1. What was your first impression of me?
On a date night and can’t think of what to talk about next? Such curious questions to ask your boyfriend can take you on a trip down memory lane.
2. Did you think our relationship would last when we first started dating?
Want some freaky questions to ask your boyfriend? Make sure you add this one the list and watch your guy squirm with uncertainty at how to respond to this one.
3. What is your best memory from childhood days?
If you’re still in the initial days of dating and getting to know each other better, ask him this to get some insight into what growing up was like for your man. After all, our childhood experiences do have an impact on our adult personalities.
4. How well do you get along with your siblings?
This the perfect follow-up to family-related questions to ask your boyfriend. Also, immensely essential, if you’re both thinking long-term. Knowing the kind of bond he shares with his siblings and family will help you prepare yourself for the kind of interactions you can expect to have with them in the future.
5. What was your favorite TV show as a child?
While you’re on the subject of his childhood days, ask him about his pop-culture preferences. This may sound like one of the more casual questions to ask your boyfriend but if you’re both more or less the same age, it can give you a new territory to bond over.
Related Reading: What to do after a fight with your boyfriend?
6. Do you prefer cats or dogs?
This is yet another essential question to ask your boyfriend in the getting to know each other phase. The cats or dogs or no pets at all preferences can often prove to be deal relationship deal breakers, especially if one of you is an ardent animal lover.
7. What is the one thing you can’t stand about your current place of work?
This is one of the questions to ask a guy you like. Job satisfaction and a sense of professional fulfilment are vital for a person’s peace of mind. If your boyfriend is struggling on that front, it could impact your relationship too.
8. And the one thing you appreciate the most?
If he has laid his heart bare on everything unbearable about his workplace, follow it up with this question to get a complete sense of how he views his professional life on a whole.
9. How do you unwind at the end of a long day?
Once again if you’re thinking long-term and want to end up living together at some point, it’s important to know what his wind-down routine is like.
If you like to curl up with a book and he prefers to blast the music, it can be a recipe for disaster.
10. What are your views on religion?
Not all partners have to be on the same page in terms of their religious beliefs. However, staunch beliefs and intolerance of divergent views on god and religion can often become a sore point between couples.
11. If you got a do-over, what would change about your life?
Asking question to boyfriend
This is one of those deep questions to ask your boyfriend that will give a clear insight about your man’s sense of achievements and regrets in life.
12. How would you describe your first crush?
If your last question made the vibe too intense, lighten up the mood with cute questions to ask your boyfriend such as this. The first crush is a pleasant memory for most people.
13. What’s your take on gay relationships?
Speaking of beliefs, it is vital to understand how liberal or conservative your partner. This is one of those questions that will spill the beans without fail.
Now, they don’t necessarily have to be a champion of LGBTQ rights but you have to sure you’re not with a homophobe either.
14. Have you ever considered an open relationship?
One of the tricky love questions to ask your boyfriend would be this one. This can seriously tell you where he stands. Intimate questions such as this can help you understand their take on romantic relationships.
15. What is the one pet name you’re embarrassed of?
The key here is to mix things up. What better way to do that than asking him about his embarrassing pet names. It gives you the perfect arsenal to playfully annoy your boyfriend.
16. What was your first sexual experience like?
Looking for intimate questions that will help bring you closer to your boyfriend? This is it. As long as he is comfortable talking about it, ask him for details about who, when, where, and most importantly, how it made him feel.
Related Reading: What Is Consent In Dating?
17. What turns you on?
This is certainly one of the fun questions to ask your boyfriend. Asking about the first sexual encounter gives you the perfect opening to bring some dirty questions to ask your boyfriend into play. Start with a basic one about his turn-ons.
18. Is something about me turning you on right now?
If you want to bring on some zesty energy, this is one of the questions to ask a guy you like. Then, you can turn the heat up by bringing him to the present. Even if he wasn’t turned out until now, this question ought to do the trick.
19. What, according to you, is the best way to resolve a fight?
Every couple has their share of disagreements and fights. That’s why this is definitely one of the relationship questions to ask your boyfriend.
20. Have you ever cheated in a relationship?
Another one of those freaky questions to ask your boyfriend that he’ll struggle to answer. But you know it has been on your mind, so just go ahead and ask away. These tricky love questions always bring out interesting responses.
21. What are your views on cheating/monogamy?
Depending on how he answered your last question, ask him his views on faithfulness in relationships. This is an interesting way to get to know a guy and understand ow and what he feels about dating and its facets.
22. How would you define love?
Yet another of those deep questions to ask your boyfriend that will help you understand your man a little better. It’s also a great way to assess if you’d be compatible in the long run.
23. Have you ever done drugs?
If you’re looking for freaky questions to ask your boyfriend, this one cannot be left out. Besides, it’s important to know if he’s tried drugs for the sake of experience or is a habitual user or someone who’s completely anti-drugs. Drug addiction can be detrimental to your relationship.
24. Do you have any addictions?
This is definitely not a question to ask on the first few dates, but if you start seeing each other officially, you have the right to know about your partner’s vices and addictions.
25. What is your idea of a romantic evening?
Now, this is one of the perfect romantic questions to ask your boyfriend right when you start dating. You’ll know what to expect from your date nights in the future and it’ll come in handy in planning those romantic surprises for him.
Related Reading: 10 Questions Every Girl Should Ask A Boy Before An Arranged Marriage
26. What would your dream romantic holiday look like?
As a couple, you’d be taking trips together. It is only natural to know what your boyfriend’s expectations from these vacations are. If you’re a mountain person and he loves the sea, you’d have to figure out an arrangement that offers the best of both worlds.
27. Are you an adventure enthusiast?
You have to know the answer to this question before you become too emotionally invested in your boyfriend. If he’s an adrenaline junkie and you’re not or vice-versa, co-existing can become a nightmare.
28. What’s your idea of sound financial planning?
This also becomes one of the vital relationship questions to ask your boyfriend, especially if you’re at the threshold of taking the next step.
29. Are you in debt?
Laying your cards on the table about your financial health is vital for the health of your relationship. If your partner is not forthcoming on that account, don’t hesitate to ask.
30. How do you deal with confrontation?
Is he the confront the uncomfortable kind of guy or someone who prefers to bottle up feelings? You have to find out, and that’s why this is one of the essential deep questions to ask your boyfriend.
31. Do you believe in destiny?
How to know your lover is all about asking him the right questions. It’s important to ask this question to make sense of his beliefs and value system in totality. They do not have to align completely with yours but this is necessary to understand him better.
32. What is the one thing about us that you absolutely love?
This one is a classic that never fails to do the trick. So, if you’re running out of romantic topics to talk with your boyfriend, ask him this. The answer will probably make you smile with glee!
33. What is the one thing you and I don’t have in common?
Sure, you have your own take on your commonalities and difference, but it’s always interesting to get a fresh perspective on things. Even more so when that perspective is your boyfriend’s.
34. What attracted you to me?
This is one of those cute questions to ask your boyfriend that also border on romantic. You probably already know the answer, but hey, it’s a whole other experience to hear it from the horse’s mouth.
35. When did you realize you were in love with me?
Realizing he was falling in love
Whether you’re celebrating an anniversary or just talking late into the night, this is one of those romantic questions to ask your boyfriend that will always hit the nail on the head. Your question will take him back to that moment in time when he first realized he was falling in love and those warm, fuzzy feelings will come gushing to the forefront.
36. Are you scared of commitment?
One of the quick fire questions to ask a man would be this one. This is something to talk about if you’ve been together long enough, settled in the relationship, but he hasn’t made any big gestures signaling a long-term commitment.
37. If you had a get of jail free card, what would you use it for?
Certainly one of the most fun questions to ask your boyfriend. Hypotheticals are a great way to get a sneak peek into a person’s deepest, darkest thoughts. You’ll learn things about him that you could not imagine learning otherwise. They often prove to be great conversation starters too.
38. How would describe an ideal wedding?
Inching toward the big day? Or just know you will walk down the aisle with this man waiting at the other end? Ask him what his idea of an ideal wedding is. Would he prefer an intimate ceremony or a big wedding? Does he like banquets or open arrangements?
Often weddings become too bride-centric while the groom becomes a sidekick.
Remember that it is the most important day of his life too, so factor in his preferences. And keep them in mind, if and when you plan the wedding.
39. What is your retirement plan for yourself?
When discussing life possibilities, take a no holds barred approach. It’ll give you an insight into what growing old with this man would look like. This question is not just important to know him, but also for you.
40. What is the one thing that I do for you that you cherish the most?
Circling back to romantic topics to talk with your boyfriend, ask him what he appreciates most among all things big and small that you do for him and your relationship.
41. What is my one habit you can’t stand?
This is certainly one of the unique questions to ask your boyfriend. Not all the questions have to be about him, use this as an opportunity for some healthy introspection as well.
42. If you could change one thing about us, what would it be?
This is one of those relationship questions ask your boyfriend that can help you figure out the problem areas and work on fixing them. Tread carefully and do not get paranoid at his honest answers.
43. And the one thing you absolutely love about us?
When he tells you what he doesn’t like about the relationship, it’s bound to sting a little. This is the perfect antidote to your previous question. It’ll prevent any negative emotions from spiraling out of control.
44. What is your best sexual memory of us?
Been having a bit of a dry spell? Such dirty questions to ask your boyfriend can totally steam things up between you two. How to know your lover lies in understanding what he likes. This question is important for you to know the same.
45. What is the one thing I do in bed that blow your mind?
If you’re feeling particularly naughty, ask him this. We promise one thing will lead to another.
46. Wh at is your best sexual memory with a partner other than me?
Feeling naughty and adventurous? Ask him about his sexual escapades from the past in detail. It will also give open up the possibility of more questions to ask your boyfriend about his ex.
47. Is there an ex you still think about?
With questions to ask your boyfriend about his ex, make sure you keep an open mind and don’t take offence. The idea here is to fortify your bond with your boyfriend and not create a reason for a rift.
After all, most of us have that one ex – the one that got away – that we tend to think about every now and again.
48. Have you kept any souvenirs from your past relationship?
A jacket, a letter, a perfume, an old t-shirt – so many people have relics from their past lingering around. Does your boyfriend have them too? Ask and you shall find out.
49. How have you dealt with heartbreak?
This is one of the intimate questions that will make you see his vulnerable side. Did he cry himself to sleep on many nights? Was there binge drinking and drunk calling involved? And most importantly, is he over her completely?
50. Do you cry easily?
Crying is a good sign
Men have been taught to toughen up and put up a tough exterior for centuries. If your boyfriend can cry, it means he has embraced his soft side and emotional vulnerabilities. That’s an amazing trait to have in your man.
51. What keeps you up at night?
Another one of those intimate questions that will help you understand your boyfriend on a deeper level, as you gain a sneak-peek into his fears and insecurities.
52. Who is your biggest support system?
We all have people in our lives we lean on in times of distress. To know your boyfriend fully well, you have to know what his inner circle looks like.
53. What is your spirit animal?
This is one of the more fun questions to ask your boyfriend casually. Quirky questions such as these always come in handy when you want to lighten up the vibe of the conversation.
54. What is the weirdest situation you have ever walked into?
Parents making out, a sibling caught in the act, someone undressing…we’ve all had our share of weird moments in our lives. Asking your man about his definitely qualifies as one of the funny questions to ask your boyfriend.
It’ll lead to some hilarious revelations.
55. What’s the grossest thing you’ve done?
One of the more unique questions to ask your boyfriend, this will incite some laughs. This question is equal parts funny and freaky. Be prepared to listen to some rather unpleasant details.
56. If you could be a vegetable, which one would you be?
Not everything you ask him has to be serious and deep. These funny questions to ask your boyfriend can really liven up the mood.
57. Who was your first celebrity crush?
Remember yours? Yes, exactly. First celebrity crushes are often embarrassing and hilarious.
58. What is the weirdest fashion trend you followed to a T?
Overalls, leather pants, weird hairdos, gel-laden hair…what was the one raging fashion trend from the past that your boyfriend embraced wholeheartedly and now wants to erase the memory of completely. There’s a good chance there is photographic evidence of this sojourns.
Find them and you’ll double over with laughter.
59. How would you react if a guy asked your number at a bar?
This is definitely one of the funny questions to ask your boyfriend that will lead to some equally funny responses. He may even have an anecdote or two to share.
60. What’s happening in this Instagram post?
Open his Instagram account and ask him about the story behind the most quirky or offbeat post you can find. But do not make it sound like you are always stalking him online.
61. What is the last item on your Google search history?
While you’re at it, ask him about his last Google search. We bet something interesting will come up and you will open up a range of things to talk about.
62. What’s your take on porn?
We have for you yet another freaky question to ask your boyfriend. Now that you’re romantically involved, you have the right to know these intimate details.
63. Would you expect me to watch it with you?
Depending on your take on the whole concept of pornography, this can either be a dirty question to ask your boyfriend or something that can trigger a full-blown debate. But ask you must to know what potentially awaits you in the future.
64. What are your thoughts on sharing household responsibilities?
Will you be the one running errands, doing chores while pursuing a career? Or is he on board with the idea of doing the dishes, taking out the trash, cooking an occasional meal or fixing breakfast every morning?
65. Which was the first dating app you signed up on?
Taste in dating apps
Is he a Tinder guy or does he prefer Bumble or OkCupid? His taste in dating apps can tell you a lot about his preferences.
66. What was the worse date you had via a dating app?
Dating apps and disastrous date experiences go hand in hand. Ask him about his. How to know your lover is all about knowing his histories and experiences. Ask him this question straight up!
67. Have you ever been attracted to a friend?
This question becomes particularly pertinent if there is a special female friend in his life that he is too close to. This is one of the questions to ask your boyfriend about his ex to understand his dating history better.
68. If you could pick a superpower, what would it be?
Haven’t we all entertained this question from time to time? So, ask what your boyfriend’s preferred superpower would be and compare notes. Together you can embark on a fantastical journey, imagining how you two would club your powers to save the world.
69. What do you imagine you’d win a big award for?
Would it be the Nobel or the Pulitzer or an Academy Award? Or is he a Grammy’s kind of guy? It is one of the fun questions to ask your boyfriend that will give you a sense of his secret aspirations and dreams.
Related Reading: Is Your Jealous Boyfriend Being Possessive And Controlling?
70. Have you ever drunk texted a wrong number?
A classic funny question to ask your boyfriend. Did he ever send a text bitching about his boss to the boss? Or a message that was meant for his ex to his mom?
71. What’s the one food that everyone loves but you can’t stand?
Does he think pancakes are overrated? Or does he hate Nutella? Time to challenge some popular opinions. May be follow up with some of your own, and brace yourself for some passionate arguments.
72. What the one conspiracy you believe in?
Does he believe the moon landing was a farce or that the CIA was behind JFK’s assassination? This question can lead to some intriguing revelations. Do some follow up questions to know him better.
73. What is the one secret you have never shared with anyone?
To really get to know his deepest, darkest secrets, this question is the one. It is direct and opens up a chest of answers. Discover the skeletons in his closet with this upfront question.
74. Which is the one show you can binge-watch over and over again?
Friends or Seinfeld? Game of Thrones or Grey’s Anatomy? Star Trek or West World? Find out where his allegiances lie.
75. What is your guilty pleasure?
Is he a guy who loves to watch sitcoms or rom coms when he is by himself? Or listens to love songs when he has his earphones on?