I have two suggestions, although I'm not sure they'd entirely fit the bill if you're really trying to "impress" -
Lula Cafe in Logan Square, just up the road from you; the food is good and creative and the crowd is hipster; it's a little small and crowded, though, and I'm not sure what the noise level is like on a Saturday night.
In the other direction, the Flying Saucer on California just south of Divison has (in my opinion) amazing food, same hipster crowd, more room and slightly better decor than Lula. It's also likely to be quieter on a Saturday night, especially the later you go. The neighborhood is not exactly a hot spot for nightlife, but there's the California Clipper just down the block.
or there's the Cuban place (name escapes me, but someone will surely know it) on Armitage just west of Damen . . . loud but fun with nice service and decent drinks . . .
hope this helps; if not, please disregard!