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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 | May 16th, 2022
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Having the right questions to ask a guy can make all of your conversations fun, engaging, and interesting. Everybody knows the feeling of an awkward silence – but do you know how easy it can be never to have those again?
If you want to feel confident and natural every time you're out socializing, using a few easily-memorized questions as a means of how to start a conversation with a guy is the perfect move. They open the door for smooth conversations that can make deep connections.
In fact, it's a little-known secret that people love people who ask questions. So take a page from business researchers, muster up your courage, and have the confidence that asking questions is a good thing.
We have everything you need to start asking guys great questions... Today!
via: Pexels / Jack Sparrow
These powerful examples are the best questions to ask a guy, hands down. We've carefully selected only the top of the line, most successful questions to keep your connections fresh and interesting.
Here are the 12 best questions to ask a guy:
It's true that a person's friendships say a lot about who they are – so this question secretly asks guys what they value most about themselves.
Everyone can agree that family is important, so asking about his family will reveal what is important in his life.
If you're feeling brave and up for an open discussion, this one always draws a good response that shows a guy's values.
Questions like this give room for creative expansion and invite lots of follow-up questions as to why they chose those guests.
Tattoos are an incredibly personal thing and a great way to explore someone's deepest-held beliefs.
via: Unsplash / Julia Giacomini
How has someone else helped to make his world better?
Tread lightly with this one, and you can open the door to heart-felt connections over what's not been perfect in your lives.
How patient is he, and for what things? Patience is a virtue, after all.
Or, said another way, what do you keep yourself from doing because of being worried about how people would see you?
What makes life worth living for him?
via: Unsplash / David Mao
Embarrassment can be an easier way to talk about potentially difficult feelings.
Once you ask this one, you can follow up on any answer by asking him to describe it in more detail.
via: Pexels / Maria Orlova
Questions can be a great way to introduce yourself, and the right questions to ask a guy to get to know him can be used right off the bat – or saved for later in the conversation.
Here are the 10 best questions to ask a guy to get to know him:
Our insecurities reveal a lot about our deeper character and how we deal with challenges.
Making connections to the people he knows best can bring you closer together.
A guy's passions will tell you about his drive and direction in life – and be a great way for him to share with you.
via: Unsplash / KAL VISUALS
Is he more than meets the eye? What secret interests does he have?
Nostalgia is a great conversation topic for people of similar age groups.
Camping? Shaving? What is better done without the conveniences of modern technology?
Preserving that childlike joy can be challenging, but definitely makes life more interesting.
A guy's goals will tell you what his motivations are. What makes him persevere in the face of difficulty?
via: Unsplash / S O C I A L . C U T
Is he more of an outdoorsy type, or a stay-at-home guy?
A great follow up question is to ask him how that fear has changed his life, and whether he has ever confronted it.
via: Unsplash / Christin Hume
Are you feeling that spark of interest with a guy you're talking to? Knowing a few questions to ask a guy you like can be an amazing way to take the pressure off of yourself in that situation.
Here are the 12 best questions to ask a guy you like:
Getting him started talking about spontaneous things can lead to the two of you finding your own spontaneous adventure together.
This question lets you know what makes him happiest.
If the feeling of interest is mutual, use this question to get straight to the point!
via: Unsplash / Clem Onojeghuo
It's inevitable that fights happen, and how someone handles them shows a lot about their level of maturity.
Whether you're both night owls or early birds can be an indicator of compatibility.
Bonus points if you can have him teach you the trick!
The classic saying that "the way to a man's heart is through his stomach" still holds true.
If he has, does he have any good stories from it?
via: Unsplash / Avi Richards
Everybody has regrets, so this question asks what he would like to have done differently in his life.
Asking him about how he became who he is can bring you closer together.
Then, can the two of you check one of those items off together?
What does he think his best attributes are? Bonus follow-up: Ask what his biggest weakness is, too.
via: Unsplash / Kelly Sikkema
If you're already happily in a relationship, that doesn't mean you should stop getting to know each other even better. Making a conscious effort to have great questions to ask your boyfriend can keep the relationship fresh and interesting.
Here are the 6 best questions to ask your boyfriend:
Reflecting on both of your positive qualities can be a powerful way to reconnect.
via: Unsplash / Jeremy Thomas
Get right to the point with a strong reminder of how much you care for each other.
Talking about your fears together can bring you closer together and prepare you for a future together.
Celebrating your differences is just as important as enjoying your similarities.
Why not listen to that music more as a way to spend time together?
Have those changes been for the better? Are you both growing as people?
via: Unsplash / a befendo
via: Unsplash / Priscilla Du Preez
Keep things lighthearted and cheerful with these fun questions to ask a guy, and you can be sure that he'll think of you as a fun and exciting person.
Here are the 6 best fun questions to ask a guy:
Just about everyone has a story of being funny and ridiculous as a kid.
Afterwards, you can tease them about being on Santa's list.
Curiosity compels us to explore the world – a great way to encourage his creative side.
Superstitions are a common connection between pro athletes and housewives, and a great topic to gently poke fun at.
After he answers, look up whether you could take a class on it together!
via: Unsplash / Elijah Hail
Say this one with your best poker face, then wait for the laughs.
via: Unsplash / Matheus Ferrero
Getting a laugh out of him can be as easy as having great funny questions to ask a guy. You can practice your timing and stage presence with these funny questions.
Here are the 5 best funny questions to ask a guy:
If you've got forever in the afterlife, you might as well make it interesting.
This highly suggestive question can lead to some good laughs if it's not taken too seriously.
Afterwards, give your best impressions of rude animal voices.
Make him entertain you with this question!
via: Unsplash / Eliott Reyna
Bonus points if you can play Call of Duty together to that soundtrack.
via: Unsplash / Priscilla Du Preez
Thought-provoking, interesting questions to ask a guy can take any conversation into new territory.
Here are the 7 best interesting questions to ask a guy:
How did that advice play out?
Then, how can you encourage him to try that thing?
Money can't buy happiness, but it's certainly more difficult to be sad in a $10,000 hot tub.
This question secretly asks what he thinks his best qualities are.
via: Unsplash / Eliott Reyna
The two of you can brainstorm how to make that day happen together.
Is it true that it's "better to have loved and lost, than never loved at all?"
Guys don't often receive compliments, so this one can bring up great memories.
via: Unsplash / Priscilla Du Preez
These random questions to ask a guy are perfect when you're not sure where the conversation is going, but want to keep talking.
Here are the 6 best random questions to ask a guy:
Does he have an entrepreneurial side?
What is he most curious about the outcome of?
via: Unsplash / Drew Beamer
Is anything "off limits"? What are the boundaries of his humor?
Work life can get very strange, indeed.
Then, can you find that movie to watch together?
Dreams have been a source of curiosity for millennia. What does he think the dream means, too?
via: Unsplash / Priscilla Du Preez
Deep questions to ask a guy bridge the gap between surface-level politeness and the possibility of genuine connection. They're especially good to ask when you feel the start of a great connection, and want to see where it might go.
Here are the 7 best deep questions to ask a guy:
Getting into talks about childhood memories can bring up deep connections to time and place.
via: Unsplash / Robert Bye
How does the future he's imagining line up with yours? How is it similar and different?
What memories does he have from this young love?
How someone handles their life's challenges says a lot about their true character.
The religious world might be divided on this topic, but when someone believes in it, they feel strongly about it.
Sharing fears can be a powerful way of coming together over shared vulnerabilities.
via: Unsplash / h heyerlein
Any question that asks about the past, and childhood in particular, can be a powerful way to inquire deeply about his life.
via: Unsplash / Alexis Brown
Picking the best questions to ask a guy can be simple and easy with these three steps.
Here is how to pick the best questions to ask a guy:
Consider where you're at, what other people you're with, and how much time you have to talk before deciding on the best questions to ask.
In other words, the best questions for an intimate date at a coffee shop will be totally different from the best questions to ask at a loud, crowded concert.
Be sure to introduce yourself before you start asking questions.
Then, use his name when you're asking the questions – it makes it feel personal and genuine.
via: Unsplash / Matt W Newman
Maybe most important of all... Don't overthink it!
When you trust your heart, things will flow more smoothly and naturally, which are both qualities of great conversations.
via: Galtelligence.com
Here is a downloadable and printable List of questions to a guy (right click the image and select Save Image As...) :
Having specific guides can help with any challenges you might face.
So if you need more than just great questions to ask a guy,
We've got you covered:
With all of these great questions to ask a guy, you'll never be at a loss for how to start a conversation with a guy, or how to keep that conversation fun, interesting, and engaging.
No matter what your reason for reading, we hope that you'll use this great information to get out there and start practicing!
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