The international DJ detailed two separate times he played his music for Rihanna in his August cover story of GQ, and both interactions were cringe worthy.
"I played her 'Lean On,'" he said. "She was like, 'I don't do house music.' I face-palmed so hard on that one."
But the DJ was determined (and also "contact high") when he attempted to impress the pop star a second time.
"Another time I had a session with her, and Future was also invited... Future played her, like, 700 songs. It was four in the morning. Finally, I was like, 'Yo, G, I'm leaving unless you let me play her a song.' So I played her a song. And she was like, 'This sounds like a reggae song at an airport.'"
"I was like, 'I'm gonna go kill myself,'" he said, laughing off the embarrassment.
Still, the DJ isn't giving up total hope, saying, "I just want her on a Major Lazer song. She's like the one artist that we can't ever get."
The topic of Rihanna came about when Diplo was asked what he brings to the studio when he's working on music with other artists.
"I'm not good at anything specifically," he said candidly. "You know, I was editing this song earlier [plays sounds on laptop], and the longer I spent on here, the more I felt like, God, this sucks. I don't want to sit here going through presets. I'm the guy who's like, 'OK, Mr Eazi's in town. I'm trying to do an Afro-beat song. And maybe we'll play it for Rihanna or whatever.' But actually sitting here putting drums in? That's f-cking wack.