Diplo’s dating history, revealed: he’s had relationships with M.I.A. and Katy Perry and was linked to Madonna and Kate Hudson – but which rapper claims she had sex with him when she was just 17?

Jan 9 , 2025

Diplo and Madonna, who he’s been romantically linked to. Photo: @diplo/Instagram

Diplo was once ranked third best in bed by his ex Katy Perry, behind Orlando Bloom and John Mayer; but he’s also run into legal troubles, with women accusing him of sexual misconduct

Diplo rang in the New Year with a dash of honesty. The American DJ and producer had no qualms about admitting he was under the influence of psychedelics when he appeared on CNN’s New Year’s Eve Live show, hosted by Andy Cohen and Anderson Cooper.

The 46-year-old casually revealed that he “did some [LSD] on the helicopter on the way here” and insisted it was a “light trip”, thanks to “microdosing” – but mentioned as a side note that he “might have macrodosed earlier”. Following the quick interview, he performed at the Avalon Hollywood nightclub.

Besides his hard-partying ways, another aspect of Diplo’s life that has interested fans is his dating history. Regarding his sexuality, he once told Emily Ratajkowski on her High Low podcast that he’s “not not gay” but “more of a vibe guy”.

So who are the romantic partners with whom the multi-Grammy winner – real name Thomas Wesley Pentz – has vibed?

Diplo’s longest public relationship was with M.I.A.

Diplo and M.I.A. dated for five years. Photo: @diplo/Instagram

One of Diplo’s first known relationships was with British rapper M.I.A. The two were reportedly together from 2003 to 2008, during which time they collaborated extensively. However, their split was acrimonious, with him accusing her of “glamorising terrorism” in 2011, according to WWD and her telling Rolling Stone that he was “jealous” of her success. They’ve since worked together again.

He has two baby mamas

Diplo fathered his first child, son Lockett, with event-planner girlfriend Kathryn Lockhart in 2010. Four years later they welcomed their second son, Lazer, but were no longer a couple.