Who would it be? I would personally pick Wheatley from Portal 2. While kinda a screw-up, he's frickin hilarious.
Edit: Just to clarify, I meant like an artificial intelligence, a machine.
Edit: Cortana seems to be the favorite here (no surprise).
						
					
					
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	Either Cortana or R2-D2. Although Cayde-6 would be good to have a drink with...
 
										 
					 
		    