‘Sex and the City’: Charlotte York’s Best and Worst Boyfriend

When Sex and the City fans first met Charlotte York, she was introduced as a “gallerina.” Her art history degree helped her land a job in one of Manhattan’s art galleries, and while she was a consummate professional at work, her real goal was to leave the art world behind to become a wife and stay-at-home mother. While she ultimately got what she wanted, the road to get there wasn’t as easy as Charlotte initially thought. She kissed a lot of frogs to find her prince. So, who was Charlotte’s absolute worst and absolute best boyfriend during the show’s run?

How many people did Charlotte York date during all six seasons of Sex and the City?

Smith-educated Charlotte came from a rich world. Her father, a doctor, and her mother, a socialite, raised Charlotte and her brother, Wesley York, in a rich enclave in Connecticut. She went to college and expected to get married young to a man from a similar background. Her life objective led her to date a fair number of men. Most turned out to be awful.

Kristin Davis sits at the 23rd and Broadway Dogwalk holding a Cavalier King Charles Spaniel during a scene for 'Sex and the City' in 2003
Kristin Davis | James Devaney/WireImage

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During the show’s six-season run, Charlotte dated 18 different men. Somewhat surprisingly, the majority of those relationships were incredibly short-lived. Most people would have considered most of her romances casual dates rather than relationships. Charlotte only ended up having two serious, long-term relationships in the six years that Sex and the City fans had to get to know her. Both of those relationships resulted in marriage.

Charlotte York’s worst boyfriend didn’t last long

While some Sex and the City fans would argue that Trey MacDougal was Charlotte’s worst relationship because of his meddling mother, he wasn’t all bad. Sure, Trey had flaws, but in the end, he wanted to see Charlotte happy, even though it would not be with him. Plus, Charlotte’s dating life before Trey wasn’t exactly impeccable. The worst boyfriend award must go to Ned, the mourning widow.

Kristin Davis as Charlotte York and Sarah Jessica Parker as Carrie Bradshsaw sitting on a bench in Central Park during a scene for 'Sex and the City' in 2001
Kristin Davis as Charlotte York and Sarah Jessica Parker as Carrie Bradshaw in ‘Sex and the City’ | Tom Kingston/WireImage

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Charlotte met Ned at a cemetery in “Four Women and a Funeral,” the fifth episode of season 2. Charlotte was attending the funeral of a fashion designer, and Ned was at a different gravesite mourning the loss of his wife. Ned told Charlotte all about his late wife and had her believing he was a caring and sensitive man. Later, she found out that Ned was exploiting his wife’s death to get women to sleep with him. Many troubled guys walked into Charlotte, Carrie Bradshaw, Samantha Jones, and Miranda Hobbes’ lives, but Ned has got to be the worst.

Charlotte found true love with Harry Goldenblatt

Charlotte didn’t find forever after her first trip down the aisle. She did the second time she said, “I Do”, though. Charlotte met Harry Goldenblatt during her divorce proceedings. He served as her divorce lawyer. While he was instantly smitten with Charlotte, she didn’t think he was a suitable partner. Eventually, Harry’s sweet nature won her over, and they fell into an easy relationship. Charlotte realized she wanted to marry Harry when he told her he had no problem with adopting children if they could not have kids of their own.

Kristin Davis and Evan Handler are photographed standing on Le Carrousel in Bryant Park with their on-screen daughter during the filming of 'Sex and the City: The Movie'
Kristin Davis as Charlotte York-Goldenblatt, Alexandra Fong as Lily Goldenblatt and Evan Handler as Harry Goldenblatt | Arnaldo Magnani/Getty Images

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The couple married in the final season of Sex and the City and adopted their daughter Lily. In Sex and the City: The Movie, their family was completed by a surprise pregnancy. While Evan Handler, the actor who portrayed Harry, hasn’t yet confirmed his involvement in And Just Like That, the Sex and the City reboot, fans are certain that Harry and Charlotte are still deeply in love.