I am 23 and make around $70k. I live in Chicago on a pretty prominent street (when I say my address I get the typical "oooh fancy"), live alone, and I am about to grab a 2nd place in Milwaukee tomorrow (yay!)...

Does money/assets help me or hurt me? I don't have a cocky attitude about money and I definitely don't want a girl who only wants to go out because I'll buy her Woodford Reserve all night, but is subtly flaunting this okay?