shame.

8 The Guy Who Loves Sex In Public: La Douler Exquise! (Season 2)

Miranda and Jack share a love for historical biographies, but Jack has another passion — sex in public places. Miranda realizes Jack only seems interested in sex if there’s the risk of someone catching them in the act.

RELATED: Sex & The City: 10 Times Samantha Jones Won At Life

When he finally brings her back to his apartment, Miranda finds out they aren’t alone: Jack’s parents are visiting, and he is determined to finish, even as they prepare to walk into the room. Jack’s idea of meeting the parents proves to be too much for Miranda.

7 The A**hole: Frenemies (Season 3)

Miranda hits a new low when she’s stood up by an urban planner only to learn he died. She attends his funeral and encounters a seemingly great guy, Jim. Jim also once dated Carrie, who warns Miranda that Jim is an a**hole. Miranda proceeds to discount Carrie’s advice and goes out with the civil engineer.

But when Miranda insists Carrie join them for drinks to give the new and improved Jim a chance, he shows his true colors. Still salty over his breakup with Carrie eight years earlier, Jim turns into a jerk, insulting Carrie at every turn. This leads to an unpleasant threeway confrontation, and Miranda learns that once an a**hole, always an a**hole.

6 Manhattan Guy: The Freak Show (Season 3)

Carrie begins to wonder if there are any normal men left to date in NYC until she meets a cute magazine editor named Ben. Convinced she’s possibly found a potential keeper, Carrie decides to set Miranda up with one of his friends, and the foursome goes on a double date.

Things start okay, but over ice cream cones, Miranda learns this not so Prince Charming is not only convinced that NYC is the center of the universe, he’s never left Manhattan in 10 years. He ridicules anyone who feels a need to leave for any reason … ever. Suddenly, Miranda has to feed her cat, and it’s bye-bye, Luke. The force isn’t strong with this one.

5 Hair Plug Guy: Evolution (Season 2)

Miranda goes on a first date with Joseph Adler. The revelation that she has a “lazy ovary” makes Miranda feel a bit vulnerable and desperate enough to go to dinner with a man with hair plugs. There’s no shame in Joseph’s game, who is proud of his newly sprouting follicles.

RELATED: Sex And The City: 10 Times The Characters Should Have Probably Gone To Jail

When Miranda opens up to him about her reproductive conundrum and the possibility of freezing her eggs, Joseph has strong opinions on the subject, and none of them are good. He considers reproductive science a last-ditch effort for desperate women. Miranda suggests a man doing “crop rotation” on his head doesn’t need to lecture her about science. Maybe it’s the hormones, or maybe it’s just Joseph’s insensitivity, but this couple was DOA before dessert.

4 The Sexy Cop: What Goes Around Comes Around (Season 3)

Carrie’s misfortune turns out to be good luck for Miranda. After Carrie is mugged, sparks fly between Miranda and Detective Stevens. Miranda considers the hunky police officer to be out of her league. During their second date, she can’t help but notice other women noticing him, and to compensate for her anxiety and low self-esteem, she downs cocktail after cocktail.

A sloppy, drunk Miranda can overcome her nerves, but she wakes up the next morning to no flower, no Detective Stevens, and no love note – just the number for her local Alcoholics Anonymous chapter.

3 The Angry Guy: The F**k Buddy (Season 2)

Fighting in court is one thing, but when Miranda dates another attorney with a horrible attitude, she learns he’s constantly on the defensive. He complains about everything, from the price of movie tickets to the best way to hail a cab. Miranda puts up with his attitude, blaming it on work stress and hopeful he’ll lighten up if he makes partner.

In the meantime, she’s okay with trading some verbal abuse for good sex. But while on a date to celebrate Kevin’s big promotion, he’s just as miserable as ever, with no finish line in sight. For once, Miranda is the optimistic one and dumps Kevin on the spot, telling him to “never, never” call her again.

2 The Guy With The Kid: Shortcomings (Season 2)

When Miranda meets Roger, she’s dubious about dating a divorced man with a kid, especially when the kid is a brat with bladder control problems. Roger turns out to be the “heterosexual Holy Grail,” which means she’s willing to put aside her concerns about his baggage.

After spending the night together, a naked Miranda has an unexpected run-in with Roger’s son, which leaves the boy in need of stitches. Accident or not, neither father or son is sad to see Miranda go since bloodshed is never indicative of a good date.

1 The Married Guy: The Man, The Myth, The Viagra (Season 2)

While watching a lousy comedian at a comedy club with divorced architect Alan, Miranda learns Alan is still married. She finds out when his wife calls his cell phone and Miranda answers.

This is bad enough, but the entire drama unravels and becomes public information, thanks to the comic who seizes the opportunity to humiliate Miranda, who storms out a laughingstock.

NEXT: Sex And The City: 10 Reasons Samantha And Charlotte Aren’t Real Friends


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