I live way up on the North Side, but the fellow I'm seeing lives in the West Loop, and I didn't realize until last Saturday night how very close he lives to Taylor St. (we went to Hawkeye's to watch the Red Sox and have some chili and a couple of beers, and it took maybe five minutes to get there from his house). Oddly, even though he loves good Italian food, he's never really explored it at all, and it seems that it's high time he did (and by proxy, me, too).
What should we try first? And second? And third? He's a low-key person who's not much for dressing up - and neither am I, truth be told. Please share what you like best, so that I can share with him.