Can Britney Spears ever really make it work with a normal Joe?

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Despite years of up-and-down behavior, Britney Spears remains one of the biggest pop stars in the world. And while she could date basically any single guy in Hollywood, Spears instead has a history of going for a normal Joe, like her former back-up dancer husband Kevin Federline, and kind of like her ex-fiance, agent Jason Trawick.

Now it looks like history is repeating itself -- again -- as it’s being reported Britney is going out with a guy named David, an ordinary, 27-year old-dude who works for a law firm doing ‘field research.’

Now there is nothing inherently wrong with celebrity/civilian couples. Look at Matt Damon and Luciana Baroso, or Alec Baldwin and Hilaria Thomas, for examples of how great it can all work out.

But Brit’s track record of falling for the guy next door hasn’t worked out as well.

So should Spears try again with regular folk, or is Brit’s lifestyle -- and bank account -- so other-worldly that only another superstar could understand?

“I admire the fact that Britney is dating a regular guy,” said Patrick Carone, the executive editor at Maxim Magazine. “[But] while this is admirable, I just don’t know if it’s the kind of thing that works in the real world.”

Carone also wondered, aside from the income disparity, if the gender dynamic might prove to be a problem.

“Even with us regular people, a lot of times, unfortunately, if the woman, you know, makes more money than the guy, [it's a problem] just because there’s all these deep set standards of the man is supposed to be the one who makes the money,” Carone said. “Can you imagine dating a woman and not just financially she’s in charge but everywhere you go, everything you do, every little bit of attention is all focused on her? I mean that’s got to be emasculating to some degree, even to the most, you know, confident self-assured guy.”

But Chloe Melas, senior reporter at, disagrees.

“I don’t think there’s a double standard when it comes to gender in Hollywood,” she said, adding Spears has dated the famous and non-famous alike over the years. “She has dated everyone from agents like Jason Trawick, to Justin Timberlake who was a mega pop star, and she even dated a guy who was a paparazzi who followed her around for weeks and she fell in love with him.  She even married her best friend Jason Alexander for just two days.  So Britney it doesn’t matter who it is.  She falls in love and she falls in love fast."

Both Melas and Carone agreed Spears would probably be better off this time around with an established off camera Hollywood type.

“Maybe kind of like a rich record producer guy,” said Carone.

“Many people believe that Jason Trawick was very good for Britney because he understands the business of being a celebrity,” Melas said. “He was a Hollywood agent for a living, and Britney Spears would probably be better off dating someone who understands what it’s like to live in the spotlight.”