Nat Wolff's Romantic History Includes Miranda Cosgrove, Margaret Qualley, and Grace Van Patten

Wolff and Cosgrove were rumoured to have dated at the height of both of their Nickelodeon careers in 2008. But Cosgrove told TigerBeat in 2010 that she and Wolff were "only friends." However, in a 2011 interview with Seventeen (via People), Cosgrove opened up about going through a rough breakup. While she didn't name Wolff specifically, many speculated her heartbreak was due to their reported split.

"I've only had one serious boyfriend, but we dated for three years," the "iCarly" actor said at the time. "We broke up not that long ago. He's the one guy I really, really liked. People say they have that one person they never forget — I feel like that. Even though we don't talk too much anymore, he'll be the one who got away."

Wolff and Waterhouse sparked romance rumours in 2015 after they were photographed at a The Strokes concert in London. The following night, the actor was spotted sneaking out of Waterhouse's home in photos obtained by the Daily Mail. However, their romance appeared to be short-lived as they split after a few weeks, according to Elle.

Wolff and Thorne were the talk of the town when they were spotted sharing a hug after dining together in Los Angeles in February 2017, per the Daily Mail. However, it's still unclear if they were romantically involved or simply hanging out as friends.