“I’m sorry, I can’t, don’t hate me” is Berger’s infamous breakup message to Carrie, which he leaves via Post-it, but the struggling writer tipped his hand as a walking red flag much earlier inSex and the Citythan you might think. ThoughCarrie and Big’s tumultuous relationshipis the show’s biggest romantic throughline, theSATCprotagonist dates several other men throughout the series, including Jack Berger. Introduced inSex and the Cityseason 5, episode 5, “Plus One Is the Loneliest Number”, Berger is a self-deprecating writer whom Carrie is instantly smitten with.

After Berger gets out of a failing relationship, he and Carrie begin dating and prove their initial chemistry isn’t a fluke, and they quickly become “the couple you want to be”. However, their honeymoon phase is short-lived, as the success of Carrie’s first book coincides with Berger’s own career failings, and his insecurities come bubbling to the surface. They try to make it work, even recommitting to each other with passionate makeup sex, but the morning after is whenCarrie gets the mother of all breakups. Butan overlooked key detail about Berger’s background spelled doom for the couple.

Carrie and Berger grumpily reading in bed in Sex and the City

Berger Having A Hamptons House Means He Likely Came From Family Money

He Didn’t Have To Earn Anything Himself

It’s not uncommon for Carrie to date affluent men, but when we think about her richestboyfriends inSex and the City, Mr. Big and Aleksandr Petrovsky are the names likeliest to come to mind. Yet Berger has a chic apartment that’s practically a palace by Manhattan standards, is able to buy himself a new motorcycle, and, here’s the kicker — he has a house in the Hamptons. There’sno way he’d be able to afford this luxurious lifestyle solely as the author of one underperforming book.

When he does get dropped by his publisher, Berger’s only concern is his fragile ego, not bills and finances. This all speaks to him having family money.

Berger’s note in Sex and the City

Then there’s the fact that when he does get dropped by his publisher, Berger’s only concern is his fragile ego, not bills and finances. This all speaks to him having family money. Now, that in and of itself isn’t a red flag — who wouldn’t want to be able to pursue their art with the backing of a cushy nest egg?

But this would mean that Berger has never had to earn anything for himself. Whereas Big also comes from an affluent background, he’s a successful financier in his own right. ButBerger has never seen success, and when that’s contrasted with his girlfriend’s career boon, it sets off a toxic chain reaction.

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Carrie Buying Berger The Prada Shirt Makes Him Envious Because She Earned Her Success Herself

Everything Goes Downhill From There

Cracks were already beginning to form in Carrie and Berger’s relationship, but a certainfabulousshirt pushes things over the edge. When Carrie gets a massive advance after her book sells in France, she wants to celebrate her good news by buying Berger a Prada shirt he was admiring. Things instantly sour from there, and by the end of the next episode, Berger’s sorry, he can’t, don’t hate him.

It’s very telling thatBerger was visibly more upset when Carrie showed him her $25,000 check than when he thought she couldn’t afford the shirt. Of course, it’s sympathetic that it would sting to see your partner’s writing career flourish while yours is going up in flames, but if the Berger has family money theory is true, his issues are deeper than ego.

Instead of admiring Carrie, he punishes her for it, and it’s due to his insecurities that the two never recover.

Carrie is entirely a success of her own making, from moving to New York as a broke 22-year-old to earning a five-figure advance on a book. Even with all his advantages, Berger’s never been able to accomplish anything close to that. Instead of admiring Carrie, he punishes her for it, and it’s due to his insecurities that the two never recover.

Berger Never Learned To Communicate In His Relationships

Hence, The Infamous Post-It

Berger seemingly expecting to have everything handed to him on a silver platter apparently extends to his relationship. Whenever anything gets tense or uncomfortable,his response is to be passive-aggressive, lash out, or deny there’s a problem. He’s beyond aggressive at his ex’s voicemail,he insults Carrie after her (extremely valid) scrunchie comment, and when he and Carrie get snippy with each other, rather than sit down and have an honest conversation about their feelings, he does the “Hollywood kiss bit”.

Berger’s friend Billy, who (deservedly) bears the brunt of Carrie’s anger at the club is played by Michael Showalter, who went on to direct several popular films, including the romantic comediesThe Big SickandThe Idea of You.

This all culminates in Berger breaking up with Carrie on a Post-it. Honestly, he was right to end it; their relationship wasn’t working. But when Carrie berates his friends about Berger’s callousness,she’s absolutely right that she deserved better — not just in the breakup, but in the entire relationship. We’ll never know why Berger is the way he is, though I can’t help but wonder if theSex and the Citycharacter is so privileged that he’s never had to deal with a real problem himself.