Writer Response: 31 Questions For You To Ask Your Next Date

By Sunday Scaries

I normally head to Thought Catalog to read needy post-grads girls justify why it's okay for them to be single, poor, and awkward. But not today. Today, rather than someone writing something called "87 Reasons It's His Fault Your Relationship Deteriorated" or "39 Ways To Lie To Your Friends About Staying In Because You Hate Them," Thought Catalog published an innocent piece titled, "31 Genuinely Interesting Questions For You To Ask Your Next Date."

We all know crush first dates, so naturally I had to take this one for a spin. 

As always, original article in italics.


I have a complaint and I am so ready for the internet hate I’m going to get for it. BRING IT ON. As an extrovert I am really good at starting conversations and keeping them going. That being said, I’m really tired of going on dates and not feeling like there’s no give and take. I’m tired of asking all the fun questions! And I’m so sick of the standard “date” questions. It’s really, REALLY attractive when people ask well thought out questions that at least give the illusion that they want to know me better. And I mean REALLY know me. Not just know where I went to college and what my worst OkCupid story is. Good questions are sexy. Hint hint, nudge nudge, fellas. 

You use OkCupid? Isn't that for poors?

So here ya go. 30 questions you can bust out on your next date that will make the person sucking their last bit of their vodka soda stop and say, “Wow, what a great question.” My gift to you.

Alright, Kendra, let's do this.

1. Who inspires you? Who do you aspire to be like?

My current style inspiration is Chandler from Friends. For example, I'm literally wearing this right now. It's an XL cotton Vineyard Vines sweater that I gave to my dad for Father's Day a few years back that he accidentally shrunk in the wash. So while the length of the sweater errs to the medium side, the arms and body of the sweater are actually abnormally baggy which gives off a super 1999-2001 vibe.

Considering that in 2013 I called that turtlenecks would be popular as fuck (see: every Man Repeller post this winter), you might as well stock up on oversized v-neck sweaters because everyone's going to be dressing like their on the set of Mad About You come December 2015.

2. What was the last book you read without skipping through anything?

The last book I read straight through in one sitting: A Drive Into The Gap, because I get off on baseball and nostalgia.

The last book I just read: 41: A Portrait of My Father because I get off on the Bush family and nostalgia.

3. What is the weirdest scar you have and how did you get it?

I got run over by a car, Kendra. Read my fucking website just one time for me, please. 

4. What is the most random thing you’ve ever watched all the way through on Netflix?

If I'm being honest, I was high one time and watched like ten straight episodes of Arthur

5. If you could trade lives with one person for an entire day who would it be and why?

Kanye West, and before you jump all over me with "OH MY GOD, HE'S SO POMPOUS, WHY WOULD YOU EVER WANT TO BE HIM?", just hear me out.

Recently, I had to explain to Douchebag Pete why Kanye West is the ideal celebrity despite the general public hating him. The long and short of it: he's controversial, he's cocky, he's smart enough to be self-aware but dumb enough to act like an idiot. Plus, he's actually talented so his fame and fortune are completely justified.

A huge benefit of trading places with Kanye is that I'd finally get to see what wearing leather pants feels like without having people looking at me like, "Is he... or....?" And the kicker? I'd get to chill with Scott Disick for the day while Kim and Kourtney text on the couch.

6. Do you believe in ghosts?

The only "Ghost" I believe in is a song by Ella Henderson. BANGER.

7. Shark diving, bungee jumping, or sky diving?

Shark diving and it's not even close. If you're bungee jumping or sky diving and something goes wrong, you're the fucking idiot who died from jumping out of something you had no business jumping out of. If you're shark diving and something goes wrong, then you're badass who died fighting a goddamn shark.

8. Which would be harder for you to give up: coffee or alcohol?

That's rich, Kendra. Love a girl with a sense of humor. That's a real knee-slapper, there. Next.

9. How did you meet your best friend?

We met before we could form cognitive memories, because that's what best friends do, Kendra. I met another best friend at daycare. He wore Adidas, I wore Nikes, so we naturally hated each other. Our parents made us hang out and play with Legos. Now we text about babes and Snapchat each other while we poop. We live in a disgusting world.

10. Do you have a sweet tooth or a savory tooth?

A moment at the lips, forever at the hips. #BenderThroughDecember and #BulkThroughJanuary took their toll on me so I'm pleading the fifth on this one. Whiskey-Salad Diet until further notice.

11. What is something you’ve always wanted to try but have been too scared to?

Going commando. The upsides just don't seem to outweigh the downsides. When I was going through puberty, I was playing backyard basketball with my aforementioned best friend and I got swamp ass. He proceeded to refer to me as "Swamp Thang" for a good two years after and I've been scarred ever since.

12. What accomplishments are you most proud of?

CLASS FLIRT '05.

13. If you were going to go to the movies alone, what would be the perfect film for you to watch by yourself?

I mean, I have been to the movies alone, and it was Dawn of the Dead. Not super proud of that one, Kendra.

My perfect film to watch by myself is You've Got Mail though. Everyone knows that and you'll realize why as our relationship materializes.

14. What is your favorite Wikipedia article? (Shuddup. Everyone has one.)

Bob Marley's because it taught me that his dad is white. Seriously, did ANYONE know that Bob Marley is half-white? Boggles my mind.

15. What is your favorite physical attribute about yourself?

I mean, the hair. It's always the hair.

This is actually a sneaky phenomenal icebreaker with the opposite sex. It gives them an opportunity to brag, and it gives you an opportunity to compliment. Used this in a Car Bar situation en route to a bar last summer and I'm pretty sure everyone rounded 2nd base that night.

16. Tell me about the best vacation you’ve ever taken.

I went to St. John in 2004 with my family and some close family friends. When everyone left me to go on a day trip (still have zero clue why no one woke me up), I was chilling naked by our pool and got startled by a rogue iguana. The iguana kept creeping closer to the point where he had me pinned (still naked) in a corner of our vacation house for a solid 30-40 minutes. I was deathly afraid everyone was going to come home and find me cowering at the hands of this iguana, but I valiantly escaped.

I've never told anyone that so I'm super excited to get an email later reading, "Dude, did that really happen when we were in St. John?" from my friend.

17. Where is your favorite place to go on a weekday afternoon when you have no plans or obligations?

The gym, because I'm always trying to make gains.

Just kidding, working out is for dweebs. It's probably the golf course because time doesn't exist there which means I can drink whenever I want without judgement. Allows me to come in HOT for happy hour when everyone's off work.

18. What is one of the weirdest things you used to do as a teenager?

In high school, I dated a girl who told me, "You like FIFA more than you like me," and I didn't even deny it when she said it because it was 100% true. I just played way too much FIFA. My kids will never even get close to having a video game system because gaming is the worst. You don't get awesome at flop shots and football by sitting on your ass all day.

19. Gin, vodka, or tequila?

That's like asking "Kim, Kourtney, or Khloe?" I'll take any of 'em if I'm thirsty enough.

20. What drives you to do what you do? What motivates you?

The Rock's Instagram Account. #BootsToAsses #AMCardio #BringIt

21. In your opinion, what is the best Disney movie to come out since Disney’s Golden Age?

Thanks for the Twitter clarification on this one, Kendra. After much deliberation, I'm going with Brave. I've got a thing for accents and redheads, and the whole bear plot really came out of left field and threw me for a loop.

22. What kind of phone was your first cell phone?

Nokia 3310. It was similar to the Nokia brick phone that everyone had, but one step above so it showed all the honeys, "Hey, my parents aren't afraid to spend a little extra on me." Did the smaller keyboard make it a little harder to play Snake? Yeah, but I still held/hold the record in my group of friends because the cream rises to the top, baby.

23. What did you love most about the place you grew up? What about it did you love the least?

There was something in the water in my hometown that gave all of my friends and I incredible flow, and there was something in the water that caused all the dudes from our rival high school to have thin, wispy hair. So yeah, you could say that's what I love most about where I grew up.

And what did I love the least? That question doesn't really make sense but I'm going to go with our lack of an elite high school football program. But that kind of leaves the door open for me to be the next Coach Taylor so I'm alright with that.

24. What trajectory are you hoping to push yourself onto? Where do you want to head?

I've actually been working on my traj a lot lately. I'm thinking about changing from a 3-wood to a high-lofted driver in order to keep my ball flight high while maintaining an optimal angle of descent to gain some distance. Douchebag Pete taught me that.

25. What is your most bizarre talent?

I'm unbelievable at standing on my head. If you play your cards right, I'll show you my yoga journey's Instagram account.

26. Is there a documentary or book that really changed the way you thought about something?

Yeah, Blackfish about the treatment of Killer Whales really opened my eyes. It made me realize that I really fucking need to go to SeaWorld one last time before they shut it down because of all these truthers behind Blackfish.

27. What are three albums (soundtracks or compilations don’t count) that really define you or have shaped you as a person?

Okay, you must follow me on Twitter or something because you knew I was going to answer with the My Girl soundtrack, which everyone knows I enjoy to completion before every date I go on.

But on a serious note, I'd probably have to go with Kid Rock's entire discography, including Live Trucker for when I'm really trying to turn the party out.

28. Who was someone you really looked up to when you were little — someone you considered to be a mentor?

Gordon Bombay from the original Mighty Ducks when he was still in the DUI Diversion Program. He was still enough of a wildcard to do his whole "Quack, Quack, Quack, Mr. Ducksworth" bit, but stable enough to lead the team to the District 5 title.

29. What’s your favorite cheesy pick-up line? Have you ever used it for real?

"Suck me, beautiful" is always a good go-to, but if I'm actually trying to slay then you have to go with, "Is it too soon to say 'I love you'?" And no, it's not creepy to say. You use it as an ice breaker after lobbing the potential biscuit an easy question. Tube Socks taught me that one back in '08. 

30. Who is a character from a TV show or a book that you’ve always resonated with?

Schmidt, New Girl. I think I was Jewish in a past life.

31. Can I get you another drink?

Sure — gin, vodka, or tequila?