I think this nails, for me, that particular scene best. If the whole movie had been an out-and-out farcical comedy, then it would've worked. It came across more as 'Look at how Woody I can act' and was completely out of tune with the rest of the flick. Allen and Eisenberg's public and movie personas are so far apart - The Social Network was so good/popular/Zeitgeist it set the tone (and typecast, somewhat) a successful start to a career - to fight against that with performances like this is possible if you're a very good/popular actor, and the jury is still out as to whether he is.
Also, back to your point; someone who's a total misfit and rarely/never been intimate with a woman would act a lot less comfortable than someone who's average-to-good looking and probably has.
One last point; them arguing over whether to go ahead or not was very good writing.
Yeah, well, you know, that's just, like, your opinion, man.
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