I'm a longtime lurker/infrequent poster on LTHFourm but thought I'd share my experience last night at an event arranged by grubwithus - a new Chicago site in private beta (
http://grubwith.us) that markets itself as an "experiment in social dining." The idea is you basically reserve a "seat" at a table at a restaurant and then show up at a certain time and share a meal with strangers who have also reserved seats. I was one of 10 last night.
In short, I had a great time and think the concept definitely has lots of potential - especially among people new to Chicago or people traveling in Chicago who don't have anyone to eat with. Also, since you pay for the set-price meal before you show up at your reservation (I paid $15 for a multi-course, family style meal with no tip included) it removes one of the worst hassles of group dining: settling the final bill. If you order drinks the restaurant creates a separate tab drink for each person.
And now I'm sure you're wondering, "How bad was the 'awkward silence' factor"? I wouldn't say it was an issue and after the first courses came out everyone was very chatty. My only complaint is that it was difficult/impossible to have a conversation with people on the ends of the table but that's just a reality of group dining.
Not sure if any other LTH'ers have been to an event yet but I'd personally love to see some GNRs as future locations for grubwithus events. To the best of my knowledge they've done Thalia Spice, Cafe Bolero and (soon?) Sappori Trattoria.
Full disclosure: I'm not affiliated with grubwithus in any way, except to say I met both the founders (also the owners of Beard Papa's) at the dinner last night and thought they were cool guys who have a good idea.