The Very Best 50 Questions to Ask Your Boyfriend

The Very Best 50 Questions to Ask Your Boyfriend

Do you have that special someone in your life that you want to connect with on a deeper level? When we find love, the energy hits us like a full force field! However, can those physical feelings reach us on an even deeper level. It seems like sometimes those serious talks are little too distant, so how do you go about instigating intimate connection that will stand the test of time?!

We’ve got the ultimate solution set up in this set of ‘50 Intimate Questions to Ask Your Boyfriend So You Fall Deeper in Love,’ which we’ve sub-categorized under ten helpful sub-headings to bring you closer together…



Questions to ask your boyfriend
We all want to know what it is that makes us special to the man of our dreams!… What was it that made them fall in love with us and not another? Why is it our eyes that make their pupils dilate? Maybe, they’d like to share it with you… next time you see his eyes go super wide ask him one of these five questions and feel yourself falling deeper in love as he shares his favorite features about you. You can’t deny you love some praise now and reassurance now and again!


1. “What is it that you love about me the most?”

Maybe it’s your eyes, your lips or your huggable thighs, or even the way you roll your eyes and laughs in your own unique way… Go on ask him what it is about you that really makes his cheeks shine.


2. “If you could change anything about me what would it be?”

We’re not always perfect!… Is there a feature or characteristic you could work on that annoys or offends him?  We all have our good and bad points and talking about them is proven to bring you closer together.


3. “What color do you think suits me best?”

A man who can’t dress a woman is a myth!!.. Most are excellent fashion critiques they’ll cut to the chase and tell you what goes and what doesn’t. Ask him what color he thinks suits you best and dress in it to satisfy his opinion.


4. “How’s my hair looking today?”

We all have a bad hair day now and again!… I sometimes question the theory and wonder if we’re really having an insecure day we like to take out on our hair. If your feeling like this… ask your man for some reassurance, what he thinks about your hairstyle.


5. “Do you prefer me with makeup or looking natural?”

An age-old question with an answer that usually leans to 95% of men saying they prefer us ‘natural!’ So give the makeover a rest for today and listen to him, you will feel more secure knowing he will love it!



You could never forget that magical moment you first met!!.. When he had you on the tip of your toes… and the same for him. Try rekindling some of those precious ‘first time’ memories and discuss how you’ve grown together.


6. “Do you remember how we first met?”

Sharing your different perspectives on how you first met will offer an interesting comparison to the special time when you came into each other’s worlds.


7. “How did you get me to fall for you?”

Let him confide in you those old tricks he had under his sleeve in the first stages of your love.. that could answer a few uncertainties surrounding those shy first dates you had together.


8. “Did you imagine then… we would be where we are today?”

Did he always have you in mind from the very start… or was it just a casual fling to begin with? Don’t get offended if he answers with a ‘no,’ or hesitates, so he wasn’t head over heels with you at the start, but he certainly fell headfirst… when he got to know the real you!


9. “When did you realize I was the one for you?”

Get him to share that glorious moment when he first saw you in a ray of light! It’s healthy to talk about when you first fell in love because it reassures you of the positive journey you have taken so far together.


10. “Was is it love at first sight for you?”

When you came into one another’s worlds… It could have been him or you that looked up first,  there’s no denying there was an instant connection! Find out how he felt in that first decisive moment.

Next: 50 Questions to Ask A Guy



Questions to Ask Your Boyfriend

11. “What is it that makes us work the most do you think?”

What makes your love stand the test of time?… Ask him what he thinks sets you apart from the rest it and share your opinions on the beauty of what your love has become.


12. “Do you think we could improve on our love?… If so what do you think it would be?”

There could be nothing you need to improve on, but it’s hard to believe because nothing’s ever perfect! However, you can work on making it close to perfect and the best way to start is by talking things over.


13. “If there’s one thing you could do for me, or I could do for you what would it be?”

Compromise will get you both a long way! Suggest things you can do for one and another and take time and pleasure in seeing to each other’s needs.


14. “On a scale of 1 to 10, how much do you love me?”

There’s no real way of measuring your love for each other, but if you could rate it on a scale of 1 to 10… what would it be?


15. “What make’s our love different to all the rest?”

There’s something that seems to set the world on fire every time you are both together… discuss what it is that sets your love different from the rest. Lavish in the beauty, which your love ignites and talk freely about it!



You spend every day together, so you’d think you’d know each other well, but it’s not always the case! Most couples find it hard talking over deep feelings with their partners because theyare afraid to ask them, or unsure how to ask, in case they say something out of turn. If you’re unsure where to start getting intimate on a quizzical point of view then start with something easy-going like: how well do you know each other?… It may lead you much deeper!


16. “What’s your ideal date?”

Is it always you suggesting where to go on a date?.. It’s okay it comes natural to us to plan and find ways to revamp our love life. Still, it’s okay if you want to suggest he decides where to go on your next date because you might be pleasantly surprised!


17. “What’s my favourite romantic spot for us?”

How well does he know you both and will he be in tune to your favourite spots that remind you of each other. Make it extra special and get him to take you there on your next day out and rekindle some soft memories.


18. “If could go anywhere.. where would it be?”

We all have a dream place we would like to go! You should share them with each other and then make those dreams real and plan to visit them together in the future. This is an excellent therapeutic tool to rekindle your love and talk about your deepest desires and make them come true as a unity.


19. “What’s your favourite food?”

Do they have a favourite comfort food you don’t know about?… Don’t forget the ‘The way to a man’s heart is his stomach.!’ So when you find out his favourite meal get those cooking gloves on and cook him up a feast.


20. “Do I like milk in my tea/coffee?”

This is a figure of speech, as it should be an easy question for them to answer. How well does he know you? How often does he make you that delightful cup of tea, or coffee.. in the morning, or getting in from work…

Next: 50 Interesting Most Likely To Questions



Questions to Ask Your Boyfriend

“Actions speak louder than words…” Find ways to turn your deep discussions into moments you can actively share together. Only this way can you fully move forward and experience what it is to be in love with each other. First you talk, then you act and make memories together. Here are some ideas of things you can ask your man and suggest to do together:


21. “Where do you want to take me for dinner this weekend?”

It’s been a long week of routine and you’re too tired to go deep, well why not suggest going out for food at the weekend. You don’t have to push the boat out… go local, cheap and still make great conversation, whilst together you can unwind away from home.


22. “Shall we try doing something new?”

This is quite an open question, which is sometimes cool because you can let them interpret it however they like. The main objective here is that you’re leading them on to trying something new, which is great therapy to reigniting passion back into your relationship.


23. “Shall we start a hobby together?”

This is a great way to find an interest that you both share and spend quality time together  enacting that leisure that you both enjoy. It will most definitely bring you closer and breaks your weekly routine in a positive, recreational and bonding way.


24. “Let’s meet for a drink after work?”

We all need to unwind with a light drink after a stressful day, but instead of ditching him to go out with your work friends, which probably upsets him.. Invite him out too!  Meet him in a new cocktail bar downtown and take the edge of life by pretending like it’s a weekend.


25. “Shall we watch a movie?”

It’s time to zone off together and cuddle up on the sofa together watching a movie. You most likely have different tastes in film preference, but meet in the middle and find one you will both enjoy!



The moments when we get physical and experimental, which I’ve titled –  ‘in the bedroom,’  really could be anywhere at any time… when you’re in love you can’t help to show it physically with each other! It is the ultimate pleasure that keeps him coming back for more. Don’t be afraid to ask questions about it to get you both in the mood… and suggest something new!


26.”What’s your ultimate bedroom fantasy?”

Every man has a bedroom fantasy. Let him share it with you and if it’s appropriate to your own desires too, then make his wish come true. It will set you both on fire knowing that you’re in control of his ultimate sexual desires.


27. “What’s your favourite form of sexual pleasure?”

All men have an instant switch on the button that brings them to an ultra-fast climax. Find out what it is, if you don’t know already and set his world on fire!


28. “Is there a feature about me that turns you on straight away?”

There is definitely that one feature about you that instantly makes him want to undress you! wouldn’t it be interesting to know what it is?…


29. “Do you like it when I kiss you there?”

Experiment with places to tickle his senses with your lips that doesn’t involve his! Find his sensitive pressure points and tempt him a little. Ask him if he likes it and you’re sure to get a positive reaction.


30. “Am I wearing any underwear?”

It is an open question, but in your mind, you already know the answer is no. You can still initiate this thought and get the ball rolling with this ultra sexy – ‘get him straight to the bed’ – line.

Next: 60+ Relationship Would You Rather Questions



Questions to Ask Your Boyfriend

We always want to reassure of the future, yet men can shy away from talking about their future sometimes. They’re easy-going and don’t like overthinking deep matters and prefer to live in the present. So when you want to approach the subject of your future together be gentle and find the right time. Ask him these five questions and ease them in at the ideal moment, then wait patiently for him to respond, whilst showing affection for reassurance. The blunter you are, the quicker they will react and uncover they’re feeling without time to react.

So go on ask him what he truly feels about the future..


31. “Where shall we go on our next holiday together?”

Holidays are a perfect disconnection for you both to enjoy quality time away from work, home, friends and the general routine of everyday life. You can explore the sights, whilst discovering each other in a completely new light… letting down your guards!


32. “Do you see yourself spending the rest of your life with me?”

The ultimate question that reveals what he really thinks if your future together. Don’t forget this is a big question you’re asking him!… So don’t get upset if he hesitates or answers “I’m not sure.” If this answer persists, only then you can begin to question your future together.


33. “What’s one thing we could change about each other that could help us move forward and understand each other better?”

You may find an invisible barrier appear between you now and again, which blocks you from understanding one another. A character clash or a failure to understand each other’s thoughts or beliefs could then lead to an argument. Share these little pet hates with him and try and adapt to each other’s flaws.


34.“Do you want to start a family together one day?”

You’re not getting any younger and you’re completely head over heels in love. Why wouldn’t you want to spend the rest of your lives together?… because he hasn’t asked you yet! If it’s bothering you that much, just bite the bullet and ask him. Turn that dream into a reality and casually approach the question with ‘one day’…  it gently leads him into the idea.


35. “What would you like to accomplish from life?”

Your goals and future are important, but so is theirs. Show that you care about them by having a good healthy chat about where he finds himself at the moment.. in his career, with friends and family, his own mental and physical well-being, or even with you! He will appreciate the opportunity to open up and have someone listen to him… give him guidance if he needs it!



Sometimes even the most simple questions you ask on a day to day basis can insight you into their deepest feelings. Especially, if you look at the greater picture. Without looking too deep into things…  ask him one of these great silence breakers to get the conversation running, especially if you see him quiet and concerned about something:


36. “How are you feeling?”

It’s a short, simple question that shows you care about them and what’s going through their mind. If they are feeling great they will be happy to share it with you, if they are not they may want to talk about it…


37. “How was work today?”

After a hard day at work, you’re dying to get home and see his familiar face to get some normality back. He probably feels the same, so kick start your evening off by asking him how his day was at work… he may need to off-load!.


38. “What shall we have for dinner?”

It’s that moment in the day where you can let go and enjoy a meal in the beautiful company of your beloved boyfriend. Life can get monotonous, so spice things up a bit and suggest a candlelit dinner to take the pressure off life… enjoy your time together!


39.“Do you want me to put some music on?”

Music is the perfect vibe-setter! If you’re both feeling low, or there’s a little awkward silence… stick a soundtrack on that, you both love! You’re sure to re-connect in tune with one another’s rhythm.


40.“Do you want to read the newspaper headlines out to me?”

On a glorious weekend, morning sat at the kitchen table eating breakfast and his nose is in the newspaper. If you’re feeling disconnected from him, then get him to read out the headlines discuss together about putting the world to rights!

Next: 70 Questions to Ask Your Crush



Questions to Ask Your Boyfriend

That’s enough about us, let’s talk about them for a while! We can’t deny that we like to own the conversation at times. Men are easy-going and go along with any chat, but they also need to open up. Encourage him to talk about his thoughts, his past and what could be ticking away in his mind that he might need some release from…


41. “Would you prefer to read or watch a movie?”

Maybe, he doesn’t always want to talk and simply wants to disconnect from everything. Find out his secret remedy! Is he a book person, or would he rather put on an action movie and get lost in its fictional plot?…


42. “If you could start a hobby what would it be?”

They all need a distraction and it doesn’t always mean spending time with us, however unfathomable… yes sometimes they need some time away from us! Suggest he takes on a  hobby doing something he’s passionate about to get some active, self-empowerment.


43. “What are you most afraid of happening to us?”

How has he been acting around you lately?… It’s natural for us to have moments of insecurity in our relationships, maybe the stress has got on top of you both and you’re not communicating like you usually would. If you feel he’s been shut off with you recently, or you yourself have some feelings of insecurity confront them together.


44. “What have your other relationships taught you before now?”

It’s hard to think that your boyfriend has had a whole life before you came into it, including other girlfriends. Remember, they are his past and you are his present… if anything they will have taught him valuable lessons in love!


45. “Have you loved another more than me before?”

Then again, there could always be that god awful thought that someone left a scar so deep that she never actually left him… We hope not! However, if you’re feeling insecure about it, maybe you should ask him.



Then to round this set of 50 intimate questions to bring you and your partner closer together... There’s only one way to really win his affection over and bring him undoubtedly closer to you and that is to ask him questions, which will please him. Make him feel like there is no one else the matter to you but him.


46. “Would you like me to give you a massage?”

Maybe he’s looking a little tense, or you just want to get your hands all over him with hot, stimulating essential oils. Offer him an all-over body massage and connect with his mind and body as he relaxes to your touch.


47. “Would you like me to make your lunch for work tomorrow?”

It’s a fact that men like to be looked after! They love you making effortless gestures to take care of them on a day to day basis. They will get comfort opening their lunch boxes up to find the delightful snack you’ve prepared them to get them through those hours of earned hard labor!


48. “Can I get you a drink?”

Make an effort to apprehend his needs and make him feel like he really couldn’t live without you. If he’s sat relaxed on the couch watching sports ask him if he wants a drink and keep him happy.


49. “Would you like me to wear your favourite dress?”

You think your boyfriend doesn’t know your wardrobe, but you’ll be pleasantly surprised.. he’s sure to have a favorite dress that you wear that sets his heart on fire! Find out what it then surprises him by wearing it and connect with him completely.


50. “Would you like me to press your shirts for you?”

A shirt pressing is not in their list of favorite things to do and they will leave it till the last minute if they have to!! Take your time to do little chores for him and ask if he wants his shirts pressed.


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