It's also worth noting that different people have different ideas about what constitutes an awkward silence. It may be that the reader starts feeling awkward a few seconds before her conversation partner does, so she's always the first to start talking again. I'd recommend slowly counting to 10 during a pause to see if her date will start talking before she does. (D.A.R.E.'s also got some good suggestions for open-ended questions.)
I can't stand "would you rather" questions where both options are really horrible (i.e., I can rank the states I'd like to live in, but I can't pick a limb I'd rather to lose), so I guess that makes me "devoid of feeling, humor, or opinions."
