40 Questions To Ask Them Now.

Aka: possibly just autistic flirting.

I have a habit, one that some might call charming, and others might call borderline interrogational, of asking the people I date deeply personal, oddly specific, and sometimes outright invasive questions. Not in a malicious way, of course. I just find that the typical small talk of early dating often feels tedious, like a rehearsed script we’re all performing. Instead of the usual "Where did you grow up?" or "What do you do for work?" I prefer to dive headfirst into the weird, intimate, and existential.  

This approach has its perks. It skips the surface-level pleasantries and gets straight to the heart of who someone really is: their quirks, their anxieties, their secret soft spots. And honestly, I just find it more fun. What’s the point of dating if not to peel back layers of another person’s mind and see what’s inside?  

Over time, I’ve compiled a list of my favorite questions to ask: the ones that spark the most interesting conversations, reveal the most unexpected truths, or simply make people laugh. Some are lighthearted, some are introspective, and a few might make your date pause and say, “Why would you even ask me that?” (Which, to me, is the highest compliment.)  

So, whether you're looking to spice up a first date, deepen an existing relationship, or just make someone squirm in a delightful way, here they are, from my notes app to you:

What oddly specific thing do you find attractive?

What’s the best compliment you’ve ever received?

What do you have great taste in?

What do you think all the people you’ve dated have in common?

Is there anybody you wish you never dated?

If you had one wish granted, but it had to be for someone else, what would you wish for?

Is there a moment you wish you could relive (not to change it, but to experience it again)?

What part of yourself are you currently working on the most?

What’s one thing people always get wrong about you?

Have you ever resented anybody?

What’s one thing you wish you could change about yourself?

What was your bedroom like as a child?

What’s the last stupid thing you did?

How do you think your friends would describe you?

What’s the worst physical pain you’ve ever felt?

How do you typically masturbate?

What quality do you find really annoying in a person?

Are there any foods you eat every single day?

How would you describe the way you apologize? How would you like to be apologized to?

If someone got you a cake for your birthday, what kind of cake would you want?

What’s your favorite kind of cookie?

How would you describe your sex drive?

What are your thoughts on giving money to people without housing?

Do you have any thoughts about Stephen King?

What’s the last song you listened to?

What kind of croissant is the best croissant?

Is there anything you struggle with sexually—mentally, physically, or emotionally?

At this moment, who do you think knows you best?

Do you have any scars?

If you had to kill someone right now, who would it be?

Do you like peanut butter? If so, what kind?

Have you ever played any kind of organized sport?

How do you pick what clothes to buy?

Are you scared of the ocean?

Do you have any recurring anxiety dreams?

If you could pick your own name, what would you change it to?

What is the worst job you could imagine having?

Did you ever write poetry when you were a teenager?

Can you tell me a dad joke off the top of your head?

How would you describe your relationship with your ego?

At the end of the day, dating is just getting to know someone well enough to decide whether you want to keep knowing them. And while deep, meaningful conversations don’t guarantee compatibility, they do make the process a hell of a lot more interesting.

Maybe these questions will help you uncover something unexpected about a new partner, or maybe they’ll just spark a weird and hilarious debate about the superior croissant. Either way, asking better questions leads to better conversations, and better conversations lead to real connections: the kind that make dating feel less like a chore and more like an adventure.

So go forth, interrogate with charm, and have fun judging their answers.