Questions To Ask On A First Date That Aren’t “What Was Your College Major?”

The point of a first date is to get to know someone, obviously. Even if a first date is going well, they’re awkward and it can be hard to know what to ask someone that’s a complete stranger.

You don't want to only ask the basic questions like "how many siblings do you have?" but you also don't want to ask them to describe they're dark childhood trauma, so what can you ask?

Who Is The Most Interesting Person You've Ever Met?

talking about murder on a first date
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Photo Credit: Twitter / @maggyvaneijk

This one has so many different possibilities, but you’ll be able to learn more about what qualities they value in other people based on what their answer is. What exactly makes a person “interesting” to them?

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What's Your Favorite Piece Of Furniture In Your Home?

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what do you like to do for fun
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This is one of those questions that you might not learn a lot about the person from them telling you that some chair they found at a local market is their favorite, but it’ll get the conversation rolling for sure.

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What Did You Think You Were Going To Be When You Grew Up?

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whats your moon sign on a first date
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Rather than simply asking someone what they do for a living, you can ask them about what they thought they were going to be when they grew up. Chances are no one grew up dreaming of being a financial analyst, but there might be a great back story about why they wanted to be a plumber as a child.

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What's Your Biggest Pet Peeve?

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Pet peeves are something you can easily bond with a person over on a first date. Do you both hate people who are slow walkers or people who text during movies?

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What's Your Biggest Insecurity?

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horse video on a first date
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This is a question that will probably catch them off guard, and even if they don’t end up fully answering it, chances are it will get them talking about some childhood trauma like the time they cut their own hair after they got gum stuck in it.

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If There Were Medals For Everyday Activities, What Activity Would You Win Gold In?

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Maybe you'll learn that he's an expert food prepper and loves to cook on Sundays for the week ahead, or he has somehow mastered the ability to fold a fitted sheet properly (we're not convinced that's even possible though.)

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What Would You Want Your Superpower To Be?

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This one seems silly, but it also tells a lot about someone if they really think about it and consider all the options. Does he want the ability to fly because he loves to travel, or is he trying to escape his ex-girlfriend and all of his problems?

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How Would Your Best Friend Describe You?

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Now's the time where they can shamelessly hype themselves up by pretending that their best friend would describe them as "giving" "selfless" or "incredibly funny" when in actuality their best friend would probably not be that kind.

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What's The Most Memorable Gift You've Received?

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hair dye gift on a first date
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It might be some absolutely awful gift they got for their 9th birthday that still haunts them to this day or it could be that time they got to go to Disney World for Christmas when they were 12.

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What's Your Go-To Karaoke Song?

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Maybe they’ve never done karaoke, or maybe you find out that they absolutely despise karaoke and you know that you shouldn’t suggest you check out that new bar that has karaoke on Thursday nights as your second date!

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What's Something You Were Obsessed With As A Child?

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horse girl concept on first date
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Did they have a doll that they dragged around behind them to every family function until it mysteriously was "lost" one day, or maybe they had a firetruck toy that no one else was allowed to touch? The conspiracy that their parents intentionally threw out their favorite toy will get them chatting for sure.

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What's Something You Can Always Justify Spending Money On?

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Do they always have to have the latest iPhone even if they just bought a new one 6 months ago, or do they love to give their friends and family gifts (even if its not always in the budget?) It's good to know if you have similar spending habits or if they'd put themselves in debt to buy Airpods.

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What App Do You Use Most On Your Phone?

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Are they the normal twenty-something who spends a fair bit of their scrolling through dog photos on Instagram, or are they going to pretend that Apple Stocks is their most used app?

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Would You Rather Be Famous Or Wealthy?

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With questions like this one, you can read into it if you want or you can take it as something silly, depending on how serious they take it. They could be the next Jeff Bezos, or they could be the next Jake Paul. Which would you rather?

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What's Been Your Best Age So Far?

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worst first date ever well cheers
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If he says 17 or starts talking about how much he loved his high school football days, run away immediately before he tries to give you his letterman jacket and convinces you to come to one of his old high school's games next weekend.

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What's The Worst Ice Cream Flavor?

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While it may not seem like there's a right or wrong answer to some of these questions, there absolutely is a right answer to this question. The correct answer is that bubblegum is the worst flavor. The flavor works with gum, not with dairy.

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What's A Tradition Your Family Has?

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He may not be your future husband, but if he does happen to be, it's nice to know what kind of odd family traditions you're going to be getting involved in at Christmas. Do you need to stock up on your ugly Christmas sweaters or up your baking skills?

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If You Could Only Eat One Meal For The Rest Of Your Life, What Would It Be?

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You eat a lot of meals with the person you're dating, so it's good to know what their go-to Friday night food is. Are they always going to want to order pizza, or do they prefer to order Indian and then spend the weekend living off the leftovers?

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What's Your Guilty Pleasure?

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Does he secretly love watching The Bachelor or does he cry to YouTube videos of soldiers coming home to their families? You never know what you could learn with this one.

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What's At The Top Of Your Bucketlist?

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This one is basically guaranteed to get the conversation going if you're struggling to find something to connect about. Chances are if it's on their bucketlist, it's something they're passionate about, and who doesn't want to talk about something they're passionate about?