Fun Questions to Ask a Guy You Like During a Date

Are you interested in this smart, attractive and just perfect at everything man, but have no idea how to approach him? Fret not as we prepared a list of top-20 questions to ask a guy you like. With these tips, you can keep your conversation going and make it exciting for both of you. 

But before we start, please remember, that every man has his own unique personality, so pick the topic wisely and use your natural charm to interest him.

The Ultimate List of 20 Questions to Ask a Guy

If you want your date to go well, try to ask a guy the following questions. 

#1: Do you have a motto, quote, or mantra?

It doesn’t really matter whether it’s something deep and profound or just a daft quote from their favourite movie, this is a light-hearted question that will also give you a peek at their real character.

#2: Do you have any special hidden talents?

Everyone has to be good at something, right? This is a great way to break the ice and give the boy a chance to show off. Their party trick may be a little quirky or weird, so it’s one that could get you both laughing!

#3: Are you more of a lark or a night owl?

If things were to progress, it’s not ideal if you like to fall asleep at 9 pm and rise at 5 am while the guy prefers to wait until 1 am or later to hit the pillow. Knowing whether you both have the same circadian rhythm is a good sign. 

#4: Is there anything that always makes you laugh, even when you’re feeling down?

Chatting about fun subjects can liven up any date. Talking about things which make you laugh will put a smile on your face – and that can be infectious.

#5: Did you have any nicknames when you were younger?

If these were truly awful, they might not want to share these, so before you ask just consider whether there’s anything that may have made him a target for bullies. If not, ask away – but be prepared to share your own childhood nicknames in return!

#6: Do you believe in the paranormal?

If you’re glued to the latest episode of Most Haunted, you could have a fascinating debate about whether those spooks really exist.

#7: If you were going to join the X-Men, what superpower would you have?

This is a great one for the geeks. With all the boring superpowers already claimed, such as strength, flight and invisibility, there’s plenty of scopes left to get creative!

#8: Is there anything that you enjoyed doing once that you wouldn’t do again?

This question could give you all sorts of answers from skydiving to something rather more risqué! Only include this one if you’re prepared to venture into X-rated territory…

#9: Are there any first-world problems that drive you bonkers?

Whether it’s drivers not indicating or ring pulls that always snap off, we’ve all got pet hates which we secretly know are trivial. Find out what makes lover-boy tick with this revealing question. 

#10: What’s your favourite place to get take-out food?

Who doesn’t love a takeaway from time to time? The chances are you’ll have plenty in common. However, if you love a donor kebab and he’s a committed vegan, there may be troubled waters ahead. 

#11: What celebrity would make the worst dinner guest?

Everyone always asks who would be the best dinner guest, so why not turn it on its head and find out who would be the absolute worst! Whether you stick to current celebrities who are alive or include dead folk of the past, the choice is yours. 

#12: What rule would you introduce to social media, if it were possible?

We love it and hate it in equal amounts, but social media is almost impossible to ignore. If he had the power to change one thing, what would it be? You could suggest everything from filters on profile pics through to an instant ban for attention-seeking. The only question is with some many minor internet grievances, what will he pick?

#13: What celebrity crush will you never understand?

While a large percentage of the population might drool over Kim K’s oversized assets, your guy might not be a fan. Or perhaps he doesn’t see the appeal of the earnest Emma Watson. Whoever it is, you’ll learn of a lot about what he finds attractive. 

#14: What’s your favourite moment in each day?

It might be the relaxing cup of coffee in the morning, or perhaps a beer at the end of the day. This question is uplifting as it can help you to think about the things which you take for granted. 

#15: What animal would be the worst to meet in the jungle?

This is one of those questions which sounds a little bonkers but could produce a fascinating conversation, even if it could be a little macabre!

#16: If you could domesticate any animal in the world, what would it be?

This is just a plain funny idea to discuss. Whether you imagine domesticating a lion, hippo, or a sloth, the conversation could be hilarious!

#17: What’s the best podcast in your opinion?

If things don’t work out, at least you’ll have a new podcast to check out!

#18: Would you ever travel overseas by yourself?

Questions shouldn’t be designed to trip someone up; they’re just a chance to find out more about a boy. There’s no right or wrong answer; it’s just interesting to see what their approach to life is like. 

#19: What do you think happens after you die?

If you’re the kind of girl who loves deep and meaningful conversations, this is the perfect question to ask. Just remember to judge the mood right to raise this kind of subject; otherwise, it could be a real buzz-kill. 

#20: Do you want another date?

If you feel as if the date has gone well, don’t be shy about asking whether he wants to meet up again. Rather than hanging on anxiously waiting for a call or text, take the bull by the horns and ask him outright. Whatever the answer, it’s better to know! 

All of these questions can be a big help when you’re trying to get to know a boy. 

Do you have any stories of your own or any more interesting topics to raise on a date? Share the article on your social media and tell us about your experience! 

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