60+ Flirty Questions to Ask Someone You Like on a First Date

Questions to ask someone you like on a first date: First dates can bring both excitement and nervousness.

You want to make a great impression and get to know the other person in a fun, engaging way.

Having some playful questions prepared makes for a natural conversation flow and helps build comfort and attraction.

In this article, we’ll check out over 60 flirty question ideas perfect for a first date scenario.

They touch on fun topics like favorite activities, interests, opinions, and lifestyles while also teasing out more about passions and what draws you closer to a potential new partner.

Having questions on hand takes the pressure off performing and lets chemistry unfold.

So read on for some great conversation starters to bring out each other’s smiles and keep learning more all date long!

Read Also: 250+ (Not Boring) Questions to Ask to Get to Know Someone Better

Flirty Questions to Ask Someone You Like on a First Date

60+ Flirty Questions to Ask Someone You Like on a First Date

If you are clueless about questions to ask your date, here are some ideas to get you started:

Warm-Up Questions to Ask on Your First Date

Easing into lighter get-to-know-you topics first helps relax any early date jitters. Try a few of these:

  • What’s your favorite holiday tradition or memory?
  • What music do you listen to when you need a pick me up?
  • What’s your most rewatched TV show or movie?
  • What weird or unique talent do you have?
  • Where is the furthest place you’ve traveled?
  • What’s a hobby you’d love to try if time and money weren’t issues?
  • What’s your favorite comfort food?
  • What would you do if you won the lottery tomorrow?

Fun Questions to Ask Your Date

Sparking smiles and laughter is a great idea too. Tastefully silly queries like these let their personality shine:

  • If you were a superhero what would your power be?
  • What’s the strangest dream you recall having?
  • Boxers or briefs? Silk or cotton?
  • Would you rather time travel to the past or future? When and why?
  • What fictional universe would you most like to visit?
  • What’s the most ridiculous dare you went through with?
  • Do you sing in the shower? Favorite jam to belt out?
  • What’s an odd talent you’re secretly quite good at?
  • If you could choose your birthday cake flavor, what would it be?
  • What’s the weirdest food combo you love to eat?

Deeper Questions to Ask on a First Date

Moving past surface topics shows interest in truly learning about the other. Thoughtful questions like these encourage vulnerability:

  • What’s a childhood memory that still makes you smile?
  • What’s something you’re working to improve about yourself?
  • What inspires you or gives you a sense of purpose?
  • What’s one of your proudest achievements so far in life?
  • What’s your secret dream that you’ve never told anyone before?
  • How would your friends describe your best qualities?
  • What’s a mistake you learned a big lesson from?
  • What’s something about the future you’re excited for?
  • What’s been your most difficult struggle to overcome so far?
  • What makes you feel truly happy and at peace?

Getting to Know You Better Questions to Ask Somone You Like

Now that comfort levels are up, begin exploring interests and what draws you closer:

  • What’s the last great book you read? TV show?
  • What simple things in life do you find the most joy or meaning in?
  • What kind of adventures or new experiences do you seek out?
  • What qualities do you look for in friendships? Romance?
  • Do you consider yourself an optimist or a pessimist? Why?
  • What kinds of dates or activities do you find most enjoyable?
  • What do you like to do on a cozy night in?
  • Do you have any interesting phobias or fears?
  • What’s the most romantic thing anyone has ever done for you?
  • What are your thoughts and feelings on relationships in general?

Flirty Hypotheticals Questions to Break the Ice

Playful hypothetical scenarios inject fun and promote lighthearted connection:

  • If we could combine bodies into one weird Frankenstein-like entity, which parts would you contribute?
  • You’re stuck on a desert island – what three items would you want with you?
  • I’m an alien visiting Earth – quickly, what three things must I experience while here?
  • If you could instantly become an expert in one new skill, what would it be?
  • We’re trapped in an elevator together overnight – how do we pass the time?
  • If you could stop time for an hour, what would you do during that time?
  • You get a message you’re about to turn into the last internet search you made. How screwed are you?
  • I’m a time traveler from the future – what one question can I answer for you?
  • Let’s play a round of “Would You Rather” with fun, silly scenarios.
  • We switch bodies for a day – what’s the first thing you would do as me?

Read Also: 250+ Funny and Interesting Speed Dating Questions to Ask

Learning About Attraction to Ask a Crush

Gauging interest and compatibility involves sharing what you find appealing:

  • What physical traits do you find attractive? Personality traits?
  • What manners or qualities in a date impress you?
  • What’s your “type” when it comes to romance – or do you think types are overrated?
  • What’s something a partner could do that would make your heart flutter?
  • What aspects of a relationship are most important to you – romance, communication, trust, humor, etc.?
  • What non-physical things are sexy to you about a potential partner?
  • What makes you feel truly cherished and cared for by someone?
  • What energizes you and what drains you in a relationship?
  • What are your thoughts on PDA – too much, too little, or just right?
  • What makes you feel close to a date or potential partner?

Fun Hypothetical Dating Scenarios Questions to Ask Someone

Pretend scenarios reveal values and priorities through imagined reactions:

  • I just won the lottery! How would our dating life change?
  • We’re suddenly celebrities for a day – what wild adventure do we get up to?
  • It’s our 1st anniversary and I want to plan a super memorable date – any ideas?
  • I accidentally erased your entire Netflix watch history – how pissed are you?
  • We have to live together under one roof for a month with your family – how do you think it will go?
  • Our friend double booked – we have tickets to your favorite show or game, how do we compromise?
  • If I could pack one celebrity as a third wheel on our date, who would you tolerate best?
  • Instead of eating out, we cook each other a mystery-themed dinner party at home – sound fun?
  • I slept in and we’re late to a wedding – how do you handle the stress?!
  • We’re snowed in cozy at home all day – what’s the #1 activity that sounds perfect?

Questions About Values to Ask Your Date

Shared values indicate relationship potential so it’s helpful to discuss thoughts on important subjects:

  • What political or social issues do you feel strongly about?
  • How do you feel about religion and its role in your life?
  • What are your views on having or raising children someday?
  • How do you balance work, relationships, personal time etcetera?
  • How important is environmentalism or giving back to causes you care about?
  • What’s your definition of success – financial achievements, living vicariously, attaining career goals, etc?
  • What role do friends and family play in your life?
  • Is monogamy important or do you have flexible views on relationships?
  • How do you feel about trying new experiences versus sticking to routines?
  • Do you consider yourself daring, cautious, or somewhere in between?

Questions to Ask When Closing the Date

Bring your first meeting to a lovely end by learning each other’s thoughts on plans:

  • Rate this date 1-10 and explain your rating – any ways to improve the next one?
  • Would you be open to a second date and have any date ideas in mind already?
  • How soon is too soon to plan something versus keeping them guessing?
  • I’d love your number to stay in touch – is now a good time to exchange?
  • Any date no-nos I should avoid if we do meet up again? Things you appreciate?
  • What’s the best way for us to communicate between now and our next outing?
  • Would you be open to something casual or prefer to take things slower getting to know each other?
  • I’ve really enjoyed talking and learning more about you – any last thoughts before we part ways?
  • How do you feel our date compared to your expectations coming in tonight?
  • What’s the latest you’d want to hear from me by to start planning another fun adventure together?


Here are answers to some common questions about first date questions:

What Kinds of Questions Are Too Personal or Intimate for a First Meeting?

Avoid questions about exes, sex history, finances, or heavy political/religious debates. Keep it light, and fun. Focus on interests, values, and chemistry.

How Do I Avoid Awkward Silences on a Date?

Have a few questions handy for every lull. Also, share stories about yourself to prompt follow-up questions.

Focus on enjoying each other more than nervously counting conversation gaps. Small smiles and easy eye contact also convey comfort.

What if a Question Makes the Other Person Uncomfortable?

Be considerate – watch body language and tone. If they seem reluctant to answer, gently change topics.

Your goal is learning what uplifts them, not interrogation. Let conversations flow naturally at their pace too.

How Do I Show I’m Interested Without Coming on Too Strong?

Active listening, eye contact, and an occasional smile show engagement better than non-stop questions.

Complimenting something they revealed about themselves conveys care versus looks. Touch should be minimal (a hug goodbye) unless reciprocated more strongly first.

What if Long Pauses Happen – How Do I Keep Things Positive?

Asking follow-ups to their answers or sharing a related story of your own are great bridges. Compliments, smiles, and questions showing you listened also help.

Suggest moving locations if the chat lulls too much in one place. Stay upbeat and let chemistry develop naturally.

How Do I Exit the Date on a High Note Regardless?

Thank them genuinely for their time. A compliment, another laugh or briefly mentioning enjoying learning about them keeps energy positive.

Exchange contact details and float a potential next activity versus definitive plans. Express hope to see them again and walk away smiling.

Read Also:  270+ Questions To Ask Your Boyfriend

Final Thought

Asking engaging, fun questions is key to getting to know someone new while feeling comfortable.

Learning about interests, values, and what sparks attraction indicates compatibility potential. Focus on truly listening and uplifting the other versus interrogating.

With questions that foster smiles and open up their personality, you set the stage for smooth conversation and decide if you’d like to explore a potential new connection further down the line.

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