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The four ladies of Sex and the City got their happy endings when the show wrapped its sixth season. Miranda Hobbs settled into life in Brooklyn with Steve Brady. Charlotte York’s Park Avenue dreams came true with Harry Goldenblatt. Samantha Jones left New York to support her man, Smith Jared, in California, and Carrie Bradshaw and Mr. Big finally made their relationship work. It took a lot to get to those happy endings, though. The ladies dated some genuinely horrible men along the way. So who tops the list as the absolute worst boyfriends?

Jack Berger was incredibly insecure

Fans had really high hopes for Jack Berger when he was first introduced in season 5. Jack was cute and smart. He even had a career in common with Carrie. In retrospect, fans probably should have seen the writing on the wall. Carrie had already had one disastrous relationship with a fellow writer, and this one didn’t fare any better.

Jack was incredibly insecure and couldn’t deal with Carrie’s success. He couldn’t take even the most basic of criticism, and he sulked a lot. Jack cemented his position as the worst boyfriend of the entire series when he broke up with Carrie via a Post-It note.  Liz Tuccilo, a writer for the series, told Elle that the Post-It storyline came about organically in the writing room. She agreed that it was a truly terrible way for Berger to put an end to his relationship with Carrie.

Richard Wright really didn’t need to behave the way he did

Samantha wasn’t initially interested in a relationship. She was perfectly fine, living her life as a single woman on the hunt for a new man every night. Then Richard Wright came into the picture. Samantha resisted his more romantic advances, initially, but he persisted. He finally got what he wanted. He got Samantha to open up to him and enter a committed relationship; then, he cheated on her.

Richard makes the list of the worst Sex and the City boyfriends because his behavior was completely inexplicable. Why bother trying to lock down a serious relationship with someone who is so resistant to it, just to turn around and cheat? None of it made any sense, and he’s one of the most hated men ever to be featured on the series.

Wade Adams was not the right guy to commit a crime with

Wade Adams seemed like the perfect guy to have a summer fling with. He was cute, fun, and impulsive. While he was never going to a be a long-term match for Carrie, he was just the type of fun she needed after her relationship with Aidan went up in smoke. Carrie was even okay with the fact that Wade lived with his parents, and was immature beyond belief. Fans would have been fine with Wade if he hadn’t turned into a literal snitch.

Together, they decide to indulge in a little smoke while Wade’s parents were out one afternoon. Not only did they get caught, but Wade blamed the entire incident on Carrie, just so he didn’t have to move out of his parents’ apartment. It wasn’t even Carrie’s pot! Marijuana may be legal in several parts of the country now, but back in the early 2000s, it was very much illegal in New York City.

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