14 Unconventional Questions to Ask on a First Date

I’m a bit of a dating expert. Whoops, sorry, had a typo there. I meant to say that I’m a one-date wonder, who has been on so many first dates that I’ve perfected the art of conversation with strangers.

What’s my strategy? Well, I kind of like to cut to the chase. No wasting time on small talk or appetizers—I need to get down to business. For me, it’s all about asking specific questions, weird questions, trick questions, anything that sparks conversation and maybe a little super-ridiculous debate.

So you might be wondering, Ali, dating guru, what should I be asking if I want to find the love of my life? First of all, I’m more of an anti-dating guru, an expert on what not to do. But, after years of dating, boyfriends, flings, failed relationships, and some great ones, I think I may have fine-tuned some first-date questions down to a science. Here they are.

1. Did you cry when Dobby the House Elf Died?

If you didn’t cry when Dobby died, then you have some serious vulnerability issues. I still can’t watch that scene without sobbing into a bowl of froyo. But that’s just me.

2. Have you ever used the Kelvin filter?

We need to talk about Kelvin. If you find out your date has or is ever planning on using the Kelvin filter on Instagram then RUN FOR THE HILLS HE MIGHT BE A SOCIOPATH WHO WANTS YOU TO LOOK BAD IN PICTURES! Or he might just not know about Kelvin, so you can cut him slack and explain why Kelvin is such a problem. Bad filter! Very bad!

3. Do you use a lot of emojis?

If so, can you spare a moment to teach my mom how to use them? Pretty please? I’ll owe you.

4. Would you ever pumpkin latte shame me?

I refuse to apologize for thinking seasonal beverages are fun!  If you don’t love me at my Pumpkin Spice Latte, then you don’t deserve me at my Oprah Chai, you know?

5. Do you consider bread pudding to be pudding or nah?

Nah. Nah. Please let the answer be nah!

6. How many naps are too many naps?

Trick question. There are never too many naps. My ideal relationship involves a 3pm nap every day. I don’t even care if I’m the big spoon. #BoysNeedCuddlesToo.

7. If you found out 6 months into dating me that I’m not actually allergic to parsley, I just don’t like it, would you break up with me?

Let’s ignore the fact that I’ve been lying to you and more focus on how gross parsley is.

8. Are toes important to you?

Asking for someone who has weird feet. She’s not me. Swear.

9. What are your thoughts on the PT cruiser?

You: It has a revolutionary body structure! It’s so interesting looking!

Me: ….Is this our first fight?

10. How many times do you wear your jeans before washing?

Because I’d like to have a nonjudgmental relationship rule when it comes to laundry, if that’s okay.  Don’t be surprised if I’m wearing my “Wednesday” Day of the Week underwear on a “Sunday.”

11. Would you give me free reign over your Netflix, HBO Go, and Hulu Plus passwords?

Sharing is caring, and mama has a lot of True Blood to watch. PS. Do you care if I call myself mama sometimes?

12. If I was depressed, would you spend the entire day talking in the *Bane Voice* until I felt better?

13. Would you rather back into a parking space or parallel park?

*crosses fingers* please say neither, please say neither, *crosses fingers*

14. How many phone chargers do you have, and do you have an outlet next to your bed?

Now that I think about it, this should probably be question number one….

So, maybe these are some questions you should ask on your first date. Or, maybe throw everything I just told you out the window. What do I know? Be open to something new. Have fun. Practice vulnerability, kindness, and authenticity with a stranger. Who knows what you might find. That’s what dating is all about, right?

(Images , via)