Local sights:
Museums: Eiteljorg, IMA, State Museum, Indiana Historical Society, Children's.
Funky bar…coming into my Old Curmudgeonship early, I have to ask what you mean by 'funky'? There's all sorts of bars, from high-cover 'place to be seen' to 'small town tavern'.
For food in general, I'd suggest Squealers (BBQ), Yats (cajun), 96th Street Steakburger, Broad Ripple Brewpub, The Aristocrat (lots of Irish/traditional folk music, very good food).
Gaming stores are…well, a lot like gaming stores anywhere else, really. The one really unique (for good or ill) one, Boardroom Games, closed a few years ago (again, for good or ill…) There's Saltire Games, out off of Pendleton Pike: great if you like RPGs, Hordes/Warmachine. They've got open gaming most nights, check their website, call and talk to Phil, he'll let you know what to expect when.
Games 2D4 on the exact opposite side of town – it's the place for FoW. Good selection, lots of tables, Jerry the owner is a great guy.
Best theater: Any IMAX is pretty good. Unfortunately, the Tibbs Drive-In doesn't open until the end of March. Greenbriar Cinema Grill is reasonably priced, and you watch the movies from dinner tables. Food is okay, movies are second run, but often good. Keystone Art Theater shows movies that don't get play anywhere else in Indy.
If you want to stay downtown, The Ram is an excellent restaurant/bar. Not so much on the funky side, unless you come during GenCon. :) About any downtown restaurant is good – they're all in fierce competition for local and convention dollars, so you're pretty well off choosing whatever you like.
Last of all, ask the locals! 'Hoosier Hospitality' isn't just a catch-phrase, and you'll probably discover something awesome that I've completely overlooked.
