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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by Jasper | June 4th, 2021
via: Bigstockphoto / AntonioDiaz
Personal questions to ask a guy, is a great way to develop a relationship with someone you're interested in. Get to know him more deeply with these questions.
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.
via: Bigstockphoto / Dean Drobot
What are personal questions to ask that's guaranteed to give you a good time? Well, 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:
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.
Every relationship is a learning experience. What did he take away from his experiences?
This question asks just how personal he likes to keep his social time.
Love them or hate them, just about everybody has a strong opinion about psychics. What are his thoughts on the matter?
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.
via: Unsplash / wonsung jang
Or, said another way: What are you most passionate about?
Guys love talking about what they're really good at, if you give them the opportunity.
Whether a favorite coffee shop, the local pub, or deep into the woods, this question speaks to his place of inner stillness.
Discovering what you love most can be an adventure in its own way. How did he find his passion?
This question asks somewhat indirectly what is most important to him.
via: Bigstockphoto / fxquadro
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. If you're asking what are personal questions you can ask to get to know a guy, you're in the right place.
Here are 8 personal questions to ask a guy to get to know him:
Religion can be a touchy topic, so approach this one gently!
Regret is a common experience for people of all walks of life; this question cuts straight to the heart of things.
What we own becomes a part of us – our "baggage" – so what is it that he holds most dear?
If you're interested in seeing where things go with him, it helps to be on similar schedules.
via: Unsplash / Danielle MacInnes
Cell phones? Sliced bread? His answer will tell you what area of life is most interesting to him.
Either way, this question can lead to the thought of planning a trip together.
Total fallacy? Deeply true? This one can be polarizing, to say the least.
A person's friends are more likely to be brutally honest about their positive and negative attributes.
via: Depositphotos / leungchopan
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:
Because this time is so often spent alone, this is a perfect question to learn about his personal life.
Our habits and preferences change over time, so this question digs into his past a little bit.
Pet peeves are like nails on a chalkboard: Impossible to ignore.
Is he more introverted, or extroverted? How does this match up with you?
via: Unsplash / Emmanuel
Both are definitely okay, but it's good to be on a similar page with energy levels.
Who knows, maybe you might be able to share one just like it someday?
If he hasn't even thought about this before, it's a good sign that he's not ready to commit to a relationship.
Kindness makes the world go around. Did he pay it forward, too?
Sure, it might be the responsible thing to look into the future... But is it the most enjoyable way to live life?
via: Bigstockphoto / manupadilla
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:
Most often, our first kiss is an innocent memory – usually with a good story attached, too.
And if so, why not go out to one together?
Maybe it's fresh cinnamon rolls, or his favorite coffee shop, or the scent of a well-worn book.
Night time is the right time for fun and hijinx, after all.
Afterwards, pull a power move by taking $10 out of your wallet and giving him a curious look!
Because every guy has dreamt of having superpowers; don't let anyone tell you any different.
via: Bigstockphoto / Dragon Images
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:
Turnabout is fair play. Why not trade your best dad jokes?
If yes, give him a hard time until he shares the story!
And, more importantly, does this match up with your own thoughts about black humor?
Revenge can be sweet... And exceptionally funny, given the right situation.
Need some material? There was a whole TV show about it.
Of course, after he tells you, he has to demonstrate as well.
via: Bigstockphoto / LightField Studios
What are personal questions to ask when testing the waters to see how interested he is? Well, these personal but flirty questions to ask a guy can help you with that. 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:
Does he believe in the idea of "soul mates"?
This question is asking whether he might be the jealous type.
Nighttime habits can be very personal, so asking about this can make things intimate very quickly.
Be sure and take note of this one, and save that information for if things start to click between you two.
via: Pexels / mentatdgt
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:
Your bucket list is everything you want to accomplish in life, which is always of interest to a guy.
This one is great because every scar has a story, no matter how silly or serious.
Even if he can't, watching him try to will certainly be interesting.
Self-love is a matter of self-esteem, and you know what they say: You can't love someone else until you love yourself!
Nobody is at their best 100% of the time; this question lets you relate to each others' flaws, too.
via: Pexels / cottonbro
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:
And did he act on that advice? If so, what happened?
If he has, what did the psychic "reveal" to him?
In our tech-addicted world, this question can bring up times closer to nature for a lot of guys.
It's a question of preparedness – or a willingness to play things fast and loose.
Bring it back to the here and now with this powerful question.
via: Pexels / Andrea Piacquadio
If you’re really serious about a guy, then it’s time to think about a few personal questions to ask a guy over text. These questions will reveal a lot about him.
Here are 4 personal questions to ask a guy over text:
Ah, the old debate about the “noble lie.” This philosophical question is bound to spark a real conversation.
If he’s speaking from personal experience, you’ll probably hear some pretty personal information when he answers this question. However, you’ll also learn how he views relationships as a whole.
via: Pexels / Polina Zimmerman
You’ll learn a lot about a guy when he tells you whether or not he believes in second chances. Are some things unforgivable, like cheating? He probably has strong opinions about this.
If you’re looking for a driven, goal-oriented man (like most women are), you’ll need to figure out his priorities in life. If he’s just drifting in the wind, don’t expect an encouraging answer.
via: Pexels / cottonbro
Ready to get really deep? Check out these deep questions to ask a guy, and make sure that you’re learning about the real guy underneath it all.
Here are 5 deep and personal questions to ask a guy:
This reveals so much about a guy - if you know what to listen for. Almost everyone is closer to one parent rather than the other, and their decision is definitely based on their underlying personality.
With this question, you’re basically asking about his pet peeves. Who knows? Maybe you two share a lot of these features when it comes to this question.
Most people have pretty strong opinions when it comes to this topic. You probably do too, and that’s why it’s a great question to ask if you want to know if he’s right for you.
via: Unsplash / Gus Moretta
People are very split on this topic, and you’ll learn a lot about his priorities and values when he answers. Expect a lengthy and satisfying discussion.
It takes some people their entire lives to learn that there are some things you should never apologize for. If you want to know whether he’s there yet, ask him this question.
via: Bigstockphoto / Eldar Nurkovic
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:
via: Bigstockphoto / AntonioDiaz
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.
via: Unsplash / Hannah Olinger
Take note of things that he seems to care about (clothes, sports, food, etc.), and pick questions to explore those areas more in-depth.
via: Unsplash / Jealous Weekends
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.
via: Bigstockphoto / AntonioGuillem
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?
via: Unsplash / Tyler Nix
Always keep your initial curiosity in mind, and choose questions that stoke that fire.
Here is a downloadable and printable List of Personal Questions To Ask A Guy (right click the image and select Save Image As...):
via: Galtelligence.com
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:
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.
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