The Star-Studded List of Jack Antonoff's Exes Before Margaret Qualley

Songwriter and frequent Taylor Swift collaborator Jack Antonoff dated a series of actresses and models before finding love with future wife Margaret Qualley.

One of Jack’s most high-profile relationships was with Girls star Lena Dunham, who – despite dating for more than five years – had no plans of tying the knot until gay marriage was legalized. However, upon the Supreme Court’s June 2015 ruling, which made it legal for same-sex couples to wed, Lena quickly realized that she and Jack were not on the same page.

“As soon as Jack woke up [that day], I informed him that he ‘better not make a fool out of me,’ followed by a quick ‘LOL,’ and then, ‘But seriously. I’m going to look like a real idiot if we just sit here like losers and keep dating.’ Then I tweeted, ‘[Jack Antonoff] get on it, yo,’ followed by my immediate and all-consuming regret,” she wrote in a New Yorker essay the following month. “Jack didn’t text back, which is entirely unlike him, and it wasn’t until I got home and looked him in the eye that I realized just how little the concept of marriage had been on his mind.”

The couple ultimately called it quits in January 2018, but Jack didn’t immediately settle down with the Once Upon a Time … in Hollywood actress.