John Mayer is fast becoming his generation's Warren Beatty.

Mayer was out last week with pop star girlfriend Katy Perry enjoying time alone in the Southern California paradise of Santa Barbara.

But Perry is not the first star he has spirited off to a romantic getaway. Jennifer Love Hewitt, Jessica Simpson, Minka Kelly, Jennifer Aniston and Taylor Swift -- to name only those we know of -- have all been seen on the strummer's arm.

PHOTOS: John Mayer and his famous girlfriends.

But why?

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He's cute, but he's no Brad Pitt. He's had hit songs, but he's no Justin Bieber. He's rich, but he's not as rich as half the gals he dates.

So what is it?


L.A-based life and career strategist, Suzannah Galland posits that “women of fame, often find themselves isolated from the values they’ve grown up with. Mayer will have no problem attracting women who are so far off their ground, that touching ground for them is like touching gold.”

Wendy Walsh, author of the forthcoming book "The 30-Day Love Detox," told FOX411’s Pop Tarts column that Mayer "fits the bad-boy persona that turns so many women on. When a man has a history of many short-term relationships, and then focuses his attention on a new woman, she might believe the fallacy that she will be the one to change him, to turn him into a long term committed boyfriend.”

Walsh also offered words of wisdom to Perry in particular: "Run!"

But so far she's not, and Hollywood matchmaker Matt Titus thinks he knows why. Titus says a certain gang mentality is at work, and that once one or two Hollywood “it” girls have gone there, it makes a man all that more attractive.

“It is mass appeal,” Titus explained. “He doesn’t have to try to get attention, it comes to him.”

Of course dating Mayer has never yet proven to be a long-term proposition. Or even a reliable short-term one. In 2010, years after he and Simpson split, Mayer revealed intimate details about their relationship to Playboy magazine.

“That girl, for me, is a drug. And drugs aren’t good for you if you do lots of them,” he told the men’s magazine. “Yeah, that girl is like crack cocaine to me… Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm.”

Mayer then voluntarily removed himself from Twitter in September of the same year following a swirl of rumors that he was dumped by the very private Aniston for tweeting too much.

And in her song “Dear John,” reportedly about her brief Mayer liaison, Swift crooned about the romance with lines like “Don't you think I was too young to be messed with? The girl in the dress cried the whole way home” and “All the girls that you've run dry have tired, lifeless eyes 'Cause you've burn them out.”

Not only does Mr. Mayer seem to fare well with the ladies, he seemingly manages to mesmerize into morphing into his style. In the recent Santa Barbara sighting, Perry ditched her famous florescent getups with equally bright makeup for Mayer’s ultra laid-back approach. The two wore almost matching floppy hats, low key hipster pants and loose-fitting jackets. Similarly, Simpson parted ways with her bouncy blonde locks to become a boho brunette when she started dating the rock musician, going from career go-getter to groupie rocker chic as she bounced from dive bar to dive bar by his side.

“Why wouldn't they want to dress like him?" Titus says. "John is prettier and hipper than everyone he dates."

Perry's record label may want to take note, lest she follow up her multi-platinum power pop with acoustic love songs featuring you-know-who on guitar.