Frequently, people are attempting to make conversation and they ask me an innocent question that I find deeply awkward.
My second favorite is "Are you close to your family?"
Um... yes? I mean, Dr. S and I rearranged our entire lives so we could live closer to them. We see each other quite often and go on various shopping errands for each other and I've just spent a combined total of about 70 hours knitting my sister an elaborate hat-and-scarf set per her request. And we like each other and maintain reasonably good boundaries. And then there's my middle sister, to whom I almost never speak, who seems to be going through her post-college-discovering-the-world phase, but ten years after college and after two children and a divorce instead. For example, she exhorted Prudence and me to read "Lean In", as if, for one, we'd never heard or read of being assertive, and for another, as if 'play the game harder and surely you'll win like me' were the most useful advice ever.* (For the record, I prefer more constructive works like "Beyond Bias and Barriers", "Lifting a Ton of Feathers", "Women Don't Ask", and "The Price of Motherhood", which at least give concrete advice, such as "Ask for more money.") My spouse says "Yes, you are extraordinarily close to your family."
However, here in the Baptist-heavy South, my very favorite casual, awkward question is "Are you religious?"
This seems so simple, and yet it's so complicated. To a Jew, 'religious Jew' usually means Orthodox or black-hat (Hasidic), although there are plenty of committed, practicing, believing Conservative, Reform, and Reconstructionist Jews in the world. Perhaps what people mean to ask is, do you belong to or go to services at a religious institution? Do you believe in or pray to a deity? Do you participate in religious traditions? How are you working that out with your children, in a place like this? Are you the bacon-eating, Christmas-celebrating variety of Jew, or not? I never know what to say other than "I guess."
* In case you don't want to read the whole article: "Lean In’s goal is to push women forward into their work so as to overcome what Sandberg represents as women’s universal internal resistance to career velocity.... Life is a race, Sandberg is telling us, and the way to win is through the perpetual acceleration of one’s own labor: moving forward, faster. The real antagonist identified by Lean In then is not institutionalized discrimination against women, but women’s reluctance to accept accelerating career demands... By arguing that women should express their feminism by remaining in the workplace at all costs, Sandberg encourages women to maintain a commitment to the workplace without encouraging the workplace to maintain a commitment to them."