Flirty Questions to Ask Your Boyfriend

Are you looking for flirty questions to ask your boyfriend? Well, you’re not alone. Women tend to ask their partners lots of questions (I’m guilty of it!). When my husband and I were dating, one of my favorite ways to ask him questions was over text using my Nokia phone and through Friendster.

Nowadays, there are different avenues for texting your boyfriend. You can do it on IG, Facebook, or even create a flirty Tik Tok just for him. Anyway, to make things a little easy for you, I’ve listed several flirty questions to ask your boyfriend and broken them down into different types of texts. Even if you do find some overlaps, make sure you take a look!

Whatever situation you find yourself in, you will always be ready with flirty questions to make conversation with your boyfriend wherever you like. I know what you’re thinking- there’s no way he’s going to know what came over him.

Just scroll down the page to see all the different questions, or use these links to jump to a particular favorite.

Subtle Flirty Questions to Ask Your Boyfriend

I’ve found that subtle questions are great if you want to understand your boyfriend better. You can slip them casually into conversation. Here goes:

What’s the first thing you noticed when you met me? When you’re trying to flirt with a guy subtly, the first thing you want to do is learn how their brain works.
What’s your favorite way to kiss? They’ll know you’re curious and will want to flirt right back. subtle flirty questions to ask a guy
A million dollars is on the line. What would you never do for it? This is an excellent way of learning what your boyfriend’s values are.
What qualities do you find attractive in a girl? Learn what attracted him to you and what you can do to keep him interested.
When did you know that you wanted to date me?
What do you believe in more, destiny or fate?
So, do you think you would make a great boyfriend?
Do you prefer being small spoon or little spoon?
What’s the most romantic thing you’ve done for anyone?
So… any plans for the weekend?
How do you manage to look even more handsome when you get angry?
Do you like kissing in the dark or in the rain?
What color do you think would make you not take your gaze off me?
What would you do to me if I spent the night with you?
Would you cuddle me all night?
Would you make love to me in the dream if you had the chance?
What do you see when you look into my eyes?
Would you give me your love 365 days of a year?
Which of my physical features is your favorite?
Me and you in an empty dark room, what would you do to me?

Cute Flirty Questions to Ask Your Boyfriend

When you’re thinking of cute flirty questions to ask your boyfriend, you want to ask questions that’ll make both of you find a new appreciation for each other. When my husband and I were dating, I always made sure to ask him cute flirty questions that would remind him of the love we shared or how spontaneous I could be. Check these out:

Is it ok if I kissed you right now?
What’s your love language?
How do you know I love you? What does love mean to you?
What’s the first thing you think about each morning you wake up next to me?
Would you shout my name to the whole world and tell them how much you love me?
Is there a song that reminds you of me when you hear it?
We’re eating cookies, and there’s only one left in the jar. Would you give it to me?
What’s something you see me do (that I don’t know about) that you love?
You really have no idea how cute you are, do you?
What would you pick if you had to choose between tea, coffee, cola, and me?
How would you define love in the context of me?
I don’t see it, but do you ever get shy around me?
What would you like to do to me if you could do anything?
What do you hate but had to tolerate because of me?
Would you mind if I kiss you when people are watching?
Why did you choose me out of all the girls in the world?
How do you cope with my troubles and silly behaviors even when I know they get on your nerves?
How do you manage to smile even when things seem tough?
If we strolled down the street and I stopped you halfway, then kissed you for no reason, what would you think?
How would you feel if I told you how much l love you being topless because it excites me?

Random Questions to Ask Your Boyfriend

Random questions you should ask your boyfriend are just that random. I like to think that these are questions you can ask during everyday situations, such as when you’re watching the sun go down or when you’re chilling out by the pool.

What activity do you think we can try out together?
Use three words to describe me
Name two things that will always make you smile
What’s the nicest thing anyone could ever tell you?
Do you have superstitions? Why do you believe in them?
If you could meet anyone, who would it be?
What’s something no one else knows about you?
Would you ask for directions if you’re lost?
What would you do if something happened and I couldn’t speak the same language as you?
Would you tell me if I had spinach or lipstick stuck to my teeth?
Which day is most perfect to be called your ideal day? And why?
What about nature do you love?
Between everyone you care about, who do you have the most respect for?
What would you give me as a birthday gift during my birthday, and why?
What is the most exciting book you’ve ever read?
What subject did you detest the most in high school?
Have you ever been pranked, and what was the outcome?
Do you believe in love at first sight, and have you been in such a situation?
Have you ever been talked down before? What was your reaction?
What kind of person do you think I am?
What is your biggest concern about work?
What do you think about me having male friends?
Would you write me a poem?

Flirty Questions to Ask Your Boyfriend over Text

One time, when my husband and I were still dating and had to cancel our dinner plans because he had to work late, I knew there was more I could do to lift his spirits. So I decided to send him some flirty questions, and after the first one, I knew I had his attention.

Remember that sending an SMS is still one of the best ways to send a text fast. An SMS is an excellent option if you need to send something as fast as possible or if the WiFi went off or there’s a weak signal.

Here are some to help you along your journey.

What would you rather be doing right now if the world was ending tomorrow?
What’s the best compliment I’ve ever given you?
Have you ever had a crush on an older woman? Who was it?
Is there a time you weren’t this attractive?
How deep do you think I’ve fallen for you?
How do you feel when I send you a text message?
Would you rather win the lottery or find the love of your life?
What do you think your friends and family would say about us or me?
Would you be with a girl who hated travel?
Are you a good cook? If yes, would you cook for me?
What do you think about us moving in together?
Why didn’t you tell me you loved me this morning?
Would you make love to me in the dream if you had the chance?

Romantic Questions to Ask Your Boyfriend When You’re Bored

Earlier on, one of my goals in my dating life was never to make my relationship dull. I mean, how often can you ask, “how was your day?” Boring, right? Even if you’re bored, there’s always something to say to get you and your boyfriend talking. So, what about some romantic questions?

Do you miss me when we aren’t together?
Do you mean it every time you say, “I love you?”
What is the one experience you’d like to share with me?
Can I call any time I want to hear your voice?
What’s the best thing about being in a relationship with me?
Do you see me in your future?
What is the most romantic thing you’ve done for someone?
Do you believe in soul mates or love at first sight?
What do you think we should do to make our relationship last?
Do you imagine me next to you when you’re alone?
Do you have goose bombs when you hear my voice?
Would you leave your friends and favorite game to spend time with me?
Do you see me in your future?
Where is your dream travel destination?
Can you cook?
What’s something ridiculous you’ve always thought about me?
What’s one thing you’ve been dying to tell me?
What rumors about me that you’ve heard?
Dinner at home or outside?
What’s your last thought about me?

Funny Questions to Ask Your Boyfriend

Sometimes, all you need are funny and flirty questions to ask your boyfriend to make him laugh. I believe couples that laugh together form the most extraordinary bonds and will always be able to see humor even in the darkest of days.

If I was a really fluffy bunny, what would you name me?
Tell me about your most embarrassing moment
What’s your favorite cartoon character and why?
What’s the worst thing you’ve said to a girl you were attracted to?
Has anyone ever walked in on you while you were using the bathroom?
What’s the worst pickup line you’ve ever used?
Are you up to running in the nude?
Who do you think is the funniest person in your life? Why?
If you could eat anything with a side of chocolate, what would it be?
What’s your most useless skill?

Freaky Questions to Ask Your Boyfriend

No doubt, freaky questions should have been top of the list of flirty questions to ask your boyfriend. When you’re asking these questions, try not to be shy because they’ll help you know your boyfriend at a deeper level. Here we go.

Do you subscribe to “a lady in the streets but a freak in the sheets?”
Bare or hair down there?
Tell me about the freakiest place you’ve had sex?
If I were with you right now, what would you do? I need details.
Would you get me lingerie as a surprise gift?
Tell me what you think about a girl making the first move?
Have you ever been in a FWB (friends with benefits) situation?
What freaky thing do you think we’d do if we got drunk together?
When I walk away, do you check me out? Do you like the view?
If you couldn’t have me, who would your dream girl be?
How would you feel if l turned up one day at your workplace wearing a wedding dress?
What would you do when you turn on the radio and hear me call in and dedicate a song to you live on air?
Can you tell me ten reasons why I am better than all the girls you have ever been with?
What silly thoughts have you had about someone you shouldn’t?
What was your most memorable dream involving me?
Would you sing me love song?

Dirty Questions to Ask Your Boyfriend

If you and your boyfriend have already been to the bedroom, then at some point, you’re going to think about dirty questions to ask him. Knowing you can turn your man on just by asking him a question is a powerful feeling. However, you don’t want to take advantage of it when the time or occasion isn’t right.

Would a nude picture of me turn you on?
Do you think about me when you’re touching yourself?
What part of my body turns you on the most?
What’s your record for the most number of times you had sex in a row?
Would you like to watch me pleasure myself? Would you like me to watch you?
Are you open to trying out toys in the bedroom?
If I were next to you right now, what nasty thing would you whisper into my ears?
According to you, what’s the sexiest part of my body? Would you like to kiss it?
How did it feel the first time we made love?
Would you like to try some of my edible underwear?
How good or bad am I in bed? Rate me over ten.
How did you feel when we first made out?
What’s your most sensitive spot?
What nightgowns do you prefer I wear at night?
What new things would you be open to trying in bed with me?
What is your favorite location for sex indoors?
Would you mind making love to me on the balcony?
What would you do if I lie next to you naked?
My breast or butt, which do you love the most?

Serious Questions to Ask Your Boyfriend

I don’t know about you, but I think it’s always an excellent idea for you and your partner to be on the same page regarding the direction of your relationship. Even when you’re thinking about flirty questions to ask your boyfriend, it’s ok to incorporate some serious ones so you can know your partner better.

To do this, you will have to get down to business and prepare great questions. Here are some examples that will guide you along.

How long was your last relationship? Why did it end?
Have you cheated on a partner before?
Are you over your previous girlfriend?
Is spirituality or religion an essential part of your life
Have you been married or engaged before?
Have you gotten anyone pregnant in the past? How did you handle the situation?
Have you ever spent the night in jail?
What are your bad habits?
If we were living together and were sharing expenses, what would you do if I lost my job?
Have you ever been tested for HIV or another STD?
Have you had kids with someone else before me?
Have you ever cheated on me with anyone before?
How often do you experience mood swings?
Can you trust me with your male friends?
What is your take on faith, or how important is faith to you?
How do you picture us in years to come?
Have you attempted hurting anybody before, and why?
What are your fears about marriage?
Have you ever thought of cheating on me?
Will you still love me the way you do now in a few years?

Truthful Questions to Ask Your Boyfriend

One of the essential aspects of any relationship is communication. Where there are communication issues, a relationship may start to break down. Some of the questions I’ve listed before will help you and your boyfriend develop a better relationship.

Are you happy with our relationship presently? If not, why and how can we deal with it?
Do you think we’re making a positive impact on each other?
Do you think we fight fairly and maturely?
I feel like we’re enabling each other’s bad habits. Do you think the same way? What can we do about it?
Do you feel appreciated when you’re with me?
Do you get satisfied when we have sex?
Is there anything about our relationship you’d like to change?
When do you think I challenge you most?
Since we started dating, have I changed? Is it a good or bad change?
Are there things/people you had to sacrifice to be with me?
Who has had the most impact on your life?
Which friends of yours do you trust the most?
Do you have trust issues?
Have you experienced heartbreak before?
Do you tolerate lies? What will your reaction be if you discover I’ve ever lied to you?
Are your smiles for me always genuine?
How much do you sacrifice to make me happy?
If you had the chance, would you still choose me to be yours?
Do you love my cooking or being cautious of my self-esteem?
What turns you off about me?
Do I nag too much?
What do I do that gets on your nerves?
Do you still think of your ex, even occasionally?
Am I enough for you?
Do I have everything you need in a woman?

Questions to Ask New Boyfriend

When you have a new boyfriend, you want to learn as much as you can about him. So, what’s the best way to do this? Ask questions, of course! BUT, what questions should you ask your new boyfriend so you don’t risk chasing him off before your relationship even starts?

Some of the questions I recommend you ask may seem a little serious. But, if you’re looking for a serious relationship, you should ask them so you know what you’re getting yourself into.

What’s your love language?
Have you cheated on a partner before? How have you worked on yourself to ensure you don’t do it again?
Are you over your previous relationship and girlfriend?
Do you have anger issues?
What do you think about LGBT rights?
Are you comfortable being in a long-distance relationship?
Have you ever been physically, verbally, or emotionally abusive in a relationship? If yes, what have you done to change that?
What’s the kindest thing you’ve done for someone you were in a relationship with?
Where are you from originally, and where else have you lived? What was your favorite place to live?
What are some significant events in your past that have contributed to the person you are now?
Do you in any way still think about your ex?
What led to your last breakup?
How long was your last relationship?
How’s my name saved on your phone?
How long have you had a crush on me?
What’s that one thing you cannot do for me?
What is one thing about me that you dislike?
What’s one thing that attracted you to me?

BONUS QUESTIONS

Subtle Flirty Questions to Ask a Guy

When you’ve just met a guy, and you want to know him better, you can ask him subtle but flirty questions. These questions are for that guy who hasn’t transitioned into a boyfriend yet.

What do you first look for in a girl?
So, do you have a crush on anyone?
What is your type?
What would be your reaction if I told you how hot you are?
Describe yourself in three words?
Now, try to describe me in three words?
Have you been skinny dipping? If no, would you ever?
Tell me about your very first date?
Tell me about the weirdest place you’ve hooked up with a girl?
Do you prefer to talk on the phone or text?

Flirty Questions to Ask a Guy On Text

When I was still in the dating scene, I knew there were questions I could ask face to face and those I could ask over text. Here are some of the questions I loved asking on text to keep a conversation going with a crush.

What’s your idea of an ideal date?
Name three things that will always make you smile?
What makes you laugh every single time?
What’s the craziest date you’ve been to?
Do you like dancing? Are you good at it?
Tell me about the person you look up to most?
What’s the meaning of your name?
Tell me about your first crush. Why drew you to her?
What’s your favorite thing to do on holiday?
Tell me about your biggest pet peeve?

Flirty Questions to Ask a Guy on Tinder

So you’ve got a new crush on Tinder! If you’re like me, you must be looking forward to late-night texts, lots of flirting, and awkward but cute moments. Now is the time to get to know each other. Here are some questions you can ask your crush.

Would you go out to dinner with me?
Would you be ok with a girl making the first move?
What’s the one thing you’re dying to ask me?
Have you ever fantasized about me?
What’s the one thing you’d do over and over again?
Is there anything specific you’re looking for in a relationship?
What’s the best gift you’ve ever given?
What are you terrible at?
What’s your Myers-Briggs
Tell me about one thing I wouldn’t think to ask but should know about you?

Don’t Be Lost For Words

Next time you’ve got no idea what to say to your boyfriend, man crush, or potential partner, you can use the list of flirty questions to ask your boyfriend I’ve set up above. Not only will you up to your dating game, but you’ll also be able to know your partner better!