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Jack Berger’s breakup method cemented him in history as one of Carrie Bradshaw’s worst boyfriends. His breakup strategy was by far the worst seen on Sex and the City. To be honest, Berger was not a great guy from the start. Carrie ignored a ton of red flags from the very beginning of the relationship if you think about it. It really was no surprise that Berger behaved so poorly.

Berger was in a relationship when Carrie met him

Carrie and Berger first met at the office of their mutual publisher. Carrie, instantly intrigued by Berger, agreed to spend some time learning the ropes of publishing from him. Berger, instead of discussing work, seemed to take Carrie on a date. That was until she asked him to join her at her launch party.

Ron Livingston attends the 'Sex and the CIty' season 5 premiere
Ron Livingston portrayed Jack Berger in ‘Sex and the City’ | Ron Galella/Ron Galella Collection via Getty Images

Finally, Berger fessed up to having a live-in girlfriend. Charlotte York insisted he was a jerk for not mentioning his relationship status, but Carrie made excuses for him. In the end, Charlotte was right. Berger flirted with Carrie and had no intention of mentioning his girlfriend unless he absolutely had to. He was a jerk at the start of their relationship, and he was a jerk at the end of it.

He wasn’t over his ex when he and Carrie first got together

Before Berger got incredibly insecure about Carrie’s success, fans were supposed to believe he was a good fit for Carrie. After all, they were both writers. Their common career path couldn’t overshadow the fact that Berger was bringing a lot of baggage into their relationship. He absolutely wasn’t over Lauren, his ex-girlfriend, when things started heating up with Carrie. 

Upon Carrie’s first visit to Berger’s apartment, he mentioned his ex-girlfriend multiple times. He then gave his answering machine a double middle finger when she left a perfectly neutral message. Sure, hearing from your ex is rarely fun, but his visceral reaction to her mention proved he absolutely wasn’t over the relationship.

Berger was incredibly threatened by Carrie’s success

Berger was the one who ended his relationship with Carrie via a Post-It note, but that’s honestly not the worst thing he did during his brief tenure on Sex and the City. Berger’s worst offense was his insecurity about Carrie’s success. He simply could not stand that Carrie’s book was a success while his floundered.

Sarah Jessica Parker as Carrie Bradshaw
Sarah Jessica Parker as Carrie Bradshaw | Arnaldo Magnani/Getty Images

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While it’s understandable that Berger would be bummed about his career setback, he could have still been supportive of Carrie. Carrie tried especially hard to keep her success low key to make him feel better. Add in the fact that he was overly sensitive about even minor criticism, and you have a ton of red flags that Carrie actively ignored.