If there is one thing that I think is a shame, it's seeing people from an individualistic, artsy fartsy town like Ann Arbor having to show their roots by wearing an "I [heart] New York" rip-off "I [heart] Ann Arbor" t-shirt.
Someone once said, "if something is worth saying, it is worth splattering on a pile of paint layers alleged to be covering an actual rock."
... and that's what we did. So don't be a poser. You are representing a city artistic and absurd enough to allow a pile of paint to sit at a major intersection for generations, your shirt should probably reflect that. If you are an alumnus, this is guaranteed to sniff out other alumni in a big city (field tested at Duffy's in Chicago!)
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