This is an intriguing list request that I somehow overlooked from three months ago. Thanks, @tombatten!
  1. "Do people that work here tend to leave in a damaged, traumatized state that takes years of professional help to recover from?"
    When I accepted a job offer to write pornography for a living at age 22
  2. "Exactly how long has this tray of shrimp been sitting out at your New Years party, and at what level of refrigeration?"
    New Years Eve, 2000, which - as I heard people counting down from inside the house - I was in the bushes, vomiting through my nose
  3. "Has anyone taking these shrooms experienced side effects such as seeing a UFO, then lying face down in the desert, crying and attempting to telepathically contact an ex-girlfriend?"
    New Years Eve, 1999
  4. "Has anyone, ever, in the history of the world, had a positive experience as the result of doing cocaine?"
    Las Vegas and Sacramento, 1998
  5. "Do you have an extremely troubled personal history that you've taken no steps to deal with whatsoever?"
    Every romantic relationship I got involved with before the age of 30
  6. "So after using these 'credit cards,' do you expect me to actually pay the money back?"
    1994 - 1999
  7. "Is this movie any good?"
    On my way in to see "Noah" starring Russell Crowe