Well, to begin with, you could shoot Scraper the moon. If he doesn't like watching Playoff level hockey and football, maybe he'll enjoy looking at your ass instead. If Scraper doesn't like watching Pittsburgh Baseball, well, no one will hold that against him. Even a dominatrix cant stand watching that much pain.
Then, when you pull your drawers up and assuming you have a car, Century Three Mall http://www.simon.com/mall/default.aspx?ID=155
is in your vicinity.
So is the Waterfront. ( http://en.wikipedia.org/wiki/The_Waterfront
Both are good to kill an afternoon or an evening.
Also, you don't want to miss parking the car down at Station Square http://www.stationsquare.com/
ad riding the Incline up Mt. Washington for one of the best views of Downtown. Go in the evening and wait for nightfall and take a good camera if you can.
The South Side is down the road from station square. in fact it is halfway between West Mifflin and Station Square. East Carson Street is the main road, and you will never see more bars on any street in perhaps the whole nation. 3-5 of them to a block. it's where the college crowd from across the river hang out.
Email me if these sorts of thing aren't what you were after. I can suggest museums and other cultural stuff in the area if sober fun is more your concern. Do be sure to find a Primanti's Bros. somewhere, though. Pastrami might me a safer choice for a first timer who is not so sure about greasy and garlic Kolbassi.