When you’re just starting to date someone, it’s exciting but can also be a bit nerve-wracking. You want to get to know each other, but it’s important to keep the conversation easygoing and natural. That’s why we love these dating questions – they’re perfect for sparking conversation without making it feel like an interrogation.
Fun Icebreaker Questions for a First Date
On a first date, it’s important to keep things light yet meaningful. These fun and flirty questions are great conversation starters to get to know your date without making things too serious.
- If you could have any superhero power, what would it be?
- Would you ever be comfortable being naked in public?
- What’s the best gift you’ve ever received?
- If you had to sing karaoke, what song would you choose?
- What’s your favorite movie, and why?
- What’s your dream vacation destination?
- Who is your favorite person in the world?
- What makes you feel most alive?
- What’s the kindest thing anyone has done for you, and why did it mean so much?
- What’s the craziest thing you hope to do someday?
- What’s your favorite ice cream flavor?
- Are you a dog person or a cat person?
- Do you like to plan or go with the flow?
- If I walked into your house, what five things would I notice?
- What’s your favorite type of music?
- What’s the weirdest nickname someone has given you, and why?
- If you could be any animal, what would it be and why?
- If you could live in any time period, which would it be, and why?
- Give me three words that describe you.
Pro Tip: Avoid diving into heavy topics like your dating history on the first date. Keep things lighthearted and save deeper discussions for later.
Questions About Family
Asking about someone’s family can be a great way to get to know them better, but remember to be mindful of their reactions. If they seem uncomfortable, be ready to switch topics.
- Do you have any siblings?
- What’s something fun or unique about your family?
- What did you enjoy doing with your family when you were younger?
- How do you feel about family reunions?
- Does your family have any unusual traditions?
- What’s your favorite family tradition?
- How do you usually spend the holidays with your family?
- Is there anyone in your family you don’t get along with?
- Who’s your favorite family member?
- What was your parents’ relationship like?
- How was your relationship with your siblings growing up?
- Are you close with your extended family or cousins?
- What kind of vacations did your family take?
- What’s your favorite family vacation memory?
- Did your family have any pets?
Questions About Childhood
You don’t have to dive too deep into childhood memories, but these light questions will help reveal a little more about your date’s early years.
- Who was your best friend as a kid?
- Did you have any imaginary friends?
- What’s the weirdest thing that ever happened to you as a kid?
- What’s your happiest childhood memory?
- What kind of student were you?
- Were you part of a clique in school? Which one?
- If your teenage years were a teen drama, which trope would you be?
- What kind of trouble did you get into as a kid?
- What was your first job?
- What was your neighborhood like growing up?
- What games or activities did you enjoy most as a kid?
- What did you want to be when you grew up?
- Could your younger self have imagined your current career?
- What advice would you give your younger self?
- What’s something silly you were afraid of as a child?
Fun Questions to Ask Romantically
Laughter is a great way to build connection, so try some of these funny questions to keep the mood playful.
- Do you have any weird talents?
- Do you know any party tricks?
- If you were a character on a sitcom, what would your catchphrase be?
- Have you ever pulled a prank or been pranked?
- What’s your favorite hot dog topping? And what should never go on a hot dog?
- What’s the weirdest thing you’ve ever eaten?
- What’s your guilty pleasure?
- Are there any TV shows you’re embarrassed to admit you watch?
- How long would you last in a zombie apocalypse?
- What’s your personal theme song?
- What’s the worst smell you’ve ever encountered?
- How do you feel about pumpkin spice?
- What would you nickname me right now?
- Which fictional character do you relate to most?
- If you ran for office, what would your platform be?
- If you wrote a memoir, what would it be called?
- What always makes you laugh uncontrollably?
Light-Hearted Deep Questions
These questions are playful but also hint at deeper topics, perfect for getting to know someone on a more meaningful level.
- Do you believe we’re alone in the universe?
- Do you think aliens have visited Earth?
- Are there any conspiracy theories you secretly believe?
- Have you ever seen a ghost?
- What’s the spookiest thing that’s ever happened to you?
- Do you think you have psychic abilities?
- Have you ever had a dream that came true?
- Who do you think you were in a past life?
- If you could travel to any point in time, where would you go?
- What’s your idea of utopia?
Questions About Careers
For some people, their career is just a way to pay the bills, while others find purpose and passion in their work. Asking about someone’s career can reveal a lot about their values.
- Why did you choose your current career?
- What’s your biggest career achievement?
- Is this the job you imagined yourself doing?
- Is your job just for money, or do you feel a sense of purpose?
- What would you do if money weren’t an issue?
- What’s the best job you’ve ever had?
- What’s the worst job you’ve ever had?
- What job would you never want to do?
- What makes a good boss, in your opinion?
- Have you ever quit a job on the spot?
- What’s the coolest thing you’ve done in your job?
Hobbies & Interests
Talking about hobbies and interests is a great way to understand what truly excites and inspires your date.
- Do you like to read? What’s your favorite book?
- What’s your favorite movie genre?
- Do you play any sports?
- What do you like to cook?
- How do you usually unwind after work?
- Have you ever volunteered for a cause?
- What’s something fun you could teach me to do?
- What’s on your travel bucket list?
- Do you collect anything?
Deeper Questions for a Stronger Connection
When you feel ready to dive deeper, these questions will help you understand your partner’s values and experiences.
- What’s an achievement you’re really proud of?
- What motivates you in life?
- What’s something you wish people knew about you right away?
- What’s your biggest personal struggle?
- What qualities do you value most in a person?
- What would your dream house look like?
- What’s your love language?
Fun Question Games for Couples
Even if you’ve been dating for a while, these question games can keep your conversations lively and fun.
- Dating Game Questions: Ask playful and intriguing questions like they did on the classic game show.
- Would You Rather: Learn more about your partner’s preferences and quirks with these fun, forced-choice questions.
Keep the Conversation Flowing
There’s always more to discover when you’re getting to know someone new. If the conversation ever lulls, dive into one of these questions to keep things flowing!