20 Things I Wish I Could Ask on a First Date

I wish I could ask a lot of questions on first dates, rather than finding this information out later and when it’s far too late.  There are simply too many guessing games when you begin dating, and being able to interrogate each other would really help.  Perhaps online dating is better in the sense that you know certain things ahead of time…  That said, here are the 20 questions I most wish I could ask on first dates and get truthful answers:
  1. Do you live with your parents?  If yes, why?   If this person is over 24, they better have a real damn good reason for living with mama and papa.
  2. How many people have you slept with?  Were you careful or careless?  You gotta avoid the dirty ones.  Plus, the bigger the number, the lower the standards.  Why so many?  Why so few?  This question teaches you so much.
  3. Do you have any STDs/STIs?  DEAL BREAKER
  4. Are you pro-gay rights? And, does anything about the LGBT community make you uncomfortable?   I could not be more pro-gay.  I need someone who is comfortable with and supportive of all things LGBT.
  5. How much time do you actually spend playing video games/watching sports/”Intervention”/”Entourage”/some other obsession?  Know thy enemy.  In this case, you just want to know what you are competing with for their time.  If they regularly stay up all night to watch this or play that, you should get to know now.
  6. Are you an asshole/douchebag/shithead/dick/jerkface?  DEAL BREAKER
  7. Are you afraid of the outdoors, the country, nature and all things rural?  I’m a country girl.  I like camping.  I like hiking in the woods.  I like trees and hills and lakes and rivers.  City slickers beware.
  8. What’s really more important: sex or love?  Compare priorities prior.
  9. Do you enjoy dancing foolishly, or do you feel foolish dancing?  I am not afraid of looking like a weirdo, are you?
  10. Do you fight fair?  Ladies and gentlemen shouldn’t be dating people who go crazy by saying and doing awful things to their partners when they fight.  It is not cool to call each other hurtful names, to throw low-blows, to hit (whether wall or person), to break things, to intimidate, and to lie.  Settle down.  Everyone bickers.
  11. Do you love, hate, mock, or feel ashamed about “Buffy The Vampire Slayer,” “Harry Potter,” “MST3K,” “Angel,” and other amazing, nerdy things?  Again, I am a nerd.  Deal with it.
  12. Would you kill a spider for me?  How scared are you?
  13. Do you make enough money to pay for dinner half the time?  If not, you need a new job.  I’m not looking for a rich person, but I do want to be able to expect that you’ll pay for at least half of our dates.  I’ll pay the other half, obviously.
  14. How often do you read books – not magazines, papers, or blogs?  I read a little of all, but a lot of the book things.  Compatibility is important, y’all.
  15. How often do you brush your teeth and floss?  My chompers are important, and so is your breath.
  16. Is your mom a bitch?   I ask this because it scares me when people think this about their mamas; unless of course, their mom is just especially awful, then they have a point.
  17. Do you have any children?  DEAL BREAKER
  18. Who is god to you?  I gotta watch out for the crazies!
  19. What are the main differences between men and women?  Watch out for sexist answers!
  20. How big is it?  …  No, not that; I meant your ego.

2 thoughts on “20 Things I Wish I Could Ask on a First Date

  1. I LOOVVVEEE this list! And while my list might not include being a reader (go figure) or being up all night watching tv (my guilty pleasure is Adult Swim) I would have to add…

    Are you a Red Sox, Pats, Celts, Bruins fan?

    Do you drive anything other than an American car? (I will bend my rules for guys who have long commutes and are into fuel economy).

    Believe it or not, the whole “asshole/douchebag/shithead/dick/jerkface” isn’t necessarily a deal breaker for me, as long as it’s contained to cockiness among guy friends. I’ve got a soft spot in my heart for smart asses.

    If I wanted love I’d get a dog so yeah, “sex” trumps “love” any day.

    Again, cool post.

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