So if money isn't doing it, and Romney's personality isn't winning him converts, what's left?
The debates. They start in early October, then it's bam, bam, bam: 10/3, 10/11 (veep), 10/16, and 10/22. They will present Romney with his last chance to gain points from Obama.
However, he can't score points by playing it safe. If he tries to be nice and gracious and not touch Obama like he touched Gov. Rick Perry in one of those early-season debates, he might earn brownie points, but Obama will remain unscathed.
So he has to attack.
But remember, people think he's a dick. So Romney has to attack in a manner that doesn't reinforce the narrative that he's a dick. And who really thinks Romney has the chops to pull that off? He can't interact with NASCAR fans or picnicking ladies or British prime ministers without coming off as a dick. He's now supposed to deftly attack—with a convincing smile—the guy who is standing between him and his birthright presidency?
Meanwhile, Obama can play it safe. He is winning. He can be gracious and accommodating, all the while rising above any nastiness with presidential bearing. He doesn't need to win these debates as much as not lose them, and that makes his job so much easier.
It seems pretty clear cut. If Romney plays it safe, he continues to lose. He has to throw that Hail Mary. But by going on the offensive, he'll remind people that they think he's a dick. Because he is.
It's going to be brilliant.