50 Things To Talk About With Your Boyfriend And Know Him Better

Love and Romance | |
Things to Talk About With Your Boyfriend
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You might be thinking of what things to talk about with your boyfriend to know him better? Funny, romantic, intimate, flirtatious – there are actually a host of things to talk about to know your guy a bit more.

It is said that you might be living with a person for a lifetime but still you might not know a few things about him. There’s no denying the fact that a relationship is an endless journey of discovery.

But once in a relationship you would want to know your partner more. His preferences, quirks and things that make him happy. Don’t worry we are here to guide you.

There are romantic things to talk about with your boyfriend that will not only be cute, flirty and fun but will also make the two of you feel more intimate. And of course, you will get to know him better.

Related Reading: 100 Romantic Questions To Ask Your Girlfriend And Make Her Heart Melt

50 Things To Talk About With Your Boyfriend And Know Him Better

Table of Contents

If you are newly dating we believe the conversations should flow effortlessly. That’s the only way romance will bloom and you will feel close to each other.

There are romantic things to talk about with your boyfriend and we list 50 of them. Armed with these discussion points your knowledge about your man is soon going to become deeper.

Romantic things to talk about with your boyfriend:

1. How romantic do you feel with me?

He could tell you he absolutely believes in getting you roses every other day, going for candle light dinners could be his thing, he could take you to that spot on the top of the mountains from where you can see the city lights and romance to him could mean a walk under the stars holding your hand.

He is hopelessly romantic, if he’s told you all this but he is definitely cutely romantic if he he wants to cook for you. And he is not romantic at all if he’s still groping for an answer.

2. Does the idea of a road trip with me excite you?

Just when you feel you have talked about everything you will surprised what travel can unravel for you.

If he wants to explore the world and is a traveler at heart he would instantly rattle off 10 romantic places he would want to take you to on a road trip and start off your travel plans. Aww! That’s so cutely romantic.

3. The most unromantic thing that you have ever done?

This would allow you ample reason to laugh. He could tell you that that on a high school date he dropped off his girl at the door not realizing she had closed her eyes for a kiss.

This could end up to be one of the cutest things to discuss with your guy. Don’t expect him to be totally truthful but things can get surely funny when you talk about the most unromantic encounters.

Related Reading: 30 Most Romantic Marriage Proposal Ideas

things to talk about with your boyfriend
What’s the most unromantic thing you have done?

4. Who is your celeb dream date?

If Charlize Theron is his choice then you know he loves the powerful woman with a lot of oomph. He could go for Scarlett Johansson or Jennifer Lawrence as well. Beauty and brains that’s what he digs then.

But if it’s author Margaret Atwood for him then you know it’s an intellectual conversation he is looking for. This is a great way to know him better.

5. What do you prefer to see – sunsets or sunrises?

If you are newly dating and want to know your boyfriend better then this question is perfect. You will get to know if he is game for waking up at dawn for a romantic walk on the beach or watching the sun go down in the mountains is his thing.

6. Marooned on a deserted island with me…

Questions to ask him
You get to know his idea of romance

He could just say that he would expect his girlfriend to carry the sexiest bikini. For the rest, you would know if he has read Robinson Crusoe or not. If he wants to be rescued quickly then you know languishing on an island is not his idea of perfect romance.

But he wants to stay on and tells you all the flirty, intimate fun he wants to have with you then you got yourself your own Knight And Day.

7. We are staying at a log cabin by a picturesque lake…

This is a fun thing to talk about with your boyfriend. He could say that he would look at the lake through the glass window and stay inside the quilts on a comfy bed making out all day.

Or he could talk about barbeques and swims in a picturesque setting. Outdoor or indoors? You already know him better.

8. The most romantic surprise you would want to give me?

It could be a ring from Tiffany’s or a yellow rose bush in full bloom in his garden. It could be an expensive phone or a picnic atop his car bonnet with the best views of the city.

In short, when you talk about these things with your boyfriend you know how romance works for him.

9. What’s the best thing about our relationship?

He could say, “I can be myself around you.” That’s the best compliment you could actually get but it could be your care, concern, your independent streak or just your simplicity that he dotes on.

An unpretentious relationship, that’s what he could go for as well. Talking about these things with him will make you feel intimate, romantic and happy.

Related Reading: 5 Ways Being Honest With Yourself Will Help You Understand Your Relationship Better

10. What’s your romantic expectation from me?

“Pamper me.” That’s what most guys would say. But guys usually love the small things. You cooking his favourite meal or making his cuppa in the morning or just dressing up for him. Their romantic expectations are simple.

If he is the adventurous kinds he could throw in the pole dance to make things a bit more interesting.

Serious things to talk about with your boyfriend

11. How do you look at yourself 10 years from now?

When you are in love you could feel that you have talked about everything but this question could actually get you where you never ventured. You will get to know how sorted he is in his head about his future.

If he is mulling over this question then he isn’t much of a futuristic person that’s for sure.

12. Are you happy with your job?

ask him serious questions
Some serious questions will help you know him better

Sometimes guys loathe their jobs but they wouldn’t talk about that in public unless it’s with the best friend. If he says he is happy about his job you are happy too, if he shares his troubles with you can dish out some handy advice.

These are indeed serious things to talk about with your boyfriend to know them better.

13. How grounded are you about finances?

When you are in love you sometimes feel edgy about bringing up personal finances but trust us this is a great way to know a guy better.

If he tells you he spends what he earns then you know he is an in-the-moment guy and he talks about savings and investments then you know future security is what he is working on.

14. Do you believe in living together or marriage is your thing?

This is a serious question you should ask your guy. Because this will help you understand if he expects you to move in with him or he plans to go down on his knees with a ring when he feels the time is right.

Either ways you will know how serious he is about his relationship with you.

Related Reading: Moving In Together Checklist – Know Your Readiness

15. How attached are you to your family?

If you love someone you should find out how attached he is to his family. His relations with his parents would actually have the keys to your own relationship.

If his parents were toxic then he could have insecurity and trust issues with you, if they had given him a secure and loving childhood then he would be your warm sanctuary.

16. You believe in a best pal or a host of great friends?

Does he have a best friend?
Is he an extrovert or an introvert?

Some men are the boisterous kind who love to party hard and move around with a gang of friends. Some men are shy and introverted and are happy playing golf with the best pal on Sunday mornings.

This is a serious but fun thing to talk about to know your guy better.

17. Do you keep in touch with your ex?

This is a delicate question but an important one to know your boyfriend better. If he says he does then you would know how he looks at his breakup and if he says he always follows the no contact rule then you can probe his reasons.

Past relationships can make or break the present one, so find out how much he is still into his ex.

18. Privacy or Social Media?

This one will totally reveal the person he is. Some people put every small detail about their life on SM but some can do the balancing act between privacy and exposure.

How he does it will tell you the person he is and how he would be dealing with your couple snaps.

Related Reading: Instead Of Making These Social Media Mistakes As A Couple, Do This…

19. Stick to the plans or you go with the flow?

Some people plan their life to the tee and get upset when things don’t go according to plan. Some are flexible and go with the opportunities and situations.

His answer will tell you how he looks at life and how resilient he is.

20. A dream you have for the future…

It could be setting up his own farm, changing his profession, writing that book or living near the beach. How do you figure in his future dreams? Do you see yourself sharing his dream?

These are serious things to talk about with your boyfriend that could give you peek into your future.

Things to talk about with your boyfriend when meeting for coffee

21. What’s the kind of coffee you prefer to drink?

What’s the kind of coffee you prefer to drink?
How does he like his coffee?

Did you know coffee reveals a lot about how a person is? Some love the latte and some go for the cappuccino. Some don’t mind experimenting with the hazelnut syrup while some can’t imagine coffee beyond the black shot.

Some opt for Darjeeling tea at a coffee shop too. What’s his potion?

22. Do you like exploring new coffee shops?

A coffee shop is a great place to unravel your boyfriend’s personality. If coffee for him is that brown large cuppa of Starbucks in the morning and nothing beyond that, then you know he can’t experiment with his brew.

But if he is game about checking out new places you can instantly suggest one and have a great time together.

23. Your favourite coffee shop?

If he answers Starbucks he’s with the half the world’s population, but if he talks about that quaint joint that brews homemade coffee and has a corner table in an open-air courtyard, then you know he is experimental.

It tells you he’s cutely romantic too. Picture him in a set up like this and you will know.

24. Is it a great place to check out girls?

Chances are he would look this way and that way when you throw him this question but after that if he tells you he never checks out any girls then maybe he is not being honest or you scare him to death.

Or he could just laugh and say, “Yes.”

25. Are you into books?

If you both find a connection over books then this could become your talking point for life. Don’t be surprised if he starts telling you the plot of a thriller he’s read recently.

If he isn’t into books then you missed out a great opportunity of endless conversations. No issues talk about life. He will surely have plenty to tell.

Related Reading: 20 Questions To Ask Your Partner To Build Emotional Intimacy

26. What movies do you like to watch?

movies do you like to watch?
Watching movies together is a great way to relax

If not books, films are something everyone watches. He could be a film buff then that’s great for you. But if he catches a show on a rare Saturday night then also you get to know what films work for him.

What’s the kind of film he likes? If Jim Carrey is his man then you have a funny guy there and if he watches Avengers on the loop you have some fantasy to keep up with.

27. Is it the multiplex for you or Netflix?

Despite having a 60-inch screen at home some people love the multiplex experience. Some people would take the pains to book the tickets, drive down to the theatre and devour a movie with popcorn.

Some love the feel of the couch and a movie on Netflix. Microwave popcorn works great for them.

28. Who’s your favourite hero?

This would tell you if he hearts the macho Hollywood hero or is into the nuances of acting. If he likes X-Men star Hugh Jackman you know it’s all brawn for him and if he keeps talking about Robert De Niro then you know what a hero means to him.

29. Is cooking your thing or ordering in?

Some men love to cook and can teach you a thing or two in the kitchen. Some men just order in what they want. Some survive on salads and beer.

This is one of the things to talk about with your boyfriend that will reveal a very important character trait. It’s a great conversation to have over coffee.

Related Reading: 6 Signs You Have A Foodie Partner…And You Are Loving It!

30. Your favourite cuisine….

He could scratch his head and then say a burger. Or he could say Japanese satay and Korean sesame fish. It’s  a great way to know how much he is into food.

You get to know if food would be a romantic link between the two of you.

Flirty and funny things to talk about with your boyfriend

31. What did you think of me when we first met?

ask him funny questions
The funny questions are great for a good laugh together

This is a tricky question and be ready to deal with his honest answer. He could just tell you he thought you were a dumb blonde in a frumpy skirt. Or he could say he thought you were the hottest thing walking the earth.

32. Your funniest childhood memory…

It could be something from Halloween, a prank played on a neighbor or the neighbor’s dog rescuing him from the pool thinking he was drowning when he was actually practicing holding his breath under water.

Funny childhood memories can give you a glimpse into his childhood.

33. The most adventurous thing you have ever done?

He could say jumping over the neighboour’s fence or bungee jumping. You get to know how adventurous he is from this question. He could even tell you that he’s hitch hiked with a rucksack and gone around the globe.

Related ReadingRs 9000 for Bottled Water? No Way! Travel on a Budget

34. What’s it about me that you feel attracted to?

Another tricky question this one. He could tell you it was your eyes, or the curly brown hair or your sense of humour or your ability to have intelligent conversations.

He could talk about your well-rounded breasts in bed but definitely he wouldn’t choose the coffee shop.

35. Cuddles or kisses?

Some guys love to cuddle, spoon and just lay in bed holding you for hours. That’s their way of expressing love. Some want the hot deep kisses followed by action.

Check out how he feels about you when you ask this flirty question.

36. On a special date I should wear a red gown or denim shorts?

Thing to talk about to know him better
He could prefer you in a red gown

If Lady In Red is his song then he would go with a red gown. If he loves your casual look then shorts or denims are what he would love you in. He could go for both. You never know.

37. You like make-up on women or the natural look?

How he likes his lady to look is what you get to know from his answer. Or he could just leave it to you saying, “I love you any which way!” We can see the natural blush already.

You already know him bettter.

38. The most embarrassing moment in your life…

All of us have had that. He would have one too. It’s a funny and intimate question that would give you an opportunity to laugh and you get to know what kind of a funny guy you have in your life.

Related Reading: 7 couples confess how they got caught while making out

39. What cartoon character can I be?

Minnie Mouse could be his instant answer. But if he’s into cartoon films then he could tell you Ariel, Anna, Dory and the likes. You better know our characters well. If he talks about super villain Gru… then ah well!

40. Something you would want as a gift?

something you would want as a gift
What’s his idea of a great surprise?

Your hand could be his answer. Or the latest Bugatti Veyron or a baby with you. A great way to know what’s the kind of gift he would cherish will be to ask this question.

Intimate things to talk about with your boyfriend over text

41. What turns you on?

An honest answer would be big breasts. But he could tell you it’s your perfume or the way you look at him through your sunglasses.

42. Is there anything you go crazy about?

Beer or car racing games? Football or baseball? Five-bedroom villa at Beverly Hills. Chances are you won’t figure in this answer. But on second thoughts he might just add sizzling sex with you.

43. What is your sexual fantasy?

Doing it in the car or doing under water or doing tied up to the bed. He could have one or a host of them. Depends on what he chooses to tell you. This is a fave question for most men but if he is acting disinterested then he just being shy.

Related Reading: How To Have A Sex Chat With Your Man For The First Time

44. How do you feel about making out in the shower?

What's his sexual fantasy
Most men love to make out in the shower

Yes, yes, yes!! We can already see him uttering that. But if he tells you he would rather only do it in the bed he isn’t being adventurous. Then maybe it’s time to initiate him in the bathtub.

45. What’s your take on BDSM?

He could be cautious to answer this. But if you are in love you don’t shy away from adventure. He will tell you what he feels about BDSM. The truth will help you understand him better.

46. What’s the position you like most?

That’s another intimate question he would love to answer. Doggie is an all-time men’s favoutie but Cow Girl and 69 are also things they love to try. He could tell you about a sex position that he would want to try with you.

47. Do you like to play with toys in bed?

Boys like toys but when it’s in bed they like to use it more when they are with their girl. Talking about sex toys will tell you what works for both of you.

Related Reading: What men want from women

48. What’s your favourite part of my body?

know him better
Sexting is a great way to know him better

Umm…he doesn’t need to think but he is thinking whether to tell you the truth or not. If he says it’s your eyes he is lying blatantly. Prod him a bit more then.

49. Where do you love to be touched?

We believe it’s only one place that men like to be touched but they have a sensitive body too and love some touch in their erogenous zones. From nipples to the neck, from the ears to the torso he could take his pick.

50. Do you like lacy lingerie?

Most men love sexy lingerie. But some like it smart and some like it lacy and feminine. What’s his choice? He might even want to go lingerie shopping with you or for you.

With these 50 questions you have plenty of things to talk about with your boyfriend – ranging from serious, cute to funny and flirty the answers would bring you closer. After you have a conversation around these questions you will surely know him better.


1. How do you make a conversation interesting with your boyfriend?

There are a host of questions you can ask your boyfriend that are great conversation starters. To make a conversation interesting keep things humorous but talk about romantic, intimate and serious things as well.

2. What to to talk about with a guy?

Having common interests helps in great conversations but you can always ask interesting questions to know a guy better. Talk about his childhood, his interests, his future plans, his idea of romance and fun.

3. What are good questions to ask your boyfriend?

If your questions are funny, romantic, intimate, tricky, serious then these are good questions to ask your boyfriend. You can ask some flirty questions on text also.

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