Am I only allowed one pick? Or can I meet the person, then excuse myself to the bathroom, climb out the window and then pick another since the drink / dinner was never fullfilled to completion, thus giving me an 'out' and a way to circumvent your "rules". 

Someone who wouldn't mind that I'm having water.

This is reminding me of... William Shatner has a web series called "Brown Bag Testing" where he talks to someone and they drink a mystery wine and that person uses their area of expertise to describe it (a film guy explains in special effects terms, a bodybuilder discusses it in bodybuilding terms, etc).  it's actually a neat little way to look into how their minds work.

It's a cute idea.  Shatner gets this reputation as being kind of self-centered and in love with his own voice or whatever but recently (maybe because of this, I dunno) he's been doing docs and my mental picture of him is him listening to other people.  Which is what creative types (writers, actors) should be doing anyway, taking it all in.

William Shatner has a web series

What was that TVshow Shatner had where he had invited specific guests and just shoot the bull with them for 1/2 hour?

I'd get a beer with Larry David and Ricky Gervais, both of who are polar opposites. With LD, I would relate to an entire conversation that was riddle with nothing but sarcasm. With Gervais, who wouldn't want to have a beer with someone that finds everything funny? I'd also echo Mac's choice with Colbert as well.

Believe it or not, but I'd also get a beer with Heather Graham and be content just to have a conversation with her.

Billy Crystal.... 'nough said

Opie only drinks Milk!!!!