Mayer understands why he comes off a little, shall we say, brazen. "Yes, I'm a little jazz-hand-y," Mayer says. "But people forget that bands traditionally have been a little jazz-hand-y. If you have the propensity to be in show business, chances are you're a little jazz-hand-y."

Thus the widely acclaimed guitar virtuoso will tell InStyle all about the lip balm he always takes with him on the road (Kiehl's #1) and will reveal to Cosmopolitan the qualities he looks for in a woman. (For the record: "A person who understands me completely.")

Mayer's quest for a person who understands him completely has led him into entanglements with celebrities like Jennifer Love Hewitt, Jessica Simpson, and Jennifer Aniston. This carousel of high-profile girlfriends is perhaps the reason his reputation as a musician has been eclipsed by a public image that is often summarized by the quaint pejorative "cad." During his time in the paparazzi glare, Mayer became known for giving crews from TMZ what he calls comedic "bits," which he now describes as "completely unconscionable." (For its part, TMZ .com now describes Mayer as a "self-referential 'douchebag.'")

Mayer says his flirtation with the dark side of the media was driven by the same, mysterious compulsion that led him, a few years back, to start dabbling in stand-up comedy. "People ask me, 'Are you going up tonight?' And I say no, and I believe no," Mayer says. "Not that cute little 'I've got the ukelele behind the couch' thing people do on talk shows. I'm really saying I do not want to go up onstage. Next thing you know, my hand is taking the microphone out of the clip. . . .

"I've never done anything because I thought it would look cool. It's always been a pursuit based on a curiosity—never a war-room strategy for my career. And, in fact, given the case history of singer-songwriters, anything other than leaning the side of your head against the bout of your acoustic guitar at the photo shoot is a wild card to people."

After Mayer has ordered his second Campari, I wonder out loud whether that might be the English dance-pop artist Sophie Ellis-Bextor at the next table. "Out here, if you think it's them, it's them," Mayer responds like a seasoned Hollywood macher.