Jack Antonoff had several high-profile relationships before his three-year marriage to Margaret Qualley.
“He’d often prefer for things to be done the way he thought was best, and Margaret didn’t always feel like her perspective was being heard or given the same weight.”
“Communication was definitely a challenge between him and Margaret,” the insider added.
Here is a look back at all the women the musician dated before his notoriously private romance with the actress.
Antonoff and Scarlett Johansson dated for two years while attending Manhattan’s Professional Children’s School in New York City together.
“When we were in high school, Jack was absolutely obsessed with her, and she broke his heart,” a former classmate of theirs told The Post at the time.
“They broke up shortly after graduation . . . She got swept up in the Hollywood scene.”
The Oscar nominee is now married to “Saturday Night Live” star Colin Jost.
The Bleachers frontman dated Lena Dunham from 2012 to 2017.
The former couple was initially set up on a blind date by comedian Mike Birbiglia and Jack’s sister, Rachel Antonoff.
Jack and the “Girls” creator instantly hit it off and began dating shortly after.
However, in Dunham’s 2026 memoir, “Famesick,” she detailed how their relationship began to crumble after she got a hysterectomy in 2017.
In the book, she confessed to cheating on Jack with an old flame.
She went on to marry musician Luis Felber in September 2021.
The exes risked an awkward run-in at Taylor Swift and Travis Kelce’s star-studded wedding festivities over the Fourth of July weekend.
They were both spotted arriving at Madison Square Garden for the pop star’s rehearsal dinner on July 2.
Just weeks after his breakup from Dunham, rumors began to swirl that the songwriter was dating Lorde.
Jack, notably, produced and co-wrote Lorde’s critically acclaimed sophomore album “Melodrama” in 2017.
Both musicians admitted to working closely over 18 months, recording much of the album at his private “Rough Customer” studio in Brooklyn Heights.
Dunham also touched on Lorde and Jack’s “closeness” in “Famesick,” claiming that she once returned home only to find Jack in “the recording studio in our apartment, where he was ensconced with a teen pop star I was too oblivious to be jealous of.”
Though Dunham didn’t name the singer in her novel, Lorde was between 19 and 20 in 2017 while Jack was 33.
Dunham also wrote that Jack spent his time “locked in a room with a teen pop star whose needs seemed as massive and complex as my own, and who called me ‘Aunt Lena’ when I hobbled into the kitchen with my walker to grab another bottle of green tea.”
However, Lorde and Jack both maintained that they were just close friends.
“Normally i would never address rumors but i resent having the most important friendships and working relationships in my life reduced to dumb hetero normative gossip,” he wrote in a since-deleted tweet in January 2018.
“Those relationships are deeply important and sacred. with that said, im not seeing anyone. lol.”
The next month, the “Royals” songstress shared a similar sentiment in an Instagram Live, per E! News.
“Guys… Jack and I are not dating, for the last time. I love him, he’s awesome. But we’re not dating! Please!” she said.
Despite their denials, the pair’s frequent joint outings did not help silence the rumors of a secret relationship.
The music producer was also romantically linked to model Carlotta Kohl in 2018.
The duo first sparked dating speculation in March when they were pictured cuddling up to one another while sitting courtside at a New York Knicks game.
While they generally kept a low profile, the pair made a notable red-carpet appearance at the 2021 Grammy Awards, where Jack took home the Album of the Year award for his work on Swift’s “Folklore.”
It remains unclear when Jack and Kohl parted ways.
Qualley and Jack were romantically linked for the first time in August 2021 when they were seen kissing on a bridge in Brooklyn during a low-key date.
They made their romance official in March 2022 when they attended the AFI Awards Luncheon together.
Two months later, news of the pair’s engagement broke when the “Maid” star flashed her stunning diamond sparkler — estimated at nearly $100,000 — at the Cannes Film Festival.
She officially confirmed the news when she shared a series of snaps to her Instagram.
On Aug. 19, 2023, the couple officially said “I do” in an intimate ceremony at Parker’s Garage on Long Beach Island, New Jersey.
The nuptials featured several A-list guests including Swift, Channing Tatum, Zoë Kravitz and Cara Delevingne, along with Margaret’s mother, Andie MacDowell, and sister Rainey Qualley.
By July 2026, several signs pointed to a split between the couple.
Jack attended Swift’s wedding on July 3 without his estranged wife, before fans realized they hadn’t been publicly spotted together since February.
Additionally, eagle-eyed fans noticed that the Lana Del Rey x Bleachers track about the “Substance” star titled “Margaret” wasn’t included in the band’s setlist for their “Shadow of the City” tour.
