man and woman sitting with coffee on a first date

The Best First Date Questions That Will Charm and Amuse!

We always, no matter what, want to make a great first impression on a first date and want to feel like we’ve made a connection. However, there inevitably comes a point in the conversation where it just kind of dies, and no one knows what to say! That said, it’s always important to have an engaging question, no matter where the conversion is! One of the best ways to accomplish this is by asking great questions that spark intriguing discussions! 

Oddball Questions

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One Redditor shared, “What unresolved childhood trauma will emerge through maladaptive behaviors as we spend more time together?”

To which a second Redditor added, “Your parents are about to be executed. You are given a chance to save only one of them. Which one do you choose?”

Funny & Anecdotal Questions

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A Redditor supplied, “What’s the largest mammal you think you could knock out with a single punch?”

This user offered, “Ask them who their favorite muppet is.”

A user also said, “Favorite dinosaur?”

Food & Dining 

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A top-liked comment said, “What’s your worst cooking disaster?”

A Redditor hilariously added, “Which vegetable offends you the most?”

A user kept it simple and said, “What is your favorite type of cuisine or food?”

About Pets

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This user shared, “What was/is your first pet’s name?

While a second user asked, “Did you have pets growing up”

Travel Experiences & Destinations

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A Redditor had this to say, “What was your favorite trip/vacation, and why?”

A Redditor left this comment, “What is your dream travel destination of yours?”

Ice Breakers

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A user added, “What was your second-grade teacher’s name?”

This user said, “What was the make and model of your first car?”

Personal Interests & Hobbies

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A Redditor stated, “What are your favorite hobbies and activities to do in your free time?”

A second Redditor said, “What’s one hobby or activity you’ve never tried but always wanted to?”

Relationships & Dating

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One user shared, “What are some relationship red flags or deal breakers for you?”

A second user said, “What’s the worst pick-up line you’ve ever heard?”


Validate Feelings: woman sitting and smiling with a coffee cup
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A user commented, “What do you think is the most fascinating thing about technology?”

While this user replied, “What is your favorite piece of technology you own?”

Education & Academic Pursuits

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This Redditor added, “Did you go to college? If so, what did you study?”

Another Redditor said, “What made you choose the college/university you went to?”

Dreams & Aspirations

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A user stated, “What are some dreams and goals you have for your future?”

Another user commented, “If money wasn’t an issue, what you be doing instead of what you’re doing now?”

Favorite Books, Movies, & T.V. Shows

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A top-liked comment said, “What’s on your must watch/read list?”

This Redditor shared, “What did you watch or read because of a recommendation that completely blew you away?”

Childhood Memories

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One Redditor added, “Do you have any funny or embarrassing stories from your past?”

While a second said, “What is the name of the road you grew up on?”

Sports & Social Events

Women on Bicycles two women riding bikes at the beach
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This Redditor shared, “Most memorable concert or live performance you’ve attended?”

A Redditor asked, “If you could go back in time to any concert or sporting event, what would it be and why?”


Happy couple hugging and laughing
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A user said, “If you had to choose a new name, what characters, numerical, uppercase, lowercase, and special included, what would you choose?”

One user said, “If you had an hour during which any crime was legal and socially acceptable, what would you do?”

Fun Facts

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This user commented, “What’s your favorite random fact?”

A user asked, “Do you put your toilet paper on the holder with the loose end over or under?” 


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A user added, “What’s the most spontaneous thing you’ve ever done?” 

Essential Items

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One Redditor commented, “What would be the hardest thing for you to live without?”

This Redditor inquired, “What’s one thing you never leave home without?”


Open-mindedness man showing a thoughtful face
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This user asked, “What would be their weapon of choice in the apocalypse?”

A user shared, “If you could only bring a shoe box full of items to survive on an island for one year, what would you bring?”

Legal Matters/Criminal History

Man in handcuffs behind his back
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This Redditor said, “Do you have any outstanding warrants?”

Finally, a Redditor said, “Have you ever been in handcuffs?”

So there you have! We’ve delved into the realm of first date questions, seeking the perfect blend of curiosity and connection. From childhood dreams to secret talents, these inquiries serve as gateways to understanding and discovery. Remember, though, that no list can replace the spontaneity and genuine flow of conversation. So go forth, armed with these suggestions, and let the sparks fly on your next romantic rendezvous. And who knows, maybe one day, you’ll be sharing your own memorable first date experiences with Redditors. Happy dating!

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