18 entertaining questions to ask on a first date to spice things up

Audra Wallkill
Audra Wallkill, here. Your new bitchy sensei. I believe that everyone’s got a freak flag that needs to be flown. If yours is collecting dust in the basement next to your dead dog’s ashes, I’m here to help you get that shit back at full mast. Born and raised in the magical diaper that is New York City, I all but have the dehydrated urine of a homeless man coursing through my veins. My tear ducts have been hermetically sealed (if your mascara is running — how are you supposed to fight the patriarchy?). Truth-serum is my life source, and there is much yet to be uncovered. As I continue the journey, I look forward to sharing my learnings with you. Shine bright like a diamond.


Sweating like a Bolivian drug lord going through customs well into the autumnal month of October may have diluted any sense of urgency, but the fact remains: “Cuffing Season” is approaching. It’s time to invest in a good hair serum and fire up those dating apps for your best chance at locking down a winter spoon.

I know better than most that screening romantic prospects is not for the faint of heart. After a balding divorcee with a pet rabbit duped me with a profile advertising a gorgeous Latino man with a bourgeoning career in finance, I HAD to take back some control.

So, I set out to create a fail-proof list of first date questions to eliminate the bad seeds as quickly as possible. I spent my summer swiping my index finger to the bone, sampling nearly every dimly lit tapas bar in New York City. The questions below are proven to reveal important truths about your date AND keep things interesting in the process. How are they proven you ask? I am currently sleeping with an emotionally stable man with no trace of a criminal record. And, if I can achieve success, there is nothing stopping you, baby…


1. What do you consider your most flawed physical attribute?

At this point you’ve already clocked his short torso or gross feet, etc. This is more a test of self-awareness.


2. What do you consider your most flawed personality trait?

Be wary of people who identify a strength as a weakness. E.g. “I’m a perfectionist” (eyeroll)

3. When was the last time you spoke to your mother?

We want to fall somewhere in the middle on a spectrum between “im texting her right now!” and “she’s dead to me.”


4. Fuck marry kill: Kim, Rob, Caitlyn

Propose marriage immediately if your date does not know who these individuals are.


5. Would you rather get into a horrific accident that leaves you with a deformed face at 45 or die at 45?

Throw this zinger out into the ether when conversation starts becoming pedestrian. Works like a charm.


6. When was the last time you washed your sheets?

In anticipation of a lie, pay close attention to uncomfortable body language, shifty eye contact and abrupt vocal inflection.


7. What’s the most fucked up movie you’ve ever seen that, on the low, you actually enjoyed?

If he says Schindler’s List…get the check.


8. Would you rather eat a baby and no one ever finds out you ate a baby OR actually not eat a baby but everyone THINKS you ate a baby?

If he answers “eat a baby” I’m sorry to be the bearer of bad news but he’s a sociopath.


9. Do you exfoliate?

I personally can’t deal with blackheads.


10. Is that a birthmark or melanoma?

This is just a nice way to show that you care about his health and wellness.


11. La Croix or Canada Dry?

If he says Canada Dry, he’s probably lied to you about his age.


12. Innie or outie?

Wouldn’t you rather find out early on that he has an outie?


13. Please spell the word “foyer” phonetically.

Don’t ever fuck with someone who says foy-yay.


14. What are your thoughts on the hit sitcom “Big Bang Theory”?

If he got excited, he will likely respond positively to the next question…


15. Have you ever owned, purchased, worn, (or thought about owning, purchasing or wearing) a pair of TOM’s and/or Crocs?

I can’t stand that I have to explain this but, a hard no is clearly the only acceptable response here.


16. Are you down to get a tattoo of my choosing tonight?

When you’ve indicated that you’re with a wild card and want to test the boundaries for the fuck of it.


17. Would you like to purchase me a dog?

When you’ve pre-maturely fallen in love.


18. Are you going to eat that?

Don’t you dare leave any tapas on that table. There are millions of starving people in this world.


Choose your favorites and test them in the field for yourself. Report back with success and/or horror stories to [email protected] I’ll be researching top rated but cost-effective body pillows as an emergency backup resolution in the meantime. (You won’t need it.)

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