Charlotte York's love life may not have always been the picture-perfect fairytale she hoped for, but that never stopped her from believing in true love. Out of Samantha, Miranda, and Carrie, Charlotte was the most romantic, always holding out hope for her knight-in-shining-armor to rescue her from the cynicism of urban New York living.
Her values helped shape her standards, and she didn't believe in wasting time going on endless dates if they didn't lead to something meaningful. This caused her to rush into marriage a little too prematurely, but it also helped her realize her own value as a human being. And while Charlotte could be very traditional, she took off her velvet hairband every now and again to expose her wild side.
WOULD LOVE TO DATE: BAIRD JOHNSON
In Season 3, Charlotte's gallery scores one of the biggest talents in the city, whose work manages to shock even the most apathetic of New Yorkers. Baird Johnson's head-turning photographs involve women dressing as men, from Wall Street financiers to greased-up construction workers, and the hyper-feminine Charlotte is intrigued by both the prints and their creator.
When he asks to photograph her in a similar style to his models she balks, but soon the persuasive Baird is helping her inner man emerge. They didn't date for long, but he encouraged her to step outside her comfort zone and embrace another side of herself.
WOULDN'T: PAUL ERICSON
Charlotte plays the field a lot in Season 2, but strikes out in "Take Me Out To The Ballgame", where she introduces the girls to her date de jour, a sleazy music producer with a tendency to firmly grab his crotch like at any moment it might wander off.
At first, Charlotte believes this to be an issue caused by a lack of breathable underwear, so she gifts him an expensive pair to luxuriate in and stop itching his privates. He's insulted by the gesture and explodes in anger, leaving her to wonder how a grown man could behave like such a toddler.
WOULD LOVE TO DATE: HARRY GOLDENBLATT
Harry Goldenblatt wasn't Charlotte's type at all initially; he was bald, slightly overweight, and was prone to wandering around with mustard stains on his shirt. But despite not looking like her typical Prince Charming, he turned into it over time, winning her over with his warmth, humor, and ion.
Charlotte met Harry in Season 5, when he was handling her divorce from Trey, and had it not been for Harry's steadfast dependability, even a perpetual romantic like Charlotte might have lost faith in true love.
WOULDN'T: ARTHUR
When Charlotte first met Arthur, she thought he was a perfect match for her in every way; he was successful, handsome, and fought off another man to win her hand. She found his brutish chivalry charming before knowing to what extent it overshadowed his life.
Eventually Charlotte found that Arthur had a way of taking offense at everything, from standing in line for a movie to sitting down to a nice dinner at a restaurant. Eventually Charlotte could no longer pretend not to notice his outbursts, and left him before he took out his anger problems on her.
WOULD LOVE TO DATE: TREY
Trey MacDougal embodied everything Charlotte hoped to find in a husband, which prompted her to break her own rules and do the proposing after knowing him for just a few short weeks. Trey was handsome, had a successful career as a doctor, and came from an established family - what wasn't to love?
Unfortunately, Trey had some intimacy problems that, coupled with Charlotte's stubborn drive to have a perfect nuclear family, caused their marriage to implode. If Trey had been able to freely communicate his feelings, they might have been able to work things out. As it was, he proved to be a gentleman during their divorce proceedings.
WOULDN'T: NED
When Charlotte encountered a sensitive and sorrowful man mourning the loss of his wife in Season 2, she felt her heartstrings pulled her towards him. It never occurred to her that he could be performing an elaborate ruse to garner sympathy and sex from empathetic women.
Charlotte turned out to be one of many women who Ned had cajoled into feeling sorry for him. His truly heartless charade was not only insulting to her, but real widowers everywhere.
WOULD LOVE TO DATE: MIKE
Charlotte's standards often crept into the impossibly high category when it came to her boyfriend's bedroom antics, and Mike was no exception. She was nervous about the fact that he was uncircumcised, to the point where she persuaded him to get cut just so he could sleep with her.
Mike seemed perfectly well adjusted until Charlotte made him feel abnormal and insecure. Suddenly he was forced to change an aspect of his anatomy for her, which had the roles been reversed, would have been written as the shallow and loathsome act that it should have been presented as.
WOULDN'T: JACK
One of the first boyfriends fans see Charlotte date in Season 1, Jack is a charming architect and philanthropist who pushes Charlotte to divulge her deepest fantasies. This is merely a means to discuss his own, which he eagerly s Charlotte participating in.
Jack's fantasies include having a threesome, something Charlotte is initially uncomfortable with. She goes through with it for him, but eventually finds out the hard way that three's a crowd when he selfishly ditches her for the woman they seduce together.
WOULD LOVE TO DATE: STEPHAN
Stephan starts off as one of Charlotte's dear friends in New York City, a pastry chef with a broad knowledge of musical theater and a keen eye for fashion and interior design. This leads her to believe he has to be gay, until he plants a steamy kiss on her.
The girls are unnecessarily rude when discussing Stephan, and ultimately Charlotte dumps him because she views him as too effeminate for her. They both scream at the sight of a mouse and that's that, despite the fact that he was handsome, a spectacular cook, and actually expressed his emotions freely.
WOULDN'T: BRAD
Season 3 finds Charlotte dating Brad, a seemingly normal suitor who ends up being a horrible kisser. Whenever he leans in to an embrace, his lips attack Charlotte's nose and his tongue darts in and out of her nostrils like an eel into a cave.
A surprisingly patient Charlotte tries to coach him in the subtle art of kissing, but his enthusiasm bubbles to the surface, sending him spiraling into overdrive until her face is thoroughly hydrated.