Etiquette and tips for setting up dates

My best friend is 31, single, and is doing well for himself. He is very smart and logical (engineer background), but with an attitude to match. Some would say he's socially somewhat awkward, or immature, or even borderline socially inadequate. That is to say, he says what's logical but not necessarily proper for the situation when he does speak, and the conversation stoppers can be somewhat hard to recover from. To give you a vivid example, think Jack Nicholson in As Good As It Gets. And I have taken it upon myself to find him a good woman. Today I managed to set up a dinner. The dinner party comprised of myself (married), a married couple (friends of mine who are friends with the woman), the woman, and my friend. We went to Dave & Busters to eat dinner and played the games afterwards. D&B turned out to be a poor choice because it was too loud. Not much real conversation. I'll also admit I did a poor job carrying the conversation. Fortunately my friend (wife of the married couple) helped a great deal. I think we can get better at this with practice. It looks like my friend MAY get another shot at her based on the ladies' room conversation and that she said she'll use the D&B (with some credits left) for "next time." Today I didn't get much good words in for my friend, and I plan to do it next time. Could you enlighten me with your experience on this topic? Some of the things I can think of now are 1. the proper etiquette, 2. picking the location and things to do 3. who pays the bill 4. things to lookout for/reminders for someone in my role Any thoughts/experiences on this matter is greatly appreciated. BTW, she's really cool and I like her.