"Dating someone substantially younger won't make you look hip; it will make you look like a pedophile." Dirty old men beware.
But back to Wicker Park. In Lanham's barroom parable, one of the pledge brothers gets charged $6 for a bottle of Budweiser by the wash tassel tending bar; not only is his taste in music ishtar, but he's got the nerve to ask for Buffalo wings. (While it's true that "lately, many hipsters have become devout carnivores who take great pride in a meat-heavy diet," a fondness for kitsch is important, so better to stick with sloppy Joes and meatloaf.) Our handyman Bipster friend, meanwhile, tips heavily on his first bronson (a Red Hook) and gets offered a freebie—which he declines, just as he passes on the sex she offers him later in the night; turns out he "jerked off earlier to 'Girls Gone Wild.' "
Does it matter if he did it ironically? He didn't get laid, and he didn't even pay less for his beer. No wonder the squares never learn. As Tower of Power also sang, "Sometimes hipness is what it ain't."