On Sex and the City, Charlotte York (Kristin Davis) is the most traditional one out of the foursome. From the start, she only dates a man if she sees the potential for a long-term commitment.
Charlotte is such a fan of the institution of marriage that she does it twice. Before settling down with her sweet schlub of a hubby, Harry, Charlotte has a very specific type. She dates wealthy men who look great on the outside, but whose personalities and proclivities aren't up to Charlotte's high standards. This means when it comes to courtship, Charlotte's track record includes more duds than studs.
The Guy Who Gets Circumcised: Old Dogs, New Dicks (Season 2)
When dating restaurant critic Mike, Charlotte comes across something she's never seen before -- an uncircumcised penis. This throws the Episcopalian princess for a loop. Charlotte subscribes to the school of it's what on the outside that counts, so she decides to cut Mike loose until he tells her he's going to groom his "Shar-Pei" so to speak.
Once Mike is healed and good to go, he and Charlotte spend their first night together. Charlotte is ready to move forward as a couple, but Mike has other ideas. He's eager to dip his new wick whenever and wherever he can. It's a little tough to feel bad for Charlotte when this deluded fairytale comes to a close since she kind of deserves it after being so shallow.
The Movie Star: The Caste System (Season 2)
It's rare for Charlotte to date without an agenda: every new suitor has the potential to be a groom. But when movie star Wiley Ford strolls into her gallery and takes an interest in more than the art, Charlotte throws all her rules out the window. She becomes Wiley's groupie for the day and an object of ridicule for his entourage. Riley's used to being adored and assumes this gives him a free to be a disgusting pig, but when he requests that Charlotte do something too pornographic to include here, she decides her date with Wiley is officially over.
The Bad Kisser: No Ifs, Ands, Or Butts (Season 3)
After an amazing first date, Charlotte is disheartened to discover Brad is a bad kisser. This is a potential dealbreaker, but Charlotte isn't ready to give up the possibility of happily ever after without exhausting all of her options.
So on their next date, Charlotte takes control of the situation and conducts a Kissing 101 class. At first, Brad seems to get it, but then quickly goes back to his old ways, forcing Charlotte to break up with this clueless Lothario. It also leaves her emotionally and physically bruised.
The Guy Who Gives Her Crabs: Twenty-Something Girls vs. Thirty-Something Women (Season 2)
Charlotte meets 26-year-old Greg on the Hampton Jitney. Their date is one long weekend of Jell-O shots, bonfires, beer bongs, and other twenty-something hijinks. Charlotte enjoys revisiting her '20s until she discovers her weekend with Greg leaves her with a case of crabs. In the city, Charlotte is pretty conservative and cautious, and unsurprisingly, she takes the outdated view that an STD is 'dirty' or says something terrible about the person.
The One Who Wants Head: The Monogamists (Season 1)
Charlotte believes every guy she dates is the ONE, and Michael is no different. They have a meet-cute moment in the park, and Michael seems perfect. Even his dog is perfect. But if Charlotte wants to get down the aisle, Michael expects some concessions, including Charlotte performing a certain act.
Charlotte isn't a fan of fellatio (she has a sensitive gag reflex), and when she breaks the news to Michael, he's more concerned about the prospect of a future without oral than Charlotte's comfort level. Once Charlotte realizes this prince is a frog, she's not open to his idea of compromise -- licking another area instead.
The Groomsman: The Chicken Dance (Season 2)
Bridesmaid Charlotte immediately hits it off with groomsman, Martin. The two manage to cram three dates into one evening. There's dinner, dancing, and sex. They fantasize about what their life will be like together over the first course. Martin goes so far as to introduce Charlotte to his parents, and that's when things fall apart. Martin's father, whose supposed commitment to his marriage and family is something Martin aspires to emulate, grab's Charlotte's ass.
What Martin doesn't know about dear old dad is that he tends to be handsy when dancing with a beautiful woman like Charlotte. When she tells Martin about his father's inappropriate behavior, Martin proves the adage that blood is thicker than water, insisting some woman wearing a slutty dress would never cause his dad to stray. Yet, another potential Mr. Right turns out to be Mr. Wrong.
The One Who Wants A Threesome: Three's A Crowd (Season 1)
Charlotte considers expanding her horizons sexually when her new boyfriend, Jack, suggests they have a threesome. While certain acts are non-starters for Charlotte, she finds herself more amenable to fulfilling Jack's request. At a fundraising benefit, they find the perfect pinch hitter, but once things start to heat up, Charlotte finds herself the odd woman out. It turns out Jack's fantasy doesn't include Charlotte after all.
Mr. P***y: Freak Show (Season 2)
During a girls' night out, Charlotte catches the eye of Mitch Saylor, aka "Mr. P***y." Mitch is so good at going down, he's earned quite the reputation among the single women in NYC. Charlotte confuses having multiple orgasms with having a relationship, and she decides to take Mitch for a spin outside the bedroom.
Mitch makes Charlotte happy under the sheets, but during an awkward dinner date, she realizes for someone so good at oral sex, Mitch doesn't have much to say or anything else to offer. He also does unspeakable things to a fig which is the death knell for Charlotte and Mr. P.
The Guy Who Shares A Cab: Pilot (Season 1)
Charlotte makes a mistake by playing hard to get. The notoriously "un-gettable" Capote Duncan is a catch, so Charlotte has to be at the top of her game. She heads back to his apartment to see a painting but cuts the night short. Capote hops in Charlotte's cab on the hunt for another female companion for the night. This "toxic bachelor" can't even wait and find his own ride. He gets points for being honest so Charlotte doesn't waste her time and can use it more productively revisiting her copy of The Rules.
The Cheater: The Cheating Curve (Season 2)
Charlotte decides to mix business with pleasure and bring her latest love interest, Gareth, as her plus one to her gallery's art opening. While Charlotte is busy selling to paintings to power lesbians, Gareth is in the back rounding first base with another woman. Charlotte and Gareth aren't serious, but it's still in very bad taste to make out with a random woman while on a date with another. Gareth is unapologetic when he gets caught because he doesn't consider kissing cheating. Maybe not, but sticking his tongue down someone else's mouth while on a date with Charlotte is in very bad taste.