I have some long comments on the "Liberaltarians" craze that's sweeping the nation over at Tapped, but as a slightly more superficial observation, an alliance between liberals and libertarians is going to be hampered by our fundamentally different methods of understanding our movements. Every libertarian who's written about the possibilities for a grand alliance has talked about Hayek and Rawls. On the other side of the divide, both Kevin and I critiqued the concept on the level of policy disagreement -- neither of us refer back to treatises.
That's not a coincidence: Libertarians, who're something of an ideological movement without much hope for political power, tend to spend a lot of time puzzling through the theory and philosophy of their ideas. Liberals, who're something of a political movement without much hope for ideological purity, tend to think through policies and outcomes. Because of that, the libertarians see a lot of philosophical common ground, which to them suggest important points of similarity, while liberals see a lot of policy disagreements, which to them suggest near-irreconcilable differences.
As example, Will Wilkinson thinks that Social Security privatization is more Rawlsian than the current system, and this strikes Will as the sort of argumentative approach that liberals will find compelling. That's wrong. It's the sort of argumentative approach Will Wilkinson would find compelling. Liberals could discover a lost Rawlsian text called "Universal Health Care Is A Really Bad Idea And Liberals Shouldn't Support It," and no one would care, save for those who'd have to stop naming Rawls as an intellectual inspiration. This difference actually strikes me as pretty fundamental, and makes an enduring rapprochement seem somewhat unlikely.
Anyway, read the Tapped post.