Speaking on Late Night with Jimmy Fallon, the singer revealed that he gave a rendition of a page from Fifty Shades of Grey, which is soon to be made into a film.
Mayer recalled: "I was trying to impress her, and she had [the book] on her Kindle. And so I said, 'I'm going to sing it to you.' So I sang her one of the pages of Fifty Shades of Grey.
"She fell to the ground... laughing."
Fifty Shades of Grey - written by EL James and originally conceived as a piece of Twilight fan fiction - will be produced for the big screen by Universal and Focus Features.
The 34-year-old - who has previously dated women including Jessica Simpson and Jennifer Aniston - also revealed that he was a fan of dating show The Bachelor last week on The Ellen Show.
"I don't even feel like it's my fault for liking it. It's not a guilty pleasure. It's designed to be a pleasure," he said.
"It's one of those things where I would waste their time taking a meeting, just so I could hear more about it. Ultimately, I'd say no. But I would just have to take the meeting."
Watch the video to 'Shadow Days' by John Mayer below: