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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 | March 30th, 2022
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If you’re out on a date and wishing you had some fun questions to ask your boyfriend, you’re in luck! This fun list is packed full of interesting, and creative questions to ask a guy you like, along with some deeper questions to ask a guy you have been seeing for a while!
You probably know how to start a conversation with a guy, but sometimes it can feel like the dialogue kind of stalls out.
These questions will help things going again, and are sure to lead to some fun discussions!
via: Pexels / Jonathan Borba
These are the best of the best questions, great for starting a conversation any time. You don’t have to do them in order, just find a few that sound fun!
Don’t forget to take notes (maybe, later, so it doesn’t feel like a test!) - some of these have great info in them!
Here are the best questions to ask your boyfriend:
What is his definition of happy?
And if it's socks, it may be time to end things… kidding!
Would he be starstruck, or would he start hitting on some issues?
via: Bigstockphoto / Rido81
And how would he fix it?
If so, would he travel randomly, or make a detailed plan?
Maybe it’s video games on his phone, scrolling Insta, or reading a good book.
Get creative - there are lots of weird crime laws on the books!
via: Bigstockphoto / Dmytro Sidelnikov
If you want some questions to ask a guy to get to know him, this is the list for you! Find out what he likes, dislikes, what makes him tick!
Here are questions to ask your boyfriend to get to know him:
What can he buy that makes him happy?
What would you do if you randomly ran into them?
via: Unsplash / Karl Fredrickson
It can be from a book, movie, comic, tv show - player's choice!
Is he a city mouse or a country mouse?
via: Unsplash / Max Bender
When thinking of things to ask your boyfriend, it's a great idea to ask how he feels about taking contemplative time.
via: Unsplash / Nathan Dumlao
Remember to cross your heart, promise not to tell!
Reassure him that you’ll never tease him about this.
via: Pexels / Lê Minh
So, you’re on a date and trying to get to know each other better, but the conversation gets a bit stuck. No fear, help is here!
These are some amazing, fun questions to ask a guy that will get you guys connecting in a whole new way!
Here are fun questions to ask your boyfriend:
Was it as good as he hoped, or more awkward than he expected?
Are there parts of it he doesn’t like touched? This might just be one of the best things to ask your boyfriend.
Maybe something silly, like twisting your hair.
via: Unsplash / Gianandrea Villa
Ask how his parents reacted to other girlfriends.
Does he like to watch sad movies or does he feel manipulated?
via: Unsplash / Mesut Kaya
Something thrilling like ice cream or decadent like lava cake?
Someone funny? Serious? Devastatingly handsome?
via: Bigstockphoto / jovanmandic
Looking to add a little silliness in your relationship? That’s great! Studies show that couples that have fun together stay together longer!
Try using these funny questions to ask a guy to get some good, wholesome wit going on!
Here are funny questions to ask your boyfriend:
And how did he recover??
Besides the birthday cake, of course!
Have him describe why it was so hysterical.
via: Unsplash / Giorgio Trovato
Would he wear it now as an adult?
via: Unsplash / Arun Sharma
Was it from a loving friend or a bully?
Which language does he think is the hardest to learn?
How often does he play pranks? What if other people don’t like them?
via: Unsplash / Omar Lopez
via: Pexels / Immortal shots
Asking people questions about themselves helps them feel like you are truly interested in them. These interesting questions to ask a guy will send him the message that you want to know all there is to know!
So pick a few and become an expert on your new favorite subject- your guy!
Here are interesting questions to ask your boyfriend:
Maybe its a food, a sport or a TV show everyone else loved.
On a scale of zero to manly, let’s rate things.
via: Pexels / tear cordez
How can you make him more comfortable with those?
Does he feel like that’s not enough? Or too many?
Has it broken up a relationship for him before?
via: Unsplash / Romain Lours
If not, what does he think healthy relationships look like?
Would that be too hard to handle? How would he measure?
via: Unsplash / Josh Hild
Running 5k’s Thanksgiving morning? Coordinating tattoos?
via: Bigstockphoto / Saharrr
These deep questions to ask your boyfriend will get everyone moving in a more serious direction, stat! Make sure you handle these questions with care - there is a lot of vulnerability being spoken here.
And on that note, don’t be afraid to respond with your own answer. You being open helps create a culture of trust.
Here are deep questions to ask your boyfriend:
This would be a good answer to write down and remember.
Is it something that comes naturally or something you guys have to work at?
via: Pexels / Pixabay
What is the ideal alone/together ratio?
What about someone else? How would he feel about someone sacrificing for him?
What will they look like after this life?
What makes him feel loved, safe, and seen in those moments?
via: Bigstockphoto / LightField Studios
How can we keep a balance with all of its benefits?
Did he learn them the easy way or the hard way?
via: Pixabay / VladBitte
How about some sexy questions to ask your boyfriend that will drive him crazy and possibly get him in the mood to do whatever you want. With these questions, you'll definitely be in control of the situation.
Here are sexy questions to ask your boyfriend:
Take notes, and use this on him the next time you're in the mood.
This is definitely a question you already know the answer to.
Let him show you, rather than tell you.
And tell him which you prefer him to wear, also.
via: Pexels / cottonbro
via: Pexels / Ria Patel
So, there are almost a million questions here, how do you even start? I’ve made a quick little guide to help you make the most of this extensive list of queries.
Here is how to pick the best questions to ask your boyfriend:
via: Bigstockphoto / Estradaanton
There are times for having deep and probing conversations, and there are definitely NOT times. Make sure you and your guy are in a good space, aren’t having a little spat, not struggling with a big decision, and aren’t tired, hungry, or lonely.
You’ll have the most fun and have better conversations when you’re hearts and minds are open to connecting. Trust me, it’s worth the wait.
via: Unsplash / Priscilla Du Preez
Don’t just start at the top and start blasting away - some of these questions are more suited to a serious relationship. Don’t scare away a potential partner by asking him to tell you his darkest secret on your first date.
Start slow and easy, and as intimacy builds, feel free to start moving into deeper waters.
via: Unsplash / Milan Popovic
I mentioned it earlier - be open yourself with answering these questions. This shows your guy that you are willing to create a space that is safe for these deep questions!
And be careful with his answers - when he tells you his insecurities or about a happy memory, make sure to thank him for sharing his thoughts, and NEVER use it against him in a fight.
Here is a downloadable and printable List of Questions To Ask Your Boyfriend (right click the image and select Save Image As...):
via: Galtelligence
Now, you have more questions to ask your boyfriend than you know what to do with! Next time you’re trying to remember how to start a conversation with a guy, just break out this handy list and find some great conversation kindling!
Search through the list whenever you think "I wish I had questions to ask my boyfriend". Great conversations are just ahead - have fun!
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