53 Personal Questions To Ask A Guy – Spark great conversations.
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See, it’s that personal touch that makes it so simple and easy to know how to start a conversation with a guy, and learn enough about him to continue a fun and interesting conversation.
When you’re ready to make things a little more intimate between the two of you, these personal questions transition perfectly into deep questions to ask a guy, too. Why? Because the more he responds positively to your personal questions, the more deep and meaningful the conversation can become.
Really, all of these questions to ask a guy can be made personal in a way that is welcome and inviting — not awkward or boring! If you’re ready to learn how, use this guide as a constant resource to keep your conversations interesting, engaging, and heart-warmingly personal.
The all-time best personal questions to ask a guy share one thing in common: They’re exceptionally versatile. This means that you can memorize and practice a few of them, and be ready for just about any situation!
Here are the 10 best personal questions to ask a guy:
1. What kind of food do you like?
Sharing food might be the quickest way to get to know each other. A great follow-up for this one is asking if he has a favorite restaurant you could go to together.
2. What did your last relationship teach you?
Every relationship is a learning experience. What did he take away from his experiences?
3. Do enjoy one on one outings or do you prefer big groups?
This question asks just how personal he likes to keep his social time.
4. If a psychic could tell you what will happen in the future, what would you want to know?
Love them or hate them, just about everybody has a strong opinion about psychics. What are his thoughts on the matter?
5. Which parent are you closer to and why?
It’s been said that your parents are the most important people in your life. His relationship with them will say a lot about him as a person, too.
6. If money and career were no object, what would you really want to be doing?
Or, said another way: What are you most passionate about?
7. What’s something you’re really good at?
Guys love talking about what they’re really good at, if you give them the opportunity.
8. Where do you go when you need some inspiration?
Whether a favorite coffee shop, the local pub, or deep into the woods, this question speaks to his place of inner stillness.
9. What are you passionate about in life?
Discovering what you love most can be an adventure in its own way. How did he find his passion?
10. If your home was on fire, what would you grab on the way out?
This question asks somewhat indirectly what is most important to him.
If you’re feeling particularly bold and brave, questions to ask a guy to get to know him can be taken in a very personal direction. A little risk can definitely be worth the reward of knowing each other better, faster.
Here are 8 personal questions to ask a guy to get to know him:
11. Do you think God is real, and why?
Religion can be a touchy topic, so approach this one gently!
12. If you had a chance for a “do-over” in life, what would you do differently?
Regret is a common experience for people of all walks of life; this question cuts straight to the heart of things.
13. If you could only keep five possessions, what would they be?
What we own becomes a part of us — our “baggage” — so what is it that he holds most dear?
14. Are you a morning or a night person?
If you’re interested in seeing where things go with him, it helps to be on similar schedules.
15. What do you think is humankind’s greatest invention?
Cell phones? Sliced bread? His answer will tell you what area of life is most interesting to him.
16. Are you a mountain or a beach person?
Either way, this question can lead to the thought of planning a trip together.
17. What is your take on astrology?
Total fallacy? Deeply true? This one can be polarizing, to say the least.
18. How would your friends describe you?
A person’s friends are more likely to be brutally honest about their positive and negative attributes.
When you start to feel like there’s something special happening between you two, that’s the perfect time to pull out these questions to ask a guy you like. Make it personal, keep it lighthearted, and you’ll be well on your way to being even closer to each other.
Here are 9 personal questions to ask a guy you like:
19. What do you do on your commute to/from work?
Because this time is so often spent alone, this is a perfect question to learn about his personal life.
20. Have your ever disliked something and then changed your mind?
Our habits and preferences change over time, so this question digs into his past a little bit.
21. What annoys you most?
Pet peeves are like nails on a chalkboard: Impossible to ignore.
22. Do you like going to parties?
Is he more introverted, or extroverted? How does this match up with you?
23. Are you a lazy person or active person?
Both are definitely okay, but it’s good to be on a similar page with energy levels.
24. What counts as a perfect morning to you?
Who knows, maybe you might be able to share one just like it someday?
25. How do you want your life partner to be?
If he hasn’t even thought about this before, it’s a good sign that he’s not ready to commit to a relationship.
26. What is the kindest thing anyone has ever done for you?
Kindness makes the world go around. Did he pay it forward, too?
27. Do you believe in having a “five-year plan”?
Sure, it might be the responsible thing to look into the future… But is it the most enjoyable way to live life?
It doesn’t always have to be super serious — especially with these personal but fun questions to ask a guy. You can get to know him just as well through humor and lighthearted banter as through more serious, deeper conversations.
Here are 6 personal but fun questions to ask a guy:
28. When was your first kiss?
Most often, our first kiss is an innocent memory — usually with a good story attached, too.
29. Are you into after-work happy hours?
And if so, why not go out to one together?
30. Is there a smell that instantly relaxes you?
Maybe it’s fresh cinnamon rolls, or his favorite coffee shop, or the scent of a well-worn book.
31. What is your ideal night?
Night time is the right time for fun and hijinx, after all.
32. What would be a fun date that only costs $20?
Afterwards, pull a power move by taking $10 out of your wallet and giving him a curious look!
33. Do you think flying or mind reading is a more functional power?
Because every guy has dreamt of having superpowers; don’t let anyone tell you any different.
Embrace your inner comedian with personal yet funny questions to ask a guy, and you just might find yourself as the center of his attention. Humor, after all, is an extremely attractive trait to most people.
Here are 6 personal yet funny questions to ask a guy:
34. What’s the worst pun you know?
Turnabout is fair play. Why not trade your best dad jokes?
35. Have you ever lied to a priest, preacher or holy man?
If yes, give him a hard time until he shares the story!
36. How far do you think black humor should go?
And, more importantly, does this match up with your own thoughts about black humor?
37. What would you do after your boss fires you?
Revenge can be sweet… And exceptionally funny, given the right situation.
38. What is the stupidest way to die?
Need some material? There was a whole TV show about it.
39. What weird or useless talent do you have?
Of course, after he tells you, he has to demonstrate as well.
Testing the waters to see how interested he is can be accomplished with these personal but flirty questions to ask a guy. Watch for signs of interest like turning towards you, putting a lot of effort into his answer, and playfully joking with you.
Here are 4 personal but flirty questions to ask a guy:
40. Do you think people are made for each other?
Does he believe in the idea of “soul mates”?
41. If your partner had close friends of the opposite sex, how would you feel?
This question is asking whether he might be the jealous type.
42. What do you do when you can’t go to sleep?
Nighttime habits can be very personal, so asking about this can make things intimate very quickly.
43. What is the best gift a partner could give you?
Be sure and take note of this one, and save that information for if things start to click between you two.
Stay away from boring or controversial topics like politics or religion if you want to keep things fun and interesting. Most of the time, the best interesting questions to ask a guy will come up naturally during your conversations — but it never hurts to prepare yourself with even more for when the time is right.
Here are 5 personal interesting questions to ask a guy:
44. Have you anything off of your bucket list yet?
Your bucket list is everything you want to accomplish in life, which is always of interest to a guy.
45. Can you tell me a story about a scar you have?
This one is great because every scar has a story, no matter how silly or serious.
46. Can you sum up your life’s philosophy in one sentence?
Even if he can’t, watching him try to will certainly be interesting.
47. Do you love yourself?
Self-love is a matter of self-esteem, and you know what they say: You can’t love someone else until you love yourself!
48. On days when you don’t feel energetic, what do you do?
Nobody is at their best 100% of the time; this question lets you relate to each others’ flaws, too.
All of these questions are hand-picked to be totally out of the box. The perfect random questions to ask a guy are all about catching him a little off-guard, so you know the answer you get will be genuine.
Here are 4 personal but random questions to ask a guy:
49. What’s the worst piece of advice you’ve ever been given?
And did he act on that advice? If so, what happened?
50. Have you ever had a psychic reading?
If he has, what did the psychic “reveal” to him?
51. Have you ever unplugged from the Internet for more than a week?
In our tech-addicted world, this question can bring up times closer to nature for a lot of guys.
52. If you were heading out on a road trip right this minute, what would you pack?
It’s a question of preparedness — or a willingness to play things fast and loose.
53. What are you most grateful for, right now, in this moment?
Bring it back to the here and now with this powerful question.
Picking the right personal questions to ask him is mostly about context. That means your 5 W’s: Who? What? When? Where? Why?
Here is how to pick the right personal questions to ask a guy:
1. Who, specifically, are you talking to?
Is he someone you’ve just met? A friend of a friend? Long-time acquaintance? The more social connections you have, the easier it is to ask a variety of questions.
2. What does he like?
Take note of things that he seems to care about (clothes, sports, food, etc.), and pick questions to explore those areas more in-depth.
3. When are you two going to see each other next?
Even if you’re just getting to meet a guy for the first time, setting up a time to see each other again casually means you can take your time and not feel rushed in a conversation.
4. Where are you at?
Pick questions to ask based on the environment you’re in. Is it just the two of you, where you can get deep? Or are you in a crowded café, where it might be embarrassing to share so openly?
5. Why are you curious about him?
Always keep your initial curiosity in mind, and choose questions that stoke that fire.
Downloadable List of Personal Questions To Ask A Guy
Here is a downloadable list of Personal Questions To Ask A Guy (right click the image and select Save Image As…):
More Great Ways To Talk to Guys
When you’re looking for something more specific, it’s a good idea to keep things fresh with questions from another angle. That way, you can be sure that your conversations with always stay interesting and engaging.
We’ve got you covered:
- If you need help figuring out the best way to suggest a date, check out how to ask a guy out and study up.
- Need something a little bit more flirty? Our guide on how to flirt with a guy has everything you’re looking for.
- When you’re hanging out on the couch with your phone, of course you might be wondering: “Should I text him?”
Even if you’re starting with no idea of how to get more personal, this guide gives you all the personal questions to ask a guy that you might need to know. If you’re still feeling curious for more, we have amazing lists of questions to ask a guy (including deep questions to ask a guy), and a guide for how to start a conversation with a guy in case you’re feeling nervous.
Either way, you’ve got this! Practice a few of these questions to make it that much easier to project your natural confidence.