Appeared in: Season 5, episode 5, 8; season 6, episodes 1-6
Jack Berger had a lot of things going for him. He had a good sense of humor, possessed boyish good looks, and was a writer, just like Carrie. However, he was also passive-aggressive, insecure, had issues with his ex-girlfriend, and was extremely jealous of Carrie's success.
He also broke up with her in perhaps the worst way possible, on a Post-it note, with three sentences: "I'm sorry. I can't. Don't hate me."
Speaking for "Sex and the City" fans everywhere, we do hate you, Berger.