20 Honest First Date Questions I Wish I Could Ask Men

The First Date013B

First dates are painful by nature. It’s essentially an interview where you learn about the other party’s life in general, while getting a glimpse of their personality and ultimately deciding if you two get along enough to see each other again.

However, like interviews, you have to be on your best behavior and sometimes your true colors don’t exactly shine through. That’s reserved for three or four months into the relationship when you throw the clicker at the TV because he passed on watching “Breakfast at Tiffany’s” and run crying from the room.

Since time is our most valuable asset because we only get a finite amount of it, the following are some honest first date questions for chicks to ask bros to truly cut to the chase. Maybe even getting months if not years of your life back in the process that would have been lost to a tedious relationship.

  1. How long do I have to be here for?
  2. Are you going to pay for my drinks?
  3. Do you realize I don’t understand what you do for a living? Everything in terms of finance is diluted down to “he plays with money”.
  4. Are you going to figure out I’m a burgeoning alcoholic if I keep ordering straight vodka?
  5. Do you think I’m A) Amusing B) Have serious issues masked by a blinding need to appear humorous C) All of the above?
  6. Do you like my boobs? My body has to make up for a large part of my personality.
  7. Would you like to eventually meet my family? They’re crazier than I am so you should run now.
  8. How often do you go to the gym? Are you Patrick Bateman? And if not, can you become him?
  9. Where did you go to school because with such little common ground, I will harshly judge you on your answer, as will you.
  10. Can we not talk about your last relationship? I really, really don’t care.
  11. Do you have an intern I can date instead?
  12. Do you have a summer home I can eventually go to to avoid you?
  13. How do you feel about having bastard spawn?
  14. Can you order appetizers? And yes, that is plural.
  15. How do you feel about sweatpants and Netflix? Because the two combined is kind of a hobby.
  16. On a scale of 1-10 how crazy were your past girlfriends? I need to gauge your threshold for it, because I’m an 11.
  17. What sports teams did you play on? Were you a captain in high school? I’m still pissed I didn’t get to sleep with one of the soccer captains so by your having been one I can fulfill an unsatiated, decade-old need.
  18. What is your average text response time?
  19. Is this how you normally dress or is this your go-to first date outfit?
  20. Do you realize I’m utterly insane?


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Writer in NYC. To quote Dr. Seuss, "Being crazy isn't enough."

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