Shelterdog...I'm with Seeker on this one. It can be very liberating to go to a restaurant alone...not necessarily to sit at a table, but try the bar when there's an exciting sporting event on. Order a burger and a beer and just enjoy your time...bartenders are usually chatty and the game itself can provide a good conversation starter with others sitting near you. Or, try a coffee shop...not necessarily one where everyone is tapping away on a laptop, but the old fashioned kind where people meet up to have conversations...just bring a book or a newspaper...be willing to offer up a seat at your table if you see someone looking for a place to sit...they'll be grateful! Since you're in Chicago, try La Colombe on West Randoph Street...they have one in Philadelphia and I've met TONS of people this way...(and I'm 43)...

By the way, the art of conversation can take a bit of work if you don't have it naturally...but, I think the key is just to be open...not open to any crazy wackadoo that wants to talk to you...but to different types of people...