omg you should ask for the full wine tasting then quiz them on the different types. then have two different ones with dinner before ordering and change it up. just be as high maintenance and informed as possible.
and ask for as many grill cheese as you can. but that you want it for an entree. then the entree for desert. with cheese. and a sundae. and then a moscow mule but extra vodka just put a splash of the juice in it. then more cheese. then henney+grand marnier.
that's what i'd do.