If You’re Dating Someone New, You Should Ask Them This – Questions To Truly Get To Know Someone

emiliegardham | November 9, 2024 9:00 am

Dating is super stressful, especially those first few times you hang out and you're still getting to know each other. It can be hard to know what to talk about and those awkward silences can seem like they're going to doom your potential new relationship.

These are some questions you can ask your date to fill those silences and to get to know them better.

When You Were A Kid, What Did You Want To Be When You Grow Up?

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Unsplash / Michał Parzuchowski
Unsplash / Michał Parzuchowski

It can be fun talking with someone about their childhood, or how much they've changed since they were a child. You'll get to know things about them like their hobbies and interests.

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What Is Something You Wish You Were Better At?

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Photo Credit: Unsplash / David Pennington
Photo Credit: Unsplash / David Pennington
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Everyone has something they wish they were better at and finding out what your date is wanting to know more about can be really telling. It shows self-reflection and what they think are important skills worth improving.

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What Song Could You Listen To On Repeat For The Rest Of Your Life?

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Unsplash / Adrian Korte
Unsplash / Adrian Korte
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Music taste is so important! You don't have to like all the same music, in fact, it will be more interesting if you don't. But knowing what bands someone loves is a great way to get to know them.

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What Is Your Dream Vacation?

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S'well/Unsplash
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Does he want to go sit on a beach or take a tour across Europe? These are things you want to know so you can daydream about your future vacations together.

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What Are Your Pet Peeves?

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Unsplash / Frankie Cordoba
Unsplash / Frankie Cordoba
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Finding out the things that annoy someone will help you see into who they are. It will also give you a chance to let them know what your pet peeves are so you know how to avoid annoying each other.

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What's The Last Thing You Binge-Watched?

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Photo Credit: Unsplash / Thibault Penin
Photo Credit: Unsplash / Thibault Penin
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At the very least, you'll get a great Netflix recommendation from your date. You have to know if you are interested in some of the same things so you know if this is someone you can snuggle up and watch your stories with.

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What Are You Afraid Of?

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Photo Credit: Unsplash / Mark Flanders
Photo Credit: Unsplash / Mark Flanders
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I know this question seems really deep, but it's an interesting one. People are afraid of all sorts of things, and starting to make space for vulnerability in your relationship is important.

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What Are Your Love Languages?

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Photo Credit: Unsplash / Djim Loic
Photo Credit: Unsplash / Djim Loic
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Love languages are key! You will have to know how to look after one another. Talking about what you like from a partner and what they like from a partner will help you learn if you're compatible long term.

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How Do You Communicate When You're Upset?

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Photo Credit: Unsplash / Korney Violin
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This is another deep but important question. Everyone deals with their emotions differently and it's important to know what your future partner's boundaries are so you know how to be there for them during difficult times.

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Do You Have Any Pets?

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Photo Credit: Unsplash / Jay Wennington
Photo Credit: Unsplash / Jay Wennington
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This one pretty much goes without saying, and it's vital information. Trading cute stories about your current pets, or the pets you had growing up, is a good way to come back from all that serious talk.

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What's Your Ideal Friday Night?

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Photo Credit: Unsplash / Toa Heftiba
Photo Credit: Unsplash / Toa Heftiba
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You have to know if you both want to stay in on Friday and order pizza, or if they're more likely to want to go out. Then you can make decisions about how much you're willing to compromise when it comes to your free time.

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Tell Me About Your Family?

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Photo Credit: Unsplash / James Besser
Photo Credit: Unsplash / James Besser
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It's nice to know if your date is close to their family or not, or if they came from a big family or a small family. It can be a difficult topic for some people though, so don't push!

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Who Is The Most Interesting Person You've Met?

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Photo Credit: Unsplash / Priscilla Du Preez
Photo Credit: Unsplash / Priscilla Du Preez
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This will tell you what your date finds interesting and also give you a sense of where they've been in the past and the people they had in their lives.

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What Accomplishments Are You Really Proud Of?

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Photo Credit: Unsplash / Muhammad Rizwan
Photo Credit: Unsplash / Muhammad Rizwan
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Give them a chance to boast about themselves. It's nice to hear someone you're interested in talking about something they're proud of. It will start a conversation about what their next goal is and future plans.

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Do You Think You're Introverted Or Extroverted?

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Photo Credit: Unsplash / iam Se7en
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You have to be able to connect on a fundamental level, and that means understanding each other's limits. If you're both extroverted, introverted, or the opposite from one another, knowing that will help you decide if you will be able to make one another happy.

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What Do You Value Most In Your Relationships?

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Photo Credit: Unsplash / Pablo Merchán Montes
Photo Credit: Unsplash / Pablo Merchán Montes
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It's important to make sure that your values line up. It will also give you some insight into their past relationships and things they might have grown through with past partners.

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What Are Your Favorite Foods?

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Photo Credit: Unsplash / Brandless
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If you can't enjoy eating together, then you might as well not be together, right? Is this someone who is gonna enjoy cheat days with you and eat lots of chicken nuggets or is he more of a chicken breast with no seasoning type of guy?

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What Are You Passionate About?

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Photo Credit: Unsplash / Priscilla Du Preez
Photo Credit: Unsplash / Priscilla Du Preez
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This is always a fun topic because you get to see your date be excited about something while they share their passions with you. It's a good question to ask because it will help you see if they know themselves well or not.

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Tell Me About Your Best Friends?

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Photo Credit: Unsplash / Mike Erskine
Photo Credit: Unsplash / Mike Erskine
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A person is hugely influenced by their friends, so putting in an effort to know things about them before even meeting them will get you brownie points. Plus, they might be people you spend a lot of your time with, so it's good to know, right?

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What Do You Like Best And Worst About Yourself?

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a couple talking
Photo Credit: Unsplash / Alex Holyoake
Photo Credit: Unsplash / Alex Holyoake
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This is another question that will help you get to know the person you're dating in a more intimate way. It's a good way to see if there might be any red flags you want to look out for.

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What's The Most Embarrassing Thing That Happened To You Recently?

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Photo Credit: Pexels
Photo Credit: Pexels
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If they're able to share a story about an embarrassing moment, it shows you that they're able to laugh at themselves. It can also show that they're comfortable with you if they're willing to talk about something that wasn't their proudest moment or wasn't their best side.

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What's A Political Issue You're Passionate About?

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Photo Credit: Unsplash / Michelle Ding
Photo Credit: Unsplash / Michelle Ding
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You might not want to dive into who they voted for in the last election, but you could touch on political issues. See what big issues are important to them, or what causes they're informed about or have an opinion about.

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Do You Like To Stay In One Place For A Long Time?

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Photo Credit: Unsplash
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If you're looking to be in a relationship with someone and have a future with them, it's good to know if they're planning on staying where you currently are. Some people are happy to stay in one city for their entire lives, others know that in a few years, they'll want to move on to another location. You have to be aligned on something like this if you want to make a relationship work.

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What Do You Think Is Always A Good Way To Spend Money?

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Photo Credit: Unsplash / Clay Banks
Photo Credit: Unsplash / Clay Banks
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Money is one of the main things that couples can disagree on. If you don't value money in the same way that your partner does, it's going to lead to a lot of arguments and could easily lead to the end of whatever relationship you are building.

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Who Are The Most Important People In Your Life?

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Photo Credit: Unsplash / Dimitri Houtteman
Photo Credit: Unsplash / Dimitri Houtteman
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Are they someone who is super close to their family and talks to their mom every Sunday night, or is their childhood best friend the person that they turn to in any difficult situation? Pay attention to how they speak about the people closest to them.

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What Reality Show Would You Like To Compete On?

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Photo Credit: Amanda Edwards/Getty Images
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You might not think it would, but asking this could tell you a lot about someone—plus it can be pretty fun. Do they want to compete on The Amazing Race because they love to travel and are looking for adventure, or are they incredible at pub trivia and think they could dominate an episode of Jeopardy?

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What Makes You Unique?

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You don't want to be with someone who's cocky or full of themselves, but confidence in yourself is healthy. Asking someone what makes them unique or special can show you if this person knows their worth and what they bring to the table.

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What's The #1 Thing On Your Bucket List?

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Photo Credit: Pexels / Daya Mb
Photo Credit: Pexels / Daya Mb
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They're not required to have a literal, physical bucket list ready to discuss at any moment, this is a good way to learn about what kind of adventure or excitement they're looking for. Is skydiving the top of their bucket list, or are you about to embark on a relationship with someone who's always wanted to run a marathon and might drag you along on runs on a Sunday morning?

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When Are You At Your Happiest?

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Photo Credit: Pexels
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Depending on what kind of person they are, their happiest moments might be when they're surrounded by their friends on a Thursday night, or it could be when they're curled up at home on a Sunday by themselves.

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What's Your Biggest Regret In Life?

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Photo Credit: Unsplash / Marcos Paulo Prado
Photo Credit: Unsplash / Marcos Paulo Prado
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Right off the bat, this question can show you if they're someone who holds onto things for a long time. Maybe they come back to say "I don't have any regrets," or maybe they deeply regret their decision to marry that girl at recess in the second grade.