Flirty Fun Questions To Ask A Guy

Flirty Fun Questions To Ask A Guy- Boyfriend-Crush-Man

Good communication is the bed rock of every friendship or relationship. But before you get to friendship/relationship stage, one need to know a thing or two about each other which requires some personal and general questions. Having said that, conversations with a guy you admire or you are crushing on can be daunting at times. You may not know where and how to begin. Let help you with some perfect questions to ask a guy you just met to add spice and fun to your next chat!

This list is filled with funny flirty questions to ask a guy during a first date or your boyfriend via text messages to spice up your relationship.

Best Flirty Questions To Ask A Guy

Q:How Do You Know If Someone Is Amazing?
Hint: Find out what’s on their personality shortlist.
Q:Are You Obsessed With Something Right Now?
Hint: Leaning into someone’s hobbies is a great way to get them talking.
Q:Where Is The Best Place To Have A First Date?
Hint: What are interesting questions to ask a guy, you ask? Well, this one’s a great example because you show that you’re valuing their opinion while also creating an opening for an invite.
Q:Have You Been Working Out?
Hint: Let him know you’ve been checking him out.
Q:What’s The Perfect Way To Ask Someone Out?
Hint: This is one of the best questions for your crush because you can get the plays straight from the book!
Q:What’s Your Idea Of The Perfect Date?
Hint: Picnic on the beach or 5-star restaurant?
Q:What Do You Look For In A Girl?
Hint: This is a clear litmus test to see if there is returned romantic interest, making it one of the good questions to ask your crush.
Q:Are You An Introvert Or An Extrovert?
Hint: Even better, what’s his enneagram?
Q:If We Went On A Date, How Would It Go?
Hint: A bold approach, but you can find out quickly if this is a possibility. 
Q:What emoji do you usually use when you’re flirting?

Hint: Kissy face? Wink? Something more creative?
Q:What’s The Most Romantic Thing You’ve Ever Done?
Hint: This is one of the best questions to ask a boy so you’ll find out if your kind of move is even on his radar.
Q:Do You Feel Comfortable With Someone Who Asks A Lot Of Questions?
Hint: Because, spoiler alert, I have 126 more in my back pocket…
Q:Do You Let Your Friends’ Opinions Get In The Way Of Your Relationships?
Hint: If yes, run away, don’t walk!
Q:What Do You Think Is Your Best Feature?
Hint: This flirty question starts the compliments flowing…
Q:What do you think is my best feature?
Hint: And this one keeps the compliment train going, which is why it is one of the best things to ask a guy.
Q:Are You Aware Of How Amazing You Are?
Hint: Get a pulse on what is confidence, and what is vanity.

Fun Flirty Questions To Ask A Guy You Just Met

Q:How Did You Manage To Be Still Single?
Hint: Are there major warning signs here, or…
Q:Do You Like Staying In Or Going Out?
Hint: One of the best questions to ask guys, this will help you find out if he matches your social rhythms.
Q:What Are You Doing For The Rest Of Your Life?
Hint: Is this guy a planner? Or does he see every day as a new adventure?
Q:Are You A Romantic Person?
Hint: There’s no right answer, but it’s good to know what to expect which is why this is one of the best things to ask a guy.
Q:Do Your Weekend Plans Include Me?
Hint: Feel out how much time he’s willing to commit to hanging out.
Q:At What Point In A Relationship Do You Let Your Guard Down?
Hint: Is there a way you can earn his trust?
Q:Pick Two Words To Describe Yourself – What Are They?
Hint: This gives you personal insight really quickly.
Q:Do You Find Yourself More Drawn To Brains Or Looks?
Hint: A balance of both is a totally acceptable answer.
Q:Do You Like Grand Gestures?
Hint: For some people, this is a key way to show affection.
Q:What’s The Most Outrageous Thing You’ve Done?
Hint: We all have our exploits – make sure none of his were super illegal.
Q:What Gift Would Make You Fall In Love With Someone Instantly?
Hint: Another love language key – this could be useful information.
Q:Do You Have Any Passions? What Do You LOVE To Do?
Hint: Focus on him – it’s a great way to get him engaged in conversation.
Q:Where Is The Craziest Place You Have Ever Met Someone?
Q:When You Return Home After A Long Day At Work, How Would You Want To Relax?
Hint: If it’s the complete opposite of your patterns – take note.
Q:If You Could Choose Any Place In The World You’d Like To Be Right Now, Where Would It Be And Why?
Hint: Let’s daydream about living that wanderlust life!
Q:If You Could Spend An Entire Day With Me, How Would It Look?
Hint: Perfect follow up – “It’s not meeting me sooner, right?”
Q:Who Do You Act Nice Around But Secretly Dislike?
Hint: Do they have a frenemy? Let’s make sure to stalk their Instagram.
Q:What Are You Looking For In A Girl?
Hint: When thinking about what are interesting questions to ask, it’s best to ask those that reveal what’s important to him in a partner.
Q:Is There Something I Can Do That Would Make You Hate Me Forever?
Hint: Let’s make sure you stay far away from these triggers.
Q:What Brings Meaning To Your Life?
Hint: What are his core values?
Q:How Often Do You Change Your Opinions Or How You View The World?
Hint: Does he adapt to new information? Or maybe he is resolute…. Let’s just keep away from “stubborn”.
Q:What Excites You?
Hint: If it’s seeing little pet dogs in sweaters then = same!
Q: When’s The Last Time You Felt Butterflies?
Hint: And what caused them?
Q:How Do You Make Sure You Look Good Before Stepping Out The Door?
Hint: Does he have a funny habit? Or maybe he doesn’t check at all and he just hopes for the best?
Q:Do You Think People Treat You Differently When You Dress In Different Clothes?
Hint: This sounds like a fun experiment waiting to happen, so this is definitely one of the best things to ask a guy.
Q:Do You Flip Your Pillow To Feel The Colder Side?
Hint: If he doesn’t, he doesn’t know what he’s missing…
Q:Would You Feel Different About Me If I Sleepwalk?
Hint: Not that there is much he can do about it – but, still. It would be good to get that out of the way if it’s an issue.
Q:Do You Feel Good About Massages?
Hint: Some people don’t like to be touched, and it would be good to know early., before you weird them out.
Q:Are You A Fan Of Movies?
Hint: Maybe he’s into books or music instead.
Q:Where Is Your Happy Place?
Hint: The beach? His grandma’s porch? A spot on a creekside hike? Find out where he resets.
Q:Are You A Fan Of Home-Cooked Meals?
Hint: What are his favorite ones?
Q:Do You Prefer A Pool Or A Hot Tub?
Hint: Or maybe each for different activities?
Q:What Movie Do You Wish Your Life Was Like?
Hint: This is a fun way to find out about his ideal life adventure, making it one of the best things to ask a guy!
Q:If You Could Do Anything In The World, What Would You Do?
Hint: A million dollars a year – what would the game plan be?
Q:Are You Ticklish?
Hint: And where would he say he is MOST vulnerable? Just curious, of course…
Q:What Kinds Of Things Do You Find Repulsive?
Hint: Cockroaches? Loose teeth? Sour milk?
Q:What Are Your Favorite Pet Names?
Hint: Is it classic Rover, or is he more like a George Washington III kind of guy??
Q:What Makes You Easily Flustered?
Hint: Food in his teeth? Forgetting a name? What makes him blush?
Q:Do You Have A Celebrity Crush?
Hint: We all have at least one! Maybe his first and his current?
Q:Would You Rather Be Invisible Or Have X-Ray Vision?
Hint: A classic conversation starter!
Q:What’s something you’re bad at? What’s your favorite thing about yourself?
Hint: Knowing how to laugh at yourself is an important skill.
Q:What’s The Worst Pickup Line You Have Ever Used?
Hint: This can only end in tears of laughter.
Q:What Small Pleasures Do You Enjoy The Most?
Hint: A remote start car? French press coffee? Blankets warm from the dryer?
Q:Are You A Sentimental Kind Of Person?
Hint: Some aren’t, and some people save every grocery list they’ve ever written.
Q:How Realistic Do You Think Couples In Movies And TV Are?
Hint: A fun thought experiment around romance.
Q:Do You Think That Guys Should Always Make The First Move?
Hint: And if he does, why??

Flirty Fun Questions To Ask Your Crush

Q:Between Money And Love, You Would Go For?
Hint: In this day and age, careers often get in the way of romance.
Q:Do You Like Me As A Friend Or Something More?
Hint: This is the DTR conversation – make sure y’all are ready for this step!
Q:Where Is Your Favorite Place To Be Kissed?
Hint: Be specific – the key is in the details!!
Q:What Would You Do If I Kissed You?
Hint: Not, this isn’t only flirty.. it’s also one of the best spicy questions to ask out there.
Q:How Would You Describe Your Perfect Kiss?
Hint: Pro tip = take notes.
Q:Do You Prefer Cuddling Or Kissing?
Hint: Maybe, both?
Q:What Is Your Biggest Turn Off?
Hint: Figuring this out early is a game-changer.
Q:What Did You Think When You First Saw Me?
Hint: Let’s focus on the positives, too…
Q:Do You Believe In Love At First Sight?
Hint: Call it sparks or chemistry – has he felt it before, and did he feel it with you?
Q:Have You Ever Kissed Someone In The Middle Of A Conversation?
Hint: Did it have a good effect?? It probably depends on the conversation.

Intimate Questions Ask A Guy

Q:What Was Your First Kiss Like?
Hint: My guess – awkward!!
Q:Is There Ever A Name You Consider Sexy?
Hint: I bet it ties in with that celebrity crush…
Q:Do You Like When The Girl Makes The First Move Or Would You Rather Be In Control?
Hint: Which is the bigger turn-on?
Q:Would You Ever Go To A Nude Beach?
Hint: Anyone can talk a big game, but how brave is he, really?
Q:Do You Ever Get Shy Around Me?
Hint: Find out how comfortable you make him.
Q:Do You Find Tattoos Sexy?
Hint: And does he have any?
Q:What Do You Wear To Sleep?
Hint: Pajamas? Nothing? Something in between?
Q:Have You Ever Had A Dream About Me?
Hint: Would he tell me if he did?
Q:How Do You Feel About Being Single For A Long Period Of Time?
Hint: Is it refreshing? Lonely? Focusing?
Q:What Type Of Flirting Do You Prefer – Via Texts Or Face To Face?
Hint: Find out what he likes, and what he doesn’t!
Q:Do You Feel Comfortable Sleeping Beside Someone?
Hint: Or is he a sleep-thrasher? It’s time to be honest.
Q:Have You Ever Been Caught Naked By Someone?
Hint: This is sure to lead to funny reminiscing!
Q:If You Were Swimming In Public And Lost Your Trunks, What Would You Do?
Hint: Would he own it or craft a clever disguise?
Q:What Was Your Very First Impression Of Me?
Hint: This is a big question – make sure you’re ready.
Q:If You Could Change One Thing About Yourself, What Would It Be And Why?
Hint: Let’s find out how self-aware he is, and if he has a growth mindset.
Q:Who Was Your First Love?
Hint: This memory often leaves an impression.
Q:Do You Think You Know What Women Want?
Hint: Is he the Romeo he thinks he is??
Q:What Do You Value In A Relationship?
Hint: And, more importantly, are those core values of yours??
Q:Would You Rather Be Called Sexy Or Smart?
Hint: Find out what he wants you to notice about him.
Q:Do You Ever Cry When You Are Happy?
Hint: Follow this up with a question into his happiest memories.
Q:What’s The Most Romantic Date You’ve Ever Been On?
Hint: A thoughtful picnic? Taking a nighttime walk around a lake? Dancing at a hot spot?
Q:What Are Your Dreams And Goals?
Hint: Find out what he thinks about when things get tough.
Q:How Would You Define Love?
Hint: No cheating with Nat King Cole’s description!
Q:When Are You The Most “You”?
Hint: What brings them to life?
Q:Are You Willing To Be Someone’s Shock Absorber?
Hint: What does “holding space” look like for each of you?
Q:Do You Believe Relationships Can Survive Long Distances?
Hint: Let’s get some thoughts around this before it’s a possibility.
Q:Is There Something Crazy That You’ve Ever Dreamt Of Doing, But Never Got The Chance To Do It?
Hint: Trying new things is a great way to build trust and intimacy!
Q:How Long Did Your Last Relationship Last?
Hint: And why did it end?
Q: How Do You Tell If You Are Already In Love?
Hint: When you’re syncing your calendars, you know it’s real.
Q:What Does A Happy And Healthy Relationship Look Like To You?
Hint: Layout some metrics to make sure your relationship stays away from dysfunction.
Q:Does It Bother You If Your SO Asks For Your Social Media Passwords?
Hint: A great way to find out how he feels about trust.
Q:Do You Think Your Family Would Like Me?
Hint: How do they normally react to new girlfriends?
Q: What’s The Most Embarrassing Thing That’s Ever Happened To You When You Were With A Significant Other?
Hint: Make sure to reciprocate with your own embarrassing story!
Q:How Do You Know That You Just Wasted Time In A Relationship?
Hint: Let’s promise not to repeat each of our mistakes.
Q:What Are Some Insecurities You Have?
Hint: Be gentle with this one – this is maybe the most vulnerable question on this list?
Q:What Has Been A Recurring Theme In Your Life?
Hint: Are there specific lessons he has been meant to master?
Q:Has Money Ever Been A Problem In Your Past Relationships?
Hint: With your family, or a girlfriend? How has that shaped his ideas around money?
Q:Would You Change Your Religion Just To Be With Someone?
Hint: How much does spirituality mean to him?
Q:How Do You Feel About Leaving Your Job And Relocating To Another State So You Can Be Closer To Your SO?
Hint: Again, get these kinds of questions out of the way before they are a real issue that has pressure behind it.
Q:Is There Anything That Happened In Your Childhood That Still Has An Effect On You As An Adult?
Hint: Maybe finding out the truth about Santa (being real, of course), or a big move from his childhood home.
Q:Is There One Thing Or Secret That Would Surprise Me About You?
Hint: Make sure to cross your heart that you’ll never, ever tell.
Q:Do You Believe In Destiny?
Hint: How much power do we have to control it?
Q:If There’s One Thing You Could Change About Yourself, What Would It Be And Why?
Hint: Maybe he wants to be taller, or kinder, or a millionaire… or all of the above!
Q:What’s The Best Relationship Advice You’ve Received?
Hint: Mine was – give your partner grace to grow.
Q:What Questions Should Partners Ask Each Other Before Getting Married?
Hint: What are the big discussion topics?
Q:What Do You Think Is The Right Age To Get Married?
Hint: Or is it more about the stage of life?
Q:Do You See Me In Your Future?
Hint: This is a big one! What would that look like?
Q:What Is Your Biggest Regret About Your Love Life So Far?
Hint: Too many girlfriends? Not enough? Was there one that got away?
Q:Are You Hopeful About Your Future?
Hint: What is on the horizon that he just can’t wait to arrive?
Q:How Easily Do You Forgive?
Hint: You’re going to make mistakes – find out how easily he’ll move through them with you.
Q:What Is Something That Scares You On A Daily Basis?
Hint: Is it germs? Or, eeeek, failure?
Q:How Important Is It For Individuals In A Relationship To Maintain Their Own Separate Identity?
Hint: Maybe you can just turn into those people who match each other and their pets.
Q:What Kind Of Memories Do You Want To Make Together?
Hint: Talk about each of your bucket lists.
Q:Do You Think Marriage Is Only A Piece Of Paper?
Hint: Discuss what those vows mean in terms of commitment.
Q:Do You Think It Is Possible That Your Best Friend And Your Spouse Are One And The Same Person?
Hint: This seems like #goals.

Funny Flirty Random Questions To Ask A Guy

Q:What Kind Of Outfit Would You Like To See Me In?
Hint: This one will really get his imagination going. Don’t be surprised if he suggests an outfit that would raise a few eyebrows.
Q:Do You Like It When A Girl Makes The First Move?
Hint: Here’s a hint: most guys love it when a girl makes the first move – and asking this question is probably enough to get his heart pounding.
Q:Do You Have Hidden Tattoos?
Hint: Tattoos can be a real conversation starter – especially when it comes to ones that aren’t visible – at least when he’s wearing clothes.
Q: How Do You Feel About Me Not Wearing Underwear?
Hint: Yep, this is a major “fetish” for a lot of guys out there. Try to say it with a completely straight face, and check out his reaction.
Q:Have You Ever Had A Dream About Me?
Hint: If a guy is serious about you, he has probably dreamed about you in the past. The real question is what happened in his dream…
Do You Like To Be The Dominant Or Submissive Partner In A Romantic Relationship?
Hint: While some guys might not be completely open about their true desires, many others will be surprisingly honest when asked this question.
Q:Do You Want A Picture Of Me Looking Cute Or Naughty?
Hint: Guys love to receive pictures from girls they like, and they’ll appreciate it even more when you ask them this question before you start posing.
Q:What Color Do You Think I Look Best In?
Hint: Some guys really take notice of what you wear, and they can actually be quite useful when you’re figuring out what you look best in.
Q:What Are Your Thoughts About “True Love”?
Hint: Watch him carefully when you ask this question – if he seems lost for words, he might just be in love with you.
Flirty Fun Questions To Ask A Guy
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