Huh, I don't remember seeing Pittsburgh dates back then, though if it was after August I would have been annoyed because I was off in Syracuse being educated. If they plan a Pittsburgh date now, though, I will be around to attend.
As for suggestions....an umbrella and rain shoes (we had a month of Spring in April and it's been cold and rainy since). As for actual city things, I live in a suburb and while I work in the city, I pretty much stick to working, getting home, and Squirrel Hill, the Waterfront (stores and restaurants) and the non-bar side of the South Side (more stores and restaurants and less drunken college kids). I'm of no help with the cool, obscure places in the city...or even the uncool places.