As the most complex, dynamic, and free-spirited leads on Sex and the City, Carrie represented a single modern woman just trying to make her way in the urban dating jungle of New York City. Even though she wrote a popular sex column, her sex life was complicated and so were her many boyfriends.
The men in Carrie's life were as multi-faceted as she was. Some were rich handsome millionaires who could have afforded to buy her a closet full of designer shoes several times over, while others were soulful men whose wealth came in their ability to love her unconditionally, and some were just plain bad news. Here are 5 of Carrie's boyfriends we'd love to date and 5 we wouldn't.
WOULD LOVE TO DATE: AIDAN SHAW
With his laconic country charm, down to earth attitude, and gorgeous furniture making skills, Aidan Shaw was one big hunk of man when Carrie met him in Season 3. Carrie would date him at two different times, both jeopardized by her feelings for Mr. Big.
Despite Carrie's flighty nature and inability to commit, Aidan's easy-going personality helped him weather her many moods. He was unwavering in his love for Carrie, but their timing was always off.
WOULDN'T: ALEKSANDR PETROVSKY
A globe-trotting sophisticate and a world-renowned artist, Aleksandr Petrovsky swept Carrie off her feet in Season 6 with his Old World charm and his deep sensitivity. He even invited Carrie to live with him in Paris while he worked on his next museum installation.
As well-meaning as Petrovsky was, his first love would always be his work, leaving no room for Carrie. He could be cold, brooding, and towards the end of their relationship selfish and completely self-absorbed. Carrie needed someone between Prince Charming and Doctor Zhivago.
WOULD LOVE TO DATE: MR. BIG
Mr. Big, aka John James Preston (as Carrie eventually found out), was one of New York City's most eligible bachelors, a business tycoon, and a scoundrel. He toyed with Carrie's heart from the first season to the last season but eventually decided to commit to their connection.
While he could be emotionally unavailable and selfish, Big represented a necessary foil for Carrie. She could never be happy with a relationship that wasn't exciting, even if it was unhealthy. She had as many issues as he did, and ultimately they decided to work on them together.
WOULDN'T: JOHN MCFADDEN
After becoming lonely due to her recent romantic hangup with Mr. Big, Carrie invited her Friend With Benefits John McFadden over to her apartment for a romp in the hay and some cheap Chinese food. He was both low-commitment and boosted her self esteem with no strings attached.
While John filled a particular need that Carrie had, and scratched a certain itch, it was a mistake for her to try to turn him into boyfriend material. They couldn't duplicate the uncomplicated nature of their arrangement by suddenly complicating it with dating.
WOULD LOVE TO DATE: JACK BERGER
He couldn't quite measure up to Aidan or Mr. Big, but Jack Berger occupied a special place in Carrie's heart for a few seasons. A fellow writer like Carrie, he had a certain boyish charm and witty sense of humor when he wasn't playing the role of broody creative.
Even with all his baggage from his past relationships and his issues with insecurity as an author, he was much less of an archetype than any of Carrie's other boyfriends. Unfortunately, he may have been a little too real and brutally candid for Carrie, resulting in her heart being broken.
WOULDN'T: BILL KELLEY
Carrie met city treasurer Bill Kelley in Season 3, and she found it thrilling that he pursued her with intensity and took her to fancy socialite parties. What she didn't find so exciting was his need to control their relationship as he acquired bigger political aspirations.
Bill went from trying to convince Carrie to entertain his fetishes during their lovemaking to ending things with her because suddenly dating someone who wrote a sex column threatened to ruin his image.
WOULD LOVE TO DATE: JOE STARR
Joe had a lot of potential with Carrie when he arrived on the scene at the start of Season 2. He played professional baseball for the New York Yankees, was in great physical condition, and had a killer smile.
Despite the fact that he was an All-American hunk with a prominent place of adoration among New Yorkers, Carrie let her relationship with Mr. Big get in the way and prevent her from seeing Joe's true potential.
WOULDN'T: RAY KING
Carrie thought she hit the jackpot with Ray King, an energetic jazz musician who she met in Season 4. Mr. Big detested him for both his interest in Carrie and his jazz, but Carrie didn't care because his lifestyle was enticing.
While it was a boon for Carrie to be able to flit between chic uptown bars with a well-liked artist, she found that one-on-one, he was far too hyperactive for her taste. He had zero impulse control and Carrie didn't see a place for herself in his frenetic future.
WOULD LOVE TO DATE: DR. BRADLEY MEEGO
Carrie met Dr. Bradley Meego at one of her book's press events and ended up running into him again at the Hamptons when she took a long weekend with Miranda, Charlotte, and Samantha. Not only was he a successful doctor, but he was also cute, polite, and charming.
Carrie didn't really give Dr. Meego a chance because she was too wrapped up in her thoughts about Big. He gave her every chance to pursue something further but ultimately, she returned to New York City without him.
WOULDN'T LOVE TO DATE: JEREMY
In Season 6, Carrie unexpectedly reunited with her old high school boyfriend Jeremy. They picked up where they left off like they were kissing under the bleachers, and soon they were going all the way, much to Carrie's delight.
The only problem was that Jeremy was only on leave in New York City for a short time from a mental hospital. He found he was more comfortable in a regimented environment, and could never give Carrie the sort of freedom she needed.