13 Clever Questions To Ask On A First Date, Because You're So Over The Basic Ones
by Christy Piña

"Ah, yes. Another first date where I'm obligated to ask the same 10 questions I've asked on my last eight first dates. Wonderful." Everyone else who's felt this way about a first date, please say "Aye." Awesome, now that we're on the same page, I have incredible news for you. Your first-date questions don't have to be the ones you recycle through every time. There are clever questions to ask on a first date that'll make your next one seem like less of the same old, same old, and more of the new, new.

But before we get to that, let's talk about first dates for a second. Why are they so awkward sometimes? And why are some people really good at them, while I'm here struggling to find the right words, and when I finally do, they come out all mumbly? For those of you who love meeting new people and don't feel any awkwardness at all during a first date, mad props. I envy you. To those who dread small talk and just want to get to the part where you talk about ~real~ things and ride off into the sunset together on a white horse, I'm right there with you.

Unfortunately, since the person you're going on the date with may not want to jump right into talking about the serious things in life, like why they are the way they are and how their childhood contributed to that, these clever questions can serve as a happy medium for both of you. You get to talk about more than just the weather, and they don't have to jump right into their deepest, darkest fears. See for yourself.

Do You Consider Yourself An Extrovert Or An Introvert? And Which One Do People Consider You?

Distinguishing how people see me and how I see myself is something I always find interesting. To a lot of people, I seem like an extrovert, but I personally consider myself an introvert in most situations.

Learning about how your date sees themselves, versus how other people see them, can help give you an understanding of their actual nature.

What's One Thing That You're Looking Forward To Next Week?

Instead of the typical, "What do you do in your free time?" question, asking your date what they're looking forward to doing next week can give you a broader understanding of their hobbies. It can also tell you what makes your date feel excited, all while giving you a look at their day-to-day life. Talk about multi-faceted!

What's On Your Bucket List?

I'll be the first to admit that some of the things on my bucket list are for my eyes only. Don't get me wrong, I wouldn't mind sharing a few of the items I'm anxious to check off, but not all of them. I'd be interested to see what someone else strives to do in their life, too.

If You Could Visit Any Time Period, What Would It Be?

The 1920s! (And yes, that's because of The Great Gatsby. Sue me.) What about you?

Where Do You Consider "Home"?

Now, this question could be a trigger for someone who maybe didn't have the best life growing up, so use your best judgement before you ask. Bringing this up too early on may not go well, because for lot of people, it's not as simple as 221B Baker Street.

Try to get a feel for the date, and see where your conversations have gone. Have they been very on-the-surface? Have they actually gone deeper than you expected for a first date? If you think they wouldn't mind answering more personal questions, by all means, go ahead and ask them about home. But, if you feel like it may be too much too soon, don't. Trust your gut.

What Was The Last Thing You Bragged About?

Everyone's allowed to brag a little every once in a while, but there are boundaries. If all your date does is brag, it's not cute. Learning what someone brags about shows you what it is they pride themselves on, which, in turn, can give you an idea of the things they value in their life.

What Dating Advice Would You Give Your High School Self?

Oh god, I don't even want to think about high school me. (I wore bows in my hair on the daily, just think about that.) I dated a few different guys in high school, and there are definitely plenty of things I wish I would've known then. Like maybe, "Don't go back to that guy who you clearly don't have feelings for." Or maybe, "Don't take advantage of someone else's feelings." This question allows you to see how your date has evolved and matured since high school, or, on the flip side, whether or not they even have. If your date still acts like they did in high school, ask yourself if that's what you want in an SO.

What Should I Know About You That I Would Never Think To Ask?

This may or may not be a deal-breaker. Your date may say something that they don't think is a big deal, but to you it very well could be. Proceed with caution.

Ten years ago, Where Did You Think You'd Be Today, And Are You There?

Ten years ago, I'm pretty sure I wanted to be a veterinarian, and then five years ago, I wanted to be a surgeon. (Thanks, Grey's Anatomy.) Today, I'm neither of those things. I'm a writer, and I'm happy about where I am right now. It would be interesting to see where my date wanted to be, where they are now, and if they want to be somewhere else down the line.

If You Were A Book, What Would Your Synopsis Be?

This question is basically the same as, "Tell me a little bit about yourself," but I really like how it's worded. It forces your date to get creative and to paint their life in the most picturesque light, all while keeping it short and sweet. Sounds like a challenge, doesn't it?

F*ck, Marry, Kill: Food Edition

Bringing back this classic favorite is the perfect way to break the ice between you and your date. It's lighthearted and fun, and can help the two of you warm up to each other a bit. Give your date three types of food they adore, and make them choose which one they'd f*ck, marry, or kill. It seems a little strange, but the nostalgia is real. Plus, knowing where they'd put pizza on this list is crucial to the success of your future. (Kidding. Kind of.)

What Would Be Your 'Shark Tank' Idea?

By asking your date what their Shark Tank idea would be, you might get a glimpse into their creativity. This could be helpful in planning future dates, because you have a good sense of what they're into! Not to mention, if they ever get on Shark Tank one day, you heard their brilliant idea first.

Would You Rather Fight A Horse-Sized Duck Or 100 Duck-Sized Horses?

And finally, the most important question, clearly. Which would you rather?

If you've had the same first date over and over and you want to change it up, consider asking these questions next time, instead of the typical, "Where are you from?," "What do you do in your free time?," and "What kind of music do you listen to?" questions. While those get the job done, and you do get to know someone's basic facts, the 13 clever questions above will most definitely make your evening 100 times more fun! Try them out. Your date will thank you.

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