Courtside Cuties! Jack Antonoff and Margaret Qualley Attend Knicks Game

He captured her heart. Margaret Qualley and Jack Antonoff kept their romance under the radar before confirming their engagement in May 2022.

The twosome were first linked in August 2021 following the Maid star’s brief relationships with Pete Davidson and Shia LaBeouf. The Bleachers singer, for his part, previously dated Lena Dunham from 2012 to 2018.

“I mean, we own a dog together. We own a home together, but the marriage thing is a big deal,” the Girls alum told Ellen DeGeneres in 2015, confessing that she and Antonoff had talked about getting married “at some point.”

Us Weekly confirmed the duo’s split in January 2018, months after Dunham reflected on their relationship in a Variety essay. “It’s safe to say that before Jack my life was full of far fewer sights,” she wrote in October 2017. “He showed me the importance of making political statements using your public platform. He showed me the joy of collaboration. He showed me the magic of his home state of New Jersey and turned the butt of my snotty New Yorker jokes into a glimmering fantasyland. I know he does the same for all the artists he produces for, the fans who come to his shows and the recipients of his love. I try and share nicely.”

Two years after their breakup, the Lenny Letter creator revealed it wasn’t “easy” moving on from the musician. “We fell in love when I was really young,” she told Cosmopolitan UK in January 2020. “I was 25. I look back and we had a great ride, we cared for each other, but you know what? We were both starting our careers and that was our true passion. The love you have for someone doesn’t disappear because you don’t have them; it’s just logistically it doesn’t work anymore.”

Dunham called the Grammy winner “a dear friend” despite the end of their romance, adding, “What’s really nice is we don’t try to pretend that we don’t have this history together, but we’re also willing to move forward.”

Antonoff, for his part, went on to use the split as the inspiration for the third Bleachers album, Take The Sadness Out Of Saturday Night. “I was writing for a long time. The early process was, I got out of a relationship,” he recalled to Rolling Stone in June 2021. “I felt an amazing amount of darkness and depression. I fell in there. But the moment it starts to open up and you see a piece of light is a really amazing place to write from.”

He continued, “There’s a lot of desperation in these songs, and I realized, ‘Oh, that’s the same feeling of being from New Jersey, that desperation of wanting out, of I want to break through into another part of my life.’ So that’s when I started to see the framework. And then a really amazing thing happened when the pandemic hit. It was like the final piece of the album, because everything I’m talking about in the songwriting is about sort of dreaming of a next place.”

Two months later, the “Shadow” performer was spotted packing on the PDA with Qualley. The Once Upon a Time in Hollywood actress joked about the “terrifying” experience of meeting Antonoff’s parents in March 2022, telling Another magazine, “[I thought], ‘Please like me, please like me, this is so important, please.'”

After less than one year together, Qualley and Antonoff got engaged. Scroll down to relive the pair’s whirlwind romance: