Sex And The City’s 12 Worst Relationships

Sex and the City offered viewers a window into the lives and relationships of Carrie, Samantha, Charlotte, and Miranda. Of course, there were some great relationships, some awful ones, and plenty that fell somewhere in between. There are almost too many unsuccessful relationships to choose from, but here are a few of the worst ones. Some were jerks, some lied, some cheated, some had problems in the bedroom, but all of them were wrong for the women they were dating for one reason or another. Here are the 12 absolute worst relationships in Sex and the City:

12. Kevin, the Lawyer

Kevin was a lawyer who was always aggressive. Unfortunately, he couldn’t seem to keep his aggression in the courtroom. While Miranda was with Kevin, she was always on edge, waiting for him to blow up at her or someone else. She liked his bossiness in bed, but hated it in life. She kept making excuses for him, saying that things would improve when his work life improved. When he was finally made full partner at his law firm, she thought he would be happy, but that wasn’t the case. Miranda finally decided that enough was enough, and she broke it off with him. Thank God!

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11. Mike

Charlotte’s problem with Mike was that he wasn’t circumcised. She went on a rant about it with her friends after one of their dates, using many colorful (and highly offensive) analogies. She went out with him again, but said goodbye to him at the door instead of going upstairs with him. He said that she wasn’t the first woman to be uncomfortable with the fact that he wasn’t circumcised, and told her that he had decided to get surgery. She was thrilled and said that she would wait for him. Wanting someone to surgically alter a part of their body in order to be with them is pretty shallow, so the fact that he dumped her after the surgery was just icing on the already awful cake.

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10. Jim, the Ex

Jim makes the list for being a bad match for both Carrie and Miranda. When Miranda met Jim, Carrie warned her that he was a jerk to her after they broke up, but Miranda ignored her warning. Jim seemed nice when he first interacted with Miranda, but for their second date, Miranda insisted that Carrie join them for a drink and that’s when things got mean. Jim got snarky, and started insulting Carrie repeatedly in front of Miranda, who then dumped him at the table. Jim showed his true colors and started yelling at her too. Miranda finally understood that Jim was a total jerk.

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9. Bill Kelley

Bill seemed like a nice enough guy. His penchant for golden showers was a bit out of the ordinary, but was not the reason he landed on this list. The thing that did land him on the list was his decision to break up with Carrie because her writing a sex column could potentially compromise his career. Considering that he wanted Carrie to relieve herself on him makes the reason for him breaking up with her kind of hypocritical.

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8. Dominic, Samantha’s First Love

Samantha doesn’t fall in love often, but Dominic was her first. He dumped her for a supermodel who he later married, and it took her a long time to get over him. When she ran into him again after his divorce, she decided that she would make him want her and then ditch him before having sex. When the moment came, she decided to have sex with him before dumping him but, after having sex, she decided that “her desire for revenge wasn’t as strong as her desire for Dominic.” In the morning, however, Dominic broke up with her, telling her that he’s going back to his ex wife, the supermodel. He dumped her twice for the same woman. She never did get her revenge and he just ended up hurting her again.

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7. Ned, the Widower

Charlotte met Ned at a cemetery after attending a funeral. Not exactly a fairy tale setting, but Charlotte still thought it was hopelessly romantic when they met after her hat blew onto his wife’s grave. Their first date went well but, while he was paying, she saw a picture of his wife in his wallet. He got emotional, and this somehow led to them having sex. She felt as though she was helping him to move on. He invited her to his wife’s memorial and she was very touched. When she arrived she discovered that he had invited three other women he was seeing. In addition to not being very smart (who invites four women you are sleeping with to the same event, let alone to a memorial service for your wife?), using his grief as a tool to pick up women was a bit disturbing.

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6. Patrick Casey

Carrie probably should have listened to Patrick when he told her he’s in AA and not supposed to start any new relationships in the first year of recovery, but they jumped headfirst into a relationship anyway. After Patrick had sex with Carrie, she quickly became his drug of choice. After a few sex-filled days, he proclaimed his love for her after only a week and a half of dating. All of this was too much for Carrie, and when she asked to slow things down a bit and go a few days without seeing each other, he showed up on her doorstep the very same night, drunk as a skunk. He screamed and swore at her outside her window, getting naked and begging her to have sex with him. Needless to say, things didn’t work out between them.

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5. Skipper Johnston

Skipper made this list not because he was bad for Miranda, but because she was bad for him. Skipper was madly in love with Miranda and she didn’t feel the same way about him. Long after they broke up, she saw him with another woman and suddenly found him more attractive. She called him up. He answered the phone despite the fact that he was currently having sex with his girlfriend and then broke up with her the second he hung up the phone so that he could get back together with Miranda. This lead to the line, “You’re breaking up with me while you’re still inside of me?” That seems to be plenty of proof that this relationship was not healthy. After they go out and sleep together, Miranda let Skipper know that it was just a one-time thing for her, and he was devastated once again.

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4. Trey MacDougal

Charlotte met Trey when she tripped and fell in front of the taxi he was in. It was another cute meeting that seemed meant to be. She was convinced that Trey was perfect for her, and their relationship went from zero to married in no time. It didn’t take long for the flaws to start to pop up though and for viewers to see that this relationship was not going to be Charlotte’s happily ever after. From their problems in the bedroom to their interactions with his family to their different opinions about having children, there were just too many things going wrong in this marriage for it to last. After Charlotte was caught kissing the gardener, they separated. They eventually get back together and resolved some of their issues, but there were too many problems they couldn’t fix and they eventually got a divorce.

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3. Jack Berger

It wasn’t just the breakup that was awful. Things between Carrie and Jack Berger were always far from perfect. They argued so frequently that they had to come up with a funny “bit” to do when they were annoying each other. He was bitter, cranky, angry, very intimidated by her success with her writing career and very touchy about his own writing. You would think that a relationship filled with arguments might at least be passionate in the bedroom, but that was the one area where they didn’t have fireworks. Things were rocky for quite a while, but Carrie kept trying to fix things. If only Carrie had ended things before he had the chance to break up with her on that Post-It, sneaking out in the middle of the night after claiming that he wanted to try to work things out.

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2. Richard Wright

Samantha and Richard both loved sleeping around, but tried to have a monogamous relationship. Samantha caught him cheating on her, gave him a second chance, and then realized she could never trust him again. She slept with him one more time much later on, cheating on someone she really cared about, and immediately knew that it was a mistake and that she didn’t love Richard anymore. Thankfully, after that, he was completely out of her system.

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1. Aleksandr Petrovsky

Aleksandr and Carrie dated until the series finale, and it looked as though she might end up with him. Some viewers supported this, and others were screaming at the television, begging her not to make such an enormous mistake. As Carrie said, she had nothing in common with Aleksandr. They had communication issues; he didn’t include her in many parts of his life; and he was very set in his ways. Still, she left her home, her friends, and her job to move to Paris with him. Even then, he prioritized his work over their relationship and she was miserable. When Carrie said, “sometimes there’s not enough time in a night for both your worlds,” this seemed to be true about their entire relationship, not just one night. During their final argument, Aleksandr slapped her, and she quickly got herself out of Paris and out of that relationship.