7 Can't Miss First Date Questions


first date conversation
First date conversations can be rough; here are some softballs.

I'm not sure that there is any actual data to support this, but first dates can provide some of the most stressful moments in a person's life. It doesn't matter if you like your date or not; it's just crucial that they like you.

Unless you're one of those types with unhealthily high levels of self-esteem, self-awareness and self-love, you have probably felt a crushing amount of anxiety at the prospect that someone wouldn't immediately think you're the cat's PJs. The good news is that you've already made enough of a first impression. After all, this person agreed to a date with you (unless it's one of those blind dates, in which case it's an absolute crapshoot, even with the best of preparations). But what do you do now?


Some people say that certain topics are off-limits for first dates, and there is some merit in that assertion. Which leaves small talk as your primary option for interaction. But while you may think that small talk is just a bunch of petty chit-chat, it need not be a mere exercise in abject banality. You can learn a decent deal about someone using largely innocuous questions, and decide later on whether or not you're up for sharing more important stuff. Plus, this initial conversation could give you some great hints at future gift ideas. Don't be a jerk about it; slide these in there real casual-like. And, like any good investigatory journalist remember to infer "why." Read: First Date Conversation Topics

  1. "If you were to be trapped in an elevator, who would you like to be with? Present company excluded, of course."
  2. "Do you have siblings? If so, how many, and in what order were you born?"
  3. "Have you ever been to [insert your favorite travel destination that's not synonymous with prostitution or drugs]?"
  4. "What's your favorite word?"
  5. "What skill [or super power, if you're frisky] that you do not possess would you most like to have?"
  6. "What's your favorite thing about yourself, non-physically*?"
  7. "Would you like another drink?" Read: 4 First-Date Conversation Killers

Under no circumstances should you ask if you sat in some gum, and then expose yourself.

As always, holler with more questions.

*Note: If I had a nickel for every time I heard "breasts," I would have more money than I do now.


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