First dates are supposed to be sweet, gentle, maybe a little awkward — you know, two humans cautiously poking each other with conversation like “hey… do you have hobbies?”
Personally I think that’s a waste of perfectly good chaos. If I’m taking time out of my life, putting on real clothes and sitting across from someone who may or may not still use Comic Sans unironically… I want answers. Not vibes. Not small talk. Answers.
That’s why I’ve curated a list of my top-tier, highly effective and absolutely not-dangerous-in-any-way first-date questions. They’re bold. They’re revealing. They’re the social equivalent of mixing three different kinds of alcohol and hoping for the best.
But like… if you’re gonna panic someone on date one, you might as well do it with style.
Trauma Breakfast
- If you had to kill someone — who’s first?
- Rate your worst emotional breakdown… in percent.
- How many of your breakups involved police or blocking?
- Do you think you’re the problem?
- Which childhood trauma is currently the most active?
- When your parents call, do you answer out of love or obligation?
Capitalism Meets Nervous Breakdown
- How much money is in your account right now — honestly?
- If I left you, would you demand alimony or revenge?
- Are you more Sugar-Daddy/Mommy or Sugar-Victim?
- What’s your most expensive loneliness purchase?
- If we got married, would you put me on the house deed?
- How often do you consider tax evasion purely on principle?
- Would you say you’re more broke or emotionally insolvent?
Physically… Concerning
- What’s the longest you’ve gone without physical affection?
- What’s the most disturbing thing you tried in bed — voluntarily?
- How do you feel about sex without emotional connection… or without lights?
- Which bodily fluid fascinates you the most?
- If you found me attractive, would you say it or just project onto me?
- When was the last time you thought “worth it,” even though it wasn’t?
Mental Gymnastics (with guaranteed fall)
- Would you rather show your feelings or suppress them stylishly like an adult?
- On a scale from 1 to “my therapist knows my birth chart,” how bad is it?
- If you had to date yourself, how long could you handle it?
- What’s the lie you tell most often to seem more likeable?
- If you’re a red flag — what shade exactly?
- How often do you pretend you’re okay just to gaslight yourself?
Relationship Hell
- Why are you really single?
- How many screenshots from your last relationship do you still have?
- If I got up and left right now, would you stay seated or post about it immediately?
- How fast would you give me your password?
- Do you think love is real, or just a collective psychosis?
- If you ghosted me, how would you justify it?
- How many people have you loved and hated at the same time?
Spiritually Disturbing
- Which demons accompany you the most in daily life?
- Do you think we were toxic to each other in a past life?
- If I guess your zodiac sign, can I judge you?
- Ever flirted with a Ouija board?
- How many ancestors would you disappoint by kissing me?
- If you died today, would your Tinder bio make you proud?
Candlelight Existential Crisis
- Why do you think you deserve happiness?
- If no one ever loved you again — would you still be you?
- How long can you endure small talk before dying inside?
- Do you think objectively good people exist, or just better-packaged narcissists?
- What would your last thought be if I paid the bill right now?
- Do you have favorite ways to fail?
Bonus Questions for Absolute Chaos
- How many people in this room would you lie to just to be liked?
- What would you do if you knew I’d leave you in a year?
- If I cry — sexy or annoying?
- Which lie about you should I believe to keep you interesting?
- If you had to marry me right now — would it be out of love or fear?
- Would you entrust me your trauma or wrap it nicely in humor first?
- How long does it take you to destroy someone you love?
If you actually decide to use any of these on a first date… wow. Iconic choice. But I respect the commitment to the bit.
And now I’m curious. If you ever whip out even one of these questions, please come back and tell me how it went. Did they laugh? Did they panic? Did the waiter start hovering just in case? I want the full post-date debrief — screenshots of the aftermath are also accepted.