225 Deep & Engaging Questions to Get to Know Your Date

So, you just scored a date. Nice! Now comes the fun part—getting to know them. Getting to know someone is a gradual process, but there are some questions you can ask to help determine if you’re compatible. In this article, we’ve compiled over 200 deep, flirty, and funny questions to ask your date or crush, with helpful tips from dating coaches and experts.

Great Get to Know You Questions for Dating

Dating expert Kristina Mirgorodskaya recommends asking about your date’s dreams, what they want to achieve in life, and what they’re looking for in a partner. Here are some specific questions you can ask:

What is your motto for life?
What are you most passionate about?
Do you want children someday?
Are you close to your family?
How do you define happiness?

Section 1 of 10:

Best Get to Know You Questions

Download Article

Ask a wide variety of questions to get to know them. According to dating expert Kristina Mirgorodskaya, some of the best ways to get to know someone you’re dating are to ask about their dreams, what they want to achieve in life, and what they look for in a partner.^{[1]
X
Expert Source

Kristina Mirgorodskaya
Dating Expert

Expert Interview} Sprinkle in some fun, lighthearted questions to keep the conversation flowing. Here are some examples:
- What is your favorite time of day and why?
- What cheers you up?
- What are some positive things that have happened in your life recently?
- What would I be surprised to learn about you?
- What is one of your favorite quotes?
- Of everyone living and dead, who would you most like to have dinner with?
- What is your motto for life?
- What’s one thing you’re looking forward to this year?
- If you could be anywhere, doing anything right now, where would you be and what would you be doing?
- What is a modern convenience you could not live without?
- When was the last time you did something for the first time? What was it?
- What book has had the greatest impact on your life?
- Where is the next place you want to travel to?
- What is your favorite place on earth?
- If you could live anywhere in the world, where would it be?
- What’s the most spontaneous thing you’ve ever done?
- Are you more introverted or extroverted?
- Which fictional character are you most like?
- How do you like to unwind after a long day?
- What’s your go-to comfort food?
- Do you enjoy cooking, or would you rather eat out?
- Are you a morning person or a night owl?
- If you could time-travel, where and when would you go?
- Do you have any weird or funny family traditions?
- What’s your favorite way to make someone laugh?
Meet the wikiHow Experts

Kristina Mirgorodskaya is a dating coach and the marketing director of Amiccio, a New York City social app that helps singles make new connections.

Imad Jbara is a dating coach for NYC Wingwoman, LLC, a relationship coaching service that offers matchmaking, wingwoman services, and 1-on-1 coaching for singles.

John Keegan is a dating coach and motivational speaker based in New York City. He has over 15 years of professional experience.

Lauren Sanders is a professional matchmaker, dating coach, and the founder of Dating for the Soul. She has over 4 years of experience and specializes in helping singles find love.

Renee Slansky is a dating, relationship, and life coach based in Europe. She has contributed her expertise to several publications, including The Huffington Post, The Good Men Project, and Marriage.com

Section 2 of 10:

Deep Get to Know You Questions

Download Article

Dig a little deeper than small talk. Dating coach Imad Jbara recommends “building emotional connections on the first date because it makes you want to see that person again.”^{[2]
X
Expert Source

Imad Jbara
Dating Coach

Expert Interview} Don’t be afraid to go a little deeper than asking their favorite color. Asking deep questions shows them that you have an actual interest in getting to know them. Here are some examples:
- What are some of your goals for the next year?
- If you could rid yourself of one bad habit, what would it be?
- What would you do differently if you knew nobody would judge you?
- What are you most passionate about?
- What’s one thing you love that you get to do almost every day?
- Who do you look up to and why?
- If time and money were no issue, what would you do with your life?
- What are your strengths and weaknesses? How are you growing in them?
- Wealth or love?
- Knowledge or power?
- What’s an obstacle you’re afraid of facing but that you’re going to do anyway?
- If you could go back and change something about your life, what would you do differently?
- What’s the best advice you’ve ever received?
- If tomorrow were your last day on earth, what would you do?
- What do you like most about yourself?
- What motivates you?
- What do you like to do when you’re alone?
- If you could tell yourself from 10 years ago one thing, what would it be?
- What’s the worst lie you’ve ever told?
- What’s something you learned way too late in life?
- Where do you see yourself in 5 years?
- What’s your biggest career aspiration?
- If you could go on a personal retreat, what would you do?
- Would you ever consider a long-distance relationship?
- How do you define happiness?

Section 3 of 10:

Flirty Get to Know You Questions

Download Article

Ask playful questions to flirt with your crush. When getting to know someone, dating coach John Keegan recommends asking cute and playful questions to show you’re interested.^{[3]
X
Expert Source

John Keegan
Dating Coach

Expert Interview} For example, ask them about their idea of a perfect date and tell them you’ll keep their answer in mind for next time. Here are some other flirty questions to ask:
- What’s your ideal date?
- What’s your love language?
- If you had fewer inhibitions, how would you behave differently?
- What are some of your favorite compliments to receive?
- What made you ask me out/agree to go out with me?
- Do you like pick-up lines?
- Do you prefer to pursue or be pursued by your romantic interest?
- Where are you most ticklish?
- Where is your favorite place to be kissed?
- If my answer was yes, what would your question to me be?
- Do you believe in love at first sight?
- Who was your first celebrity crush?
- Which fictional couple do you think we’re most like?
- What’s your perfect romantic getaway?
- When is the last time someone made you blush?
- How direct would you want someone to be if they had feelings for you?
- What’s the top song on your makeout playlist?
- Little spoon or big spoon?
- What first attracted you to me?
- Know any other good, flirty questions? Share them in our “What are some flirty questions to ask a guy?” or “What are some flirty questions I can ask a girl?” forums!

Section 4 of 10:

Funny Get to Know You Questions

Download Article

Make them laugh with some silly questions. When getting to know someone, it’s also important to get to know their sense of humor. After all, a lot of people want a partner who can make them laugh!^{[4]
X
Research source} Here are some funny questions to ask on your next date:
- If you won the lottery, what would you do with the money?
- What could you give a 5-minute presentation on with no preparation?
- How would you describe the internet to a caveman?
- If you could host a talk show, who would be your first guest?
- What was your favorite Poptart flavor growing up?
- Bungee jumping or skydiving?
- What’s your favorite dad joke?
- If you joined the circus, what would your act be?
- What’s the worst food you’ve ever eaten?
- If you could live in any sitcom, which one would it be?
- How long do you sit at a green light before honking at someone?
- What’s your most embarrassing moment?
- What’s your go-to karaoke song?
- You’re on a desert island. What book, piece of clothing, and food item would you bring?
- If you were Miss America, what would be your platform?
- What’s the funniest pick-up line you’ve ever heard?
- Clowns? Yea or nay?
- If you had to give up one of your 5 senses, which would it be?
- Which animal would you like to have a conversation with?
- Have you ever had a run-in with the law?
- If your life were a TV show, what would the theme song be?
- What is your Roman Empire?
- If you had the chance to go to outer space, would you do it?
- Would you rather have a personal driver or a personal chef?
- If a genie gave you 3 wishes, what would you wish for?

Section 5 of 10:

Questions to Get to Know Their Past

Download Article

Learn how their past has shaped who they are today. To get to know someone, matchmaker and dating coach Lauren Sanders believes it’s important to ask about their family history and where they come from.^{[5]
X
Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Consider asking about their previous romantic relationships, as well, to learn more about what they’re looking for. Here are some questions to try:
- Have you ever been in a serious relationship?
- What’s the longest relationship you’ve been in?
- Why did your last relationship end?
- How did you meet your best friend? What are they up to now?
- What is one of your favorite holiday memories?
- What job did you want to have when you were a child?
- What were your favorite books as a child?
- What’s something you learned from your last relationship?
- What’s something you’ve learned from being single?
- Are you friends with any of your exes?
- What has your dating experience been like?
- What were you like as a kid?
- What’s your favorite childhood memory?
- What is your favorite thing about where you grew up?
- If you could relive one day from the past, which would it be and why?
- What’s your biggest regret, and what did you learn from it?
- When was your first kiss?
- Who was your first kiss with?
- What’s your earliest memory?
- What was your favorite age growing up?

Section 6 of 10:

Vulnerable Get to Know You Questions

Download Article

Ask intimate questions to deepen your bond. If you’ve been on a few dates, it may be time to start building intimacy and getting to know the person you’re seeing on a deeper level. If you’re both comfortable, ask some vulnerable questions to get them to open up. This is a great way to bond and find out if you’re emotionally compatible. Here are some examples:
- What’s something you’re afraid of?
- How would your parents describe you?
- What’s something that often triggered you in your previous relationships?
- What’s your perspective on exes remaining friends after a breakup?
- What do you need to feel supported?
- What helps you feel safe, loved, and protected in a relationship?
- What do you think about therapy?
- When was the last time you cried, and why?
- What is something you worked hard for and still didn’t get? How did you handle that loss/disappointment?
- What is something you’re unsure about in life that you’re okay with being unsure about?
- What is something you get in your head about?
- Would you change anything about your personality?
- Who knows you best?
- What does it take for someone to become good friends with you?
- What’s something you think is often misunderstood about you?
- How do you handle stress or pressure in your life?
- When have you felt most alive?
- What are you struggling to let go of?
- What do you need to forgive yourself for?

Section 7 of 10:

Questions to Get to Know Their Values

Download Article

Find out what’s truly important to them. It’s okay (and totally normal) to not have everything in common with your partner. However, to have a healthy relationship, you usually have to have similar values, including things like what you want out of life, political views, and religious views. “It’s always important to ask how they feel about children,” adds Sanders.^{[6]
X
Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Discover what your crush values most by asking these questions:
- What are some of your most prized personal possessions?
- What’s something you’ve never done but want to do before your life ends?
- What is something you’ve done or made that you are proud of?
- What are your favorite things to spend money on and why?
- Do you want to get married someday?
- Do you want to have children someday?
- What qualities do you value in a romantic relationship?
- What’s your preference for paying at the end of the date?
- What social issue do you care about most?
- What role do your friends and family play in your life? Do you have a close relationship with them?
- Who would you consider your support system?
- What’s your approach to work-life balance? Is that important to you?
- What are your views on gender roles and stereotypes?
- What are the top 5 qualities you look for in a friend?
- If you had one extra hour of free time a day, how would you use it?
- How do you define success?
- If you could own a house or travel the world, which would you choose?
- What’s the best gift you’ve ever received?
- What do you think about women proposing to men?
- Are you more of an optimist or a realist?
- Do you consider yourself religious or spiritual?
- Do you believe in God?
- What do you think makes someone a good person?
- How can someone earn your trust?
- How can someone lose your trust?

Section 8 of 10:

Basic Get to Know You Questions

Download Article

Get to know the basics first. While it’s important to discover if you’re compatible, dating coach Renee Slansky recommends that you “keep it casual in the beginning.”^{[7]
X
Expert Source

Renee Slansky
Dating Coach

Expert Interview} Don’t immediately ask your date about their childhood traumas; work your way up to more intimate conversation. Here are some simple questions to help break the ice:
- What do you do for work?
- Where are you from?
- Do you have any siblings?
- Do you have any pets?
- What are some of your favorite movies?
- What do you like to do for fun?
- What are some of your favorite desserts?
- Who’s your favorite musician?
- What’s your favorite holiday?
- What does a typical weekend look like for you?
- What are your top 3 favorite TV shows of all time?
- What’s the last concert you went to?
- What is something on your bucket list?
- Do you have any kids?
- Pancakes or waffles?
- What 3 words would you use to describe yourself?
- What makes you unique?
- What’s a random fun fact about you?
- Do you have any secret talents?
- What is something you want to learn or wish you were better at?
- What are your pet peeves?
- What makes you laugh?
- What’s your favorite outdoor activity?
- What are your 3 favorite smells?
- Do you enjoy traveling?

Section 9 of 10:

Get to Know You Questions About Communication

Download Article

Discover their preferred communication style. Everyone communicates differently, so finding out how your crush or partner likes to communicate can help you avoid or resolve conflict later on. Here are some questions you can ask:
- Do you prefer to text or call?
- How do you show appreciation in a relationship?
- How do you want your partner to show that they appreciate you?
- How do you typically respond if something is bothering you?
- At the beginning of a relationship, how often do you like to talk to the person you’re getting to know?
- How often do you want to see each other in person?
- How often do you see your close friends?
- Do you hold grudges or let go of things easily?
- Do you tend to yell when you get frustrated?
- How often do you give people the silent treatment?
- In an established relationship, do you expect to communicate every day?
- If our relationship were ever long-distance, how would you prefer to communicate?
- How often do you make decisions without consulting your partner?
- How soon in advance do you like to make plans?
- How do you handle jealousy or trust issues?
- How do you envision celebrating milestones and special occasions?
- How much time to yourself do you need in a relationship?

Section 10 of 10:

Questions to Get to Know Their Intentions

Download Article

Learn what they’re looking for in a relationship. If you’re on a first date or talking to someone on a dating app, it’s important to be direct and ask what they’re looking for to make sure you’re both on the same page. These questions will help you figure out if you’re romantically compatible:
- Are you looking for something casual or long-term?
- When dating, do you prefer to get to know one person at a time or multiple people at a time?
- How long do you typically date someone before becoming exclusive?
- What are your deal-breakers and non-negotiables for relationships?
- What are your views on commitment, monogamy, or ethical non-monogamy?
- What are some goals you think we should have for our relationship, and why are those important to you?
- What is your idea of a healthy relationship?
- Would you ever live with someone before you’re married?
- What are your views on abstinence?
- What do you want to get out of your next relationship?
- How long would you want to date someone before you consider marriage?
- Do you believe in soulmates, or do you think love is more about timing and effort?
- How much effort are you willing to put into a relationship?
- Do you know your attachment style? If so, what is it?
- How important is physical intimacy to you in a relationship?
- How do you feel about divorce?
- How soon do you trust someone in a relationship?
- Do you fall in love quickly?
- What are your thoughts on casual hookups?
- At this point in time, are you more interested in physical beauty or inner beauty?
- Do you often give people second chances?
- Have you ever cheated in a relationship?
- How important is honesty in a relationship?
- Would you ever consider an open relationship?
- What do you think of age gap relationships?