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Sex and the City was all about four friends finding love in New York City. For six seasons, Carrie Bradshaw, Miranda Hobbes, Samantha Jones, and Charlotte York dated some interesting men. They all settled down with good guys when the original series ended, but it took time to get there. Some of their dates were great, and others were absolutely terrible. We’ve collected the most cringeworthy date for each Sex and the City character. 

Kim Cattrall, Sarah Jessica Parker, Cynthia Nixon, and Kristin Davis pose for a portrait in an undated photo on the set of the HBO series "Sex and the City."
The cast of ‘Sex and the City’ | Photo Courtesy of HBO/Getty Images

Carrie had a lot of bad boyfriends, and even more bad dates 

Carrie was the one Sex and the City character who found herself in longer-term relationships. While most of Charlotte York’s relationships last an episode, and Samantha Jones didn’t believe in relationships, Carrie dated several men for a bit. Not all of her boyfriends were winners, though. She dated plenty of terrible men, some for a while and some for just a night. 

Sarah Jessica Parker, as Carrie Bradshaw, looks on with an intense stare during an episode of 'Sex and the City'
Carrie Bradshaw | Getty Images

So who was the worst? Carrie’s worst boyfriend was Jack Berger, no question. Her worst date had to be Wade Adams, though. Carrie met Wade when she learned her favorite cobbler had changed locations. Wade owned the comic book store that replaced it. While Wade was cute and fun, he was desperately immature and never wanted to grow up. Wade became Carrie Bradshaw’s most cringeworthy date when he lied to his mom and made Carrie take the fall for the marijuana they were smoking together. 

Charlotte York found a cringeworthy date in Paul Ericson

Charlotte York was never particularly good at picking out good men. She was a little too focused on how rich and good-looking a man was and paid little attention to who they were or whether they were actually compatible. Eventually, she found Harry Goldenblatt, but she went on many cringe-worthy dates to get to him. 

Kristin Davis as Charlotte York poses in a promotional photo for 'Sex and the City'
Charlotte York | Stuart Ramson/Getty Images

Charlotte’s most embarrassing date came in season 2 of Sex and the City when she started seeing Paul Erikson, a recording executive. Paul seemed good on paper, but he had a little problem with adjusting himself in public. Charlotte attempted to remedy the situation by buying Paul a more supportive pair of underwear, which he promptly flipped out over. Paul was especially cringeworthy because of his bad manners, lack of awareness, and clear commitment phobia. 

Miranda Hobbes once dated a man who couldn’t get past his catholic guilt 

Religion has a way of persisting in a person’s psyche, even if they no longer practice. Miranda Hobbes found that out quickly when she briefly dated a playwright, Thomas John Andersen. He seemed like a really good guy until he immediately jumped up after sex to shower. Eventually, Miranda learned that Thomas John Andersen was raised catholic and felt dirty and guilty every time he had premarital sex. 

Cynthia Nixon wearing a green shirt poses for a promotional photo for 'Sex and the City'
Miranda Hobbes | Archivio Apg/Mondadori Portfolio via Getty Images

Thomas John Andersen’s feelings about premarital sex didn’t make him particularly cringe-worthy, but the way he opted to handle it did. He was hypocritical and opted to yell at Miranda when she tried to help him feel that their sexual escapades weren’t particularly shameful. Miranda dated several other cringe-worthy men, but he is probably the worst. 

Samantha Jones slept with a lot of men, but only a few were truly troubling 

Samantha Jones was not like her pals. She didn’t have hangups about her sexual exploits, and she didn’t let men get all that emotionally close to her either. The result was plenty of fun stories but very few truly bad dates. That doesn’t mean they never happened, though. In season 3 of Sex and the City, Samantha Jones dated Len Schneider, a man she wouldn’t have given any attention to if she wasn’t in the midst of an emotional breakdown. 

Kim Cattrall as Samantha Jones sits in a restuarant during a scene for 'Sex and the City.' Samantha Jones went on the most dates on 'Sex and the City'
Samantha Jones | Paramount Pictures/Newsmakers

Samantha met Len when she moved into a new apartment. She was initially put off by the fact that Len, older and very dated, tried to pick her up. When she feared she was entering menopause, Samantha agreed to date Len, only to get her period during sex. The entire storyline was awful and cringe-worthy, and so was Len. To be honest, Samantha should have paid to replace his $2,000 sheets.