Jack Antonoff Dated Scarlett Johansson in High School and You Have to See Their Haircuts

Congrats are in order for Jack Antonoff! The Bleachers lead singer is currently engaged to actress Margaret Qualley. The pair got together in 2021 and given that dazzling rock currently crowning her finger, it's safe to say that things are going pretty well.

But before Jack and Margaret walk down the aisle (no deets on that yet), let’s take a look at all the other ladies that Jack has previously romanced. Spoiler alert: The Maid star isn’t the only lady in Hollywood who he's gone steady with.

Keep scrolling for a rundown of all of Jack Antonoff’s known romantic relationships.

Truthfully, this might be Jack's most surprising relationship!

Per Instyle, Jack and Black Widow star Scarlett Johansson both attended New York’s Professional Children’s School for high school, which is a prep school for children who aspire to work as actors and dancers. They dated for about a year and even went to their prom together. Their retro haircuts in the photo above say it all!

Sadly, they called it quits after graduation because she “got swept up in the Hollywood scene," per Page Six.

How did Jack did take the breakup? He didn't share too many details. But interestingly enough, he penned a pretty angsty song dubbed "Better Love" in 2005 for his then-band Steel Train. With lyrics like, "Scars are in her name / And she scars me with blame / Hey Scarlett, you're not the same," we have an inkling that Jack may have had some trouble getting over her.

Actress Alia Shawkat, who's well-known for her role in Arrested Development, was rumored to have been in a relationship with Jack Antonoff in 2009 and 2010, per Ranker. Sadly, there is very little photographic evidence of their courtship.

However, it seems they ended things on good terms as years later, Alia starred alongside Jack in The Bleacher's music video for "Don't Take the Money." The video was actually directed by Lena Dunham, which brings us to another one of Jack's former lovers.

Jack's relationship with Girls star Lena Dunham was definitely his most public relationship. Per People, they were set up on a blind date in 2012 by Jack's sister Rachel and comedian Mike Birbiglia.

Fortunately, they hit it off and Jack started sharing everything about himself with her. As he told New York magazine in 2014, “When you really like someone, you want them to know everything about you."

They lived together in her Brooklyn apartment throughout the course of their six years together.

They even sparked engagement rumors, but there was never a ring. The couple's breakup was reported to be amicable per People.

After things ended with Lena, Jack got right back in the dating game and linked up with model Carlotta Kohl. Very little is known about their relationship, but they were first spotted at a New York Knicks game that year in March, per Amo Mama.

It is believed they connected right after Carlotta appeared on St. Vincent's album "Masseduction," which St. Vincent had co-produced with Jack.

Finally, these love birds!

Margaret Qualley and Jack Antonoff first sparked dating rumors in August 2021 when they were spotted showing off some major PDA while hanging out in New York City. Things remained up in the air until March of this year when they went Instagram official. And as of late May, a source had confirmed to People that they are in fact engaged. Best of luck to you two!