Cute Questions to Ask a Guy

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If you ever feel tongue-tied when you try to talk to a guy you have a crush on, don’t worry. Awkward silences happen to everyone at some point. You can combat the phenomenon by using a few interesting tips to keep a conversation going and show your interest simultaneously.

Asking questions is the quickest way to learn about someone, and it shows the person you’re talking to that you want to get to know them better. A study from Harvard Business School even shows that asking someone questions about themselves increases the chances they will like you.

But what questions should you ask the guy you like? In this article, we’ll lay out all the cute questions to ask a guy if you want to pursue him soon. Use these questions to get to know a guy easily and deeply. Learn his likes and dislikes and focus on which questions may pertain to your guy better than others.

What Makes You Feel Alive?


Everyone has something thrilling and inspiring in their lives that makes them come alive. A fun question to ask a guy you’re interested in can help you better get to know someone even if you already think you know the answer. You never know, he may have a hidden passion you didn’t know about yet.

What Do You Consider Your Favorite Part of a Woman?

Guys all have their preferences when it comes to their “type” of woman. Some people are all about those lady curves, while others enjoy pouty lips or dreamy eyes. It may sound physical, but for guys who are meeting a new potential mate, research shows attraction is very much a visual response. So, don’t worry if he says his favorite part is your chest. He’s not a pig. He’s probably a normal guy.

What is Your Idea of the Most Attractive Qualities in Others?

Like the previous question, asking a guy you have a crush on about the qualities he finds most attractive in other people can help you figure out what he values. It will show you what type of guy he truly is as well as what he may value in you as a friend or a romantic interest.


Plus, unlike the last question, this option opens the conversation up to being about both sexes. Doing so helps free up the pressure and allows you to focus on qualities rather than body parts, moving into a deeper conversation than the physical level.

What’s Your Ideal Date?

Dating activities can range widely, from sporty and adventurous to romantic or lazy. Some couples prefer to cook and open a bottle of wine at home. Others might want to go high-speed go-kart racing to get their adrenaline pumping. Whatever he enjoys, his answer to this question will let you know what you can spend time doing together.

If you don’t enjoy staying in to watch movies on the couch together and are more of a go out dancing gal, maybe it’s not meant to be for you.

What’s the Best Thing to Happen to You So Far?

Another of our favorite questions to ask a guy is about his life before meeting you. Favorite memories can clue you into what your guy holds dear to his heart. They’re also an excellent way to get better to know what he was like as a child or lead into other questions about what makes him happy as well.

Who Do You Admire and Why?


Who your guy most admires, whether he has met them in person or not, lets you know two crucial things: his values and aspirations. The person can even be fictional characters from pop culture, tv, or movies.

Everyone has a goal in life, and people they look up to that meet how they see their future selves. Understanding who he admires can help you support him to become the best version of himself someday. You’ll learn about his values and what he thinks is right.

Do You Believe in Soulmates or Love at First Sight?

Either of these questions can let you find out how much of a romantic your guy is. People all have different views on love, and you should find a partner who has a similar viewpoint on love like you.

What Makes You Smile?

Finding out what makes the guy you like smile allows you to help him smile more. If he like knock-knock jokes, research some options you can text him. Whatever makes him smile, studies show that friendships (and especially romantic relationships) get off to a better start if you smile more.

Who Was Your First Crush, and Why?


He might blush if you ask him about his first crush but reminiscing in the past can be fun. It allows you to see what first made his heart yearn for another person and get another look at what his friends attractive in a partner. Use this question as an ice breaker to learn more.

What’s the Best Thing About Relationships?

Some guys love being in a relationship, while others wind up there by chance. A relationship type of guy enjoys being a part of a couple deep down to his core, and you can expect this guy to prefer relationships to being single. Not everyone is the same though.

What Movie Would You Re-watch for Eternity?

You can bet that if he’s willing to re-watch the same movie repeatedly that he truly loves that movie. If you’re together for a long time, you’ll probably watch his favorite movie multiple times. Make sure it’s a flick you’re willing to watch for the rest of your life, or at least give it a chance. You’ll better get to know his preferences and maybe even learn something new.

Cute questions to ask a guy can sometimes help you figure out date ideas too. Asking about his favorites, like movies, allows you to watch new things together if you haven’t seen it too. Let him share his favorites with you and share yours as well.

What’s Your Favorite Song?

Music is an excellent icebreaker to help you better get to know someone new. Like other questions on this list about preferences and favorites, talking about your favorite songs and artists can help you bond and give you date night ideas. Maybe you’ll later surprise your guy with tickets to his favorite band.

What Superpower Would You Want?


We all secretly wish we had a superpower. Although this is a silly question, you don’t have to ask only serious questions to get better to know someone. Let your imagination wander.

What Are Your Fears?

When people open about what scares them, they also start to trust more. Irrational and reasonable fears alike can take the conversation to a deeper, revealing level. You might get to know what makes you guy tick or learn about something traumatic in his past with this question.

What’s Your Favorite Thing About Yourself?

Unless your guy is highly confident, he might seem a little embarrassed with this question. It’s hard for most people to talk about the best things in themselves openly, especially if you’ve only recently met. However, the answer can help him think about who he is deep down.

Do You Enjoy When a Woman Makes the First Move?

While some guys are more on the traditional side, others prefer bold women. You can find out where your guy’s preferences reach in his mate and see what a relationship might be like between the two of you. Confident women make scare away shy men, but others may prefer a lady who comes on stronger instead of guessing what she might want.

What Are Your Personal Goals and Hobbies?

One of the best questions to ask a guy, you should use this question for anyone you want to date. He has goals and hobbies that may not have anything to do with you, and you should know about what he enjoys the most if you want to be in his life.

Where Do You See Yourself in Five Years? Ten?


He may throw out a wide range of answers for these questions, but they can let you see how he views his life aligning in the future. If he has no goals for the next five or ten years, run. A guy who doesn’t know where he wants his future to go doesn’t have a plan.

Do You Like to Cuddle?

Hopefully, his answer to this question aligns with yours. Not everyone likes to cuddle, but many couples prefer someone they can feel comfortable snuggling up to on the couch. Science shows there are tons of powerful benefits to cuddling, from improving sleep and happiness to easing chronic pain and your risk of heart disease.

What’s the First Thing You Noticed About Me?

As mentioned above, this question might prompt him to list off a few of your physical features first. Men are highly visual creatures, so the first thing he probably noticed that you might be a body part. He might catch you off guard by answering with something less vulgar, though, like your smile or your eyes. His answer will show you what he finds attractive. You can later play up that feature for his benefit.

What’s Your Highest Accomplishment So Far?

Accomplishments help us feel awesome about ourselves and our lives. See what your guy has accomplished and learn his mission for success. The things that make him strive to achieve help him feel good. Show interest in what he enjoys.

What’s the Best Way to Maintain the Spark in a Relationship?

Keeping a relationship alive for a long time isn’t about luck or finding the right person. It’s hard work and effort. Find out how he feels about these common issues couples will face over time.

What Was Your Childhood Like?


Understand where your guy grew up and what it was like to better learn his personality and quirks. You can learn so much about why he became who he is today from his childhood. It’s a must-ask question for a guy you just met and considered dating.

What Makes You Feel Insecure?

Personal questions help you target who your guy is. Everyone has insecurities, and while they’re difficult to discuss, knowing someone else’s low points are ideal for they show up. Eventually, they will come to light anyway. If you already know what’s going on, you will be better ready to deal with the situation during the critical moment.

What Do You Expect in a Romantic Relationship?

Relationships differ for everyone. Find out if your guy has the same idea about romantic relationships as you do before things get too serious, or you might have a mess of unmet expectations on your hands later. Clarify how you want the relationship to go in the beginning.

Do You Want Kids? Marriage?

Many couples today avoid talking about marriage and kids until “the time is right” or when their relationship seems more serious. However, don’t wait. Some people don’t want to conform to these norms in our society, and they might not change their minds with time or even because they love you. You need to make sure your partner wants the same things as you before you become shocked later.

What Expectations Do You Have for Yourself?

Whatever answer your guy provides, this question helps you see what he might expect from you as well. Learn what expectations he holds himself to and ask your crush early.

Do You Have Career Goals?


Is your guy planning to move across the country to a career choice, or would he take a job traveling the globe? Learn how he wants to spend his working days and where he sees his career going in the future. He might spend a lot of time at work, so it’s interesting to know where his boundaries are now.

What Are Your Friends and Family Like?

The people who have been in his life before you met probably mean the world to him. Learn as much as you can about who they are early on, and you can use the information to help you later talk to them when he introduces you to his loved ones.

What Would You Do with a Million Dollars Cash?

Among our favorite cute questions to ask a guy is this gem. If someone handed your love interest a million dollars in cash right now, what would he do? The answer may reveal what he likes, dreams, and feels interested in. You can tell if he’s materialistic, or if he’s the type of person who would rather spend money on experiences over things. His adventurous spirit may show.

If You Moved Anywhere, Where Would it Be?

An easy question that helps you better get to know someone. The answer you receive from this question shows you if the guy you’re interested in prefers an urban setting or perhaps wants to move away from your current location someday. If you’re tied down to your roots, you may not feel the same way about moving. It’s better to find out early how your preferences align.

Do You Like Your Job?

How your guy feels about his current job can show you how he sees his future. He might feel passionate about his career or be stuck in a job for survival momentarily. Either way, you’ll learn about his goals and plans to achieve a better future.

Can You Describe Yourself in a Single Word?


Ask a guy to describe himself in one word and see if he gives you a simple word or a compound. Short words show he may have fast, skilled characteristics, while a compound word might make him more complicated. If it takes a guy a long time to come up with an answer, he might not have thought about his skills and the meaning of his life yet.

What’s Your Favorite Food?

Another excellent way to find date night ideas for a new relationship is to ask about favorite things early on. Food is one of the easiest things people bond over. It also says a lot about our values. Some people prefer foods to maintain their health and physical appearance, and others want a gourmet meal to make their taste buds melt – even if it means they might gain a few pounds.

This question is another way to find out if your guy likes to cook at home or go out to a restaurant. You’ll be able to easily predict if you’ll spend hours in the kitchen together or learning new culinary techniques. You can even make his favorite meal for him as a date night idea.

What’s Your Favorite Childhood Character?

A funny question to ask a guy, you can learn more about his likes and childhood by getting specific. What characters did he prefer, and why?

What’s Your Favorite Pet?

If you’re an animal lover, this question may be vital for you to ask. It’s just another cute question to ask a guy, but the answer can help you see how the two of you match up. If he’s allergic to cats and you have five at home, it might not work.

Would You Rather Fish or Hike?

Another way to find out how he enjoys spending his time, asking this question shows you how your guy likes to unwind. Some people find fishing to be calm and relaxing, while others prefer adventure. See what he enjoys and if it aligns with you.

When Do You Think Two People Become Intimate?

Thought-provoking questions about relationships can help you get your guy thinking about how he feels about you. He will also reveal how he thinks the steps in a relationship transpire and any other thoughts he might have on romance and intimacy.

Do You Think Women are Equal to Men?

A crucial question for women to ask a guy they just met, find out what he thinks about equality. You wouldn’t want to marry a guy only to find out much later that he wants you to quit the job you love and become a stay at home mom. If cooking and cleaning isn’t your jam, you must find out now if that’s what he wants.

What’s the Craziest Thing You’ve Done?

Does your guy have a wild side? You can find out the easy way by asking him about the crazy stuff he may have done early in the relationship. You can find out more about his past and see what insanity he might be trying to hide.

What’s Your Favorite Car or Sport?

If the man you’re interested in favors manly things like sports or cars, try asking him about his favorites. Gear head guys love talking about cars all day long. Other guys may get a real kick out of explaining the technical aspects of their favorite sport to you.


You might learn how hands-on your guy is. If he likes to play sports or prefers to watch from the couch can tell you a lot about him, for example. Plus, you can learn what he feels passionate about and possibly come up with gift ideas for the future.

Have You Ever Cried in a Movie?

See if he’s a tough guy or a softy deep down inside using this question. Most guys tend to say no, even if the answer is yes, but a comfortable man isn’t afraid to admit the truth. Nearly everyone has cried at a movie at some point in their lives.

How Would You Celebrate Our First Anniversary?

In a new relationship, it’s crucial to get to know how your partner acts in a relationship. Ask your guy this question if you’ve been exclusive with each other for a while and want to see how romantic he is. The question may also help your boyfriend start thinking about what a long-term relationship with you may be like, as well as how he might want to spend your first anniversary.

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