100+ Questions To Ask Your Boyfriend For a Meaningful Connection

From romantic, dramatic, and fun to thoughtful, here’s a list of 100+ questions to ask your boyfriend and get to know him better!

Apurva Saxena

22 of May, 2025

Nathan McBride - Unsplash

questions to ask your boyfriend — Nathan McBride - Unsplash

Awkward first meet with your to-be boyfriend, and you don't know the right ice-breaking questions to ask him? Or it's been a minute since you two have been going strong, and yet, you haven't asked him questions to test his love? Whatever stage of dating you are in with bae at the moment, asking questions to your boyfriend is a great way to communicate, connect on a deeper level, bond and gain clarity about your relationship.

And not just some relationship-defining questions, we are also talking about the spicy, romantic, juicy kinda questions that will put you both in the mood! Curious? Then you surely are in for a treat. Check out these Qs to ask your boyfriend for A's. Take a look!

Table of Content:

Flirty Questions to Ask Your Boyfriend
Romantic Questions to Ask Your Boyfriend
Spicy Questions to Ask Your Boyfriend
Dirty Questions to Ask Your Boyfriend
Naughty Questions to Ask Your Boyfriend
Deep Questions to Ask Your Boyfriend
Questions to Ask Your Boyfriend to Test His Love
Truth Questions to Ask Your Boyfriend
Fun Questions to Ask Your Boyfriend
Juicy Questions to Ask Your Boyfriend

Flirty Questions to Ask Your Boyfriend

Apart from sending him sweet good morning quotes every day, flirting with your partner is the best way to keep the romance light, cute and exciting. Here’s a list of flirty questions that you can ask your boyfriend the next time you meet, or even over text.

Name a celebrity you'd secretly wish to get hanky panky with.
Me in a beach bikini or a little black dress?
If you have to express how you feel about me right now with a song, which one will it be?
Would you rather kiss me right now or cuddle with me instead?
Would you mind sharing an ice cream cone with me right now?
Do you think about me lying in bed at night? What are your thoughts like?
Rate my lips, ears, nose, eyes and neck from 1 to 5 with 1 being your most favourite.
What makes butterflies flutter in your stomach?
What sexy name would you give and call me by?
What was that one thing about me that attracted you towards me?

Romantic Questions to Ask Your Boyfriend

If your boyfriend shies away from saying ‘I Love You’ or sending you a sweet relationship quote often, dial up these questions to the rescue. Ask your boyfriend these romantic questions and let him say ‘I Love You’ in various ways with his answers.

In a crowd of billions of people, why did you choose me?
If I go missing tomorrow, where would you go looking for me?
If I tell you that I’d like to have a big fat wedding, when you’d prefer a court marriage, how would you settle this dilemma?
How will you make a lazy, hot Summer afternoon at home romantic for us?
Name 5 romantic movies you’d like to watch with me over the weekend.
If you have to describe our future by referring to any part of any movie, what will it be?
What does your ideal romantic date look like?
Do you remember our first kiss? How was it for you?
Will you hold my hand in public or at family gatherings?
What was your initial thought when you saw me for the first time?

Spicy Questions to Ask Your Boyfriend

Gone are the days when you were updating your Tinder bio; it's time to upgrade your flirty questions game and add some spice to it. If you have been through the basic flirty ones, ask these questions next to get your guy’s full attention!

Would you like to see me in black lingerie or red lingerie?
What are you wearing tonight?
If you have to describe how I taste like with a spice, which one would it be?
What will turn you on more - A moaner or a screamer?
If you get to choose your next wet dream, what will it be, starring whom?
What part of the foreplay would you not mind spending more time on?
Would you rather give or take pleasure while having sex?
Are you submissive or dominant?
What’s been your longest record time of mating non-stop?
What’s the dirtiest deed you’ve fantasised about me doing to you?

Dirty Questions to Ask Your Boyfriend

And if the spice is just not enough, go dirtier and ask him those nasty questions that you’ve always had in the back of your mind. This list will help you manifest them correctly. This list is just for some fun! You can refer to this sex questions list if you want more serious answers!

What if I am standing all sweaty in front of you? Will you kiss me?
Makeout inside a tent, camping high above in the mountains? Or make out inside a luxury villa?
If I say “Do whatever you wish with your tongue”, what would you do?
If you have to seduce me with just your words, what will you say?
Good night sex, or good morning sex? Pick one!
What would you like me to search for and watch on an adult website?
If given a chance to resize my bosom, what size would you like me to have?
What should I wear tonight to bed - a towel wrapped around, or your office shirt from today?
If you can lick or kick only part of my body, which part would you choose?
Feisty and rough or slow and soft in bed?

Naughty Questions to Ask Your Boyfriend

If dirty is not your style, these simmered-down questions will also help you get a sneak peek into your guy’s wild side.

We are sitting in public, I look at you, and wet my lips with my tongue. How will you feel about that?
What do you think about bikini wax?
Do you prefer sleeping in your boxers, briefs or going commando?
Sit on your lap or by your side?
Do you like working out in bed, or would you prefer I ride you and sweat it out instead?
What’s been your longest dry run without having sex?
Would you ever like to go skinny dipping with me?
What if we accidentally get locked inside a room for a few hours? How will we spend the time?
If given a chance, in which public transport would you like to make out with me?
What is that one pick-up line that has always worked for you?

Deep Questions to Ask Your Boyfriend

As much as it is fun to ask romantic, sexually driven and fun questions to your boyfriend, some deep questions are also crucial in defining your relationship further. Many of these questions will also offer you a glimpse of his thought process and perspective on this relationship, without sounding like a serious proposal line. Take a look!

If we get married, where would you see us in the next 5 years?
How do you define love from your perspective?
In our relationship, what is the binding factor that will make it last forever?
If ever we reach a point where we find ourselves drifting apart from each other, what will you do?
Do you believe in the concept of together forever?
What is your fondest and most troubled childhood memory?
Are you currently happy in life? How would you like to make it better?
Would you rather stay in a dying relationship and make it work, or mutually end it and walk away?
How did you deal with your last breakup?
What was the takeaway from your previous relationship(s)?
What do your parents have to say about love marriage?
What is an absolute deal breaker for you in a relationship?
If someone lies to you that I am being unfaithful, what will you do?
If I want this and you want that, how will we conclude?
What changes or upgrades do you think we should make in our relationship to make it stronger?
What’s that one thing you’d like me to give up from my nature for good?

Questions to Ask Your Boyfriend to Test His Love

Test the waters and his love for you with these subtle questions that won’t be too pressurising and will let him express his affection for you freely.

Will you see me in my PJs, eating junk, and just being lazy, will you still find me attractive?
Would you like to have kids with me someday?
Will you still love me if I put on a lot of weight?
Will you still love me if you have to go against your parents’ wishes?
How would you like to propose to me someday?
If I tell you to elope with me and get married, will you?
If I am not feeling well, how will you take care of me?
If you don’t like something that I wear, but I love it, how will we settle the situation?
What would our life be like when we are in our 80s?
How will you officially announce our relationship on social media someday?
If I tell you that I am going out with my male friend for a cup of coffee, how will you react?
If I am not reachable for a few hours, what will you do? Will you be angry or worried?
What do you think about celebrating relationship anniversaries and special days?

Truth Questions to Ask Your Boyfriend

Some truth or dare questions are a hard pill to swallow, but equally essential to ask when getting into a relationship with someone. But the key is to ask them mindfully. Here’s how you can ask them!

What part of your nature would you like to change or give up completely?
Is there anything you’d like to change about me?
What is your biggest fear about our relationship?
When was the last time you cried?
Do you see us together 10 years from now?
What will your parents not be in favour of our relationship? How will you convince them?
What’s that one secret you’ve never shared with anyone ever?
How have you dealt with breakups in the past?
Are you happy in our relationship? Do you ever get doubts?
Would you still chase me if I said it is over and move away from you?

Fun Questions to Ask Your Boyfriend

Not every question has to be about romance, life or about him expressing himself. Here’s a list of light-hearted fun questions that you can ask your boyfriend while you are just goofing around!

If you had to choose between me and giving up on your most favourite food in the world, what would you choose?
What cartoon character would you say describes you best?
After marriage, if you find out that I snore while sleeping, how will you deal with the situation?
How will we survive as a married couple if I don’t know how to cook at all?
If you are given a choice to pick a female celebrity over me as my replacement, whom would you pick and why?
What would you not want to get caught doing in bed?
If you had to give me a secret craziest name, what would it be?
What if I burp in your mouth while we have our lips locked? How will you react?
If the bedroom is occupied and we want a quickie, where would you take me for it?
If I wake you up at 3 in the morning and tell you that I am feeling hungry, what will you cook for me?

Juicy Questions to Ask Your Boyfriend

Indulge in a round of sauce Q&A, asking these questions to your boyfriend and feel the gap between you two fading away instantly. These Qs are also a great way to let him know what you’d like him to do for you.

Me wearing only heels or me barefoot (and no clothes) while we are getting freaky together?
Which part of your body, if I touch it with my fingertips, will instantly turn you on?
Have you ever masturbated thinking about me or a celebrity?
If I whisper Pizza in your left ear and ‘eat me up’ in the right ear, which ear will you listen to?
What will make you instantly shut your work laptop down and give me 100% attention?
How will our first night after marriage be like?
Send me the juiciest good morning text right now.
If you have to bring any of our sexting sessions to reality, which one will it be?
Tell me the last dream you had about me?
What is your favourite part of our make-out sessions?

While these questions will surely help you have an amazing Q&A session with your boyfriend, it is also essential that you ask these questions at the right time. While being romantic, avoid asking serious questions like the future of this relationship. And when considering asking your boo some sexy questions, test the waters with mild questions and see how comfy he is answering them first.

And of course, maybe create an ambience that will suit the kind of questions you plan on asking. Lo-fi music, dim lights, scented candles and a drink in hand for a round of naughty questions? Between the sheets action, upcoming!

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