42 Questions To Ask a Guy

For centuries, the brightest scientists and most brilliant scholars have been stumped by one question. It’s baffled the greatest minds since the beginning of time. It’s a simple question. What are guys thinking? Wives and girlfriends often ask that question. Well, it turns out it’s not such a simple answer. Indeed, there are several questions to ask a guy. Indeed, men are more complex than women realize. 

Many men feel they must bottle up their feelings, but in truth, most are more than willing to open up. It’s a matter of asking the right questions. If women play their cards right, they could get answers about relationships, family, fears, life, and dreams. They could find out a boyfriend’s darkest secrets, their most embarrassing moment, and how they truly feel about them. They just have to know which questions to ask a guy.

1. What Are You Looking for in a Relationship? 

romantic couple sitting on a beach

It’s scary to ask relationship questions, but it’s a crucial topic to discuss. Sometimes, it’s best to be straightforward. Knowing if a guy is looking for something serious or just a fling is important. They might want to be in a committed relationship and want something long-term. Of course, it’s also possible they just want to be friends. 

2. What Are Your Flirting Techniques? 

couple facing each other

Most men spend years perfecting their flirting techniques and pick-up lines. Get a guy talking about his flirting techniques, and he might start showing off. It’s one of the best questions to ask a guy. It’s a smart way to see him in action too.

3. Have You Ever Cried During a Movie?

loving couple having coffee in the restaurant

Here’s a question that’ll help a guy open up. Boyfriends might not want to admit it, but they’ve all cried during a movie. It’s just a part of life. If they deny it, throw on a classic guy cry movie like Rocky, Good Will Hunting, or Brian’s Song. The tears will start flowing. It’ll help make him feel comfortable expressing his feelings. There are a lot of good questions to ask a guy, but this one’s vital. 

4. What Does Friendship Mean To You

couple talking seriously at home

Every guy has a group of friends, pals, and bros. It’s always good to find out about his friendship. His friendship with a close guy friend is a window into another side of his personality. However, knowing his deep thoughts on friendship also relates to his feelings about romantic relationships. 

5. Who Was Your First Celebrity Crush?

couple chatting each other in the coffee shop

The first crush is one of the most exciting times in a boy’s life, especially if it’s a world-famous celebrity. Every boy has a celeb crush at some point in their life. Most men probably still have a celebrity crush. It’s one of the fun questions to ask a guy. In some cases, it’ll be a good laugh, or it’ll reveal his “type.” 

6. What Frightens You?


It’s an interesting question that’s fun but reveals more about their personality and vulnerabilities. Every guy knows there’s no shame in being scared. There is always that scariest thing that frightens the bejesus out of them. Perhaps they’re afraid of the dark, heights, bees, or spirits haunting a mansion. Having said that, men are afraid of nothing. Well, maybe, ghosts.

7. Do You Like It When the Girl Makes the First Move?

couple staring at each other outdoor

This is a good question for a first date or dating app. It’ll help break the ice and is a good conversation starter. Indeed, many men love it when the woman makes the first move. It takes the pressure off the guy, which can be enormous. However, other guys might have a game plan and prefer to make the first move. 

8. What Is the Perfect Date? 

couple dating tip

Asking about the perfect date is a great question to ask a guy. Some boyfriends probably put a lot of thought into a date. They might make grand romantic gestures and spend a week’s salary. Of course, other guys might be more subtle and just do dinner and a movie. Either way, it moves the conversation towards a romantic relationship. 

9. Are You a Cat or Dog Person?

Laughing Couple With Dog

If any question can make or break a relationship, it’s this one. The wrong answer can throw a potential relationship into a tailspin. The right answer could move the romantic relationship forward. The animal he chooses could be a reflection of his personality. Some people love cats, and others go for dogs. Of course, some don’t like pets at all. But that’s a whole other conversation. 

10. What Is Your Guilty Pleasure Netflix Show?

watch a concert to experience with your partner

Sometimes, guys just want to stay home and watch their favorite Netflix show. However, every guy also has the one guilty pleasure show that embarrasses them. They might claim they were watching Stranger Things, but it was really Selling Sunset. It’s a great conversation starter that’s good for a laugh. It also sets up a chance to watch some Netflix and guilty pleasures. 

11. What Is Your Favorite Joke?


Having a sense of humor is an important personality trait for most people. Finding out his favorite joke is a fun question to ask a guy. It’s a good indicator of the type of humor they enjoy. They might love puns, silly jokes, parody songs, or dirty humor. It’s an easy way to relate to a guy and find out about his favorite comedies as well. It’s also another way to set up dates too.

12. What Is the Best Part of Your Job?

couple smiling while using laptop

A personal question about a guy’s job is a great way to start a conversation. Work is a big part of everyone’s life, even if they hate it. Asking about his job shows interest in what he does for a living. Of course, it also impacts any plans you want to make for the future. Every guy has something about the job they love the most. It’s fun to learn more about his interests and hobbies as well. 

13. Who Would You Want To Play You in a Movie?


Every guy has thought about which famous actor he wants to play him in a movie. Pay close attention to the person he chooses. It’ll reveal if they have an ego or are really humble. For instance, if the guy goes straight to Dwayne Johnson, they might think highly of themselves. It does become an exciting question when casting the girlfriend’s role. Regardless, it’s an interesting question that might lead to some deep conversations. 

14. Where Do You See Yourself in 5 Years?

play truth or dare to experience with your partner

When entering a serious relationship, it’s essential to know if there’s a future. It’s fair to ask a guy questions about his plans. Perhaps the guy sees himself getting married, traveling, or sitting in his pajamas playing his Xbox in five years. It’s impossible to predict the future, but it’s always good to have a plan.

15. What Superpower Would You Want?

happy couple dating image

It’s another fun question to ask a guy. Honestly, he’s probably been waiting years for someone to ask. Men often think about the person they want to marry, the type of job they want, and most importantly, what superpower they want. A lot of guys would say being invisible or flying. An intelligent man would say unlimited endurance or controlling time.

16. What Is Your Best Pick-Up Line?

happy young couple dating

Dating in 2022 is nothing like 1982. It’s common now for soulmates to meet online. Of course, dating apps have their obstacles as well. Asking about the best pick-up lines is a great conversation starter. It’s a fun question that’ll turn the conversations a little flirty. The best pick-up lines range from subtle to very creative. 

17. If You Could Time Travel To Any Historical Period, Which Would You Choose?


Most guys spend hours thinking about time travel. They think of a million places they would travel to in time. If time travel were real, it would be a great idea for a date. There are incredible moments in history that would be worth checking out. He might take his date to a romantic historical moment or watch a classic performance. It’s another great question to ask a guy.

18. What Is Your Dream Job?

beautiful couple talking

Careers are a big part of everyone’s daily life. Indeed, many people’s lives revolve around their job. A few lucky people get their dream job, but not everyone. Guys love to talk about their dreams and goals. Discussing dreams and goals is a great way to learn more about him. 

19. What Is Your Favorite Food?

happy love couple

Asking about food choices has a dual purpose. First, food is always an easy subject to discuss. Second, this helps set up future dinner dates and outings. It’ll also help to find out about allergies as well. It might seem like a random question but asking about food is the way to a man’s heart. 

20. What Is Your Dream Vacation Spot?

couple drinking coffee outdoors

Discussing dream vacation spots also serves two goals at one time. First, it’s a great conversation starter. Also, it’ll set up future vacation plans. He may want to travel through Europe, relax in Hawaii, or party in Las Vegas. Maybe even all three places. It’ll reveal a lot about his personality as well.

21. What Is Your Favorite Song?

couple listening music together

Another perfect question to ask a guy is about music. Sometimes, asking a simple question is the easiest way to make someone feel more comfortable. However, the types of music a guy listens to show his deeper side. It’s also wise to make sure they have good taste in music. 

22. What Is Your Most Embarrassing Moment? 

couple enjoying coffee

Everyone has that embarrassing thing that they wish they could forget. However, it’s not the worst thing to ask. Indeed, they’ll feel more comfortable opening up, especially if there’s no judgment. It’ll probably be a funny story and help the relationship grow closer. 

23. What Is the Craziest Thing You Have Ever Done?

couple talking laughing

Finding out the craziest thing a guy ever did can be very eye-opening. Perhaps they did something adventurous, like skydiving, bungee jumping, or running with the bulls. Maybe they eloped in Vegas, started a riot, or committed a crime. Perhaps they never did anything crazy and are looking for someone to bring it out of them. 

24. What Is the Last Thing You Would Do If the World Were Ending in 24 Hours?

couple having take away coffee

If the world was ending in 24 hours, what’s the last thing you do? It might seem like a silly or random question, but it’s much more than that. It’ll reveal a guy’s priorities. Perhaps, he wants to take in one last sunset with the love of his life. However, he might want to play Call of Duty with the boys one final time. 

25. What Is Your Favorite Thing To Do on Weekends? 

go camping to experience with your partner

It’s important to ask a guy questions without revealing your real intention. For instance, ask him his favorite thing to do on weekends. It’ll show how he spends his free time. Maybe he spends it visiting his parents, working on his car, or watching TV. At the same time, it helps set up weekend plans for the future. 

26. What Is Your Family Like and Do You Have Any Siblings? 

take on a puzzle to experience with your partner

Finding out about a guy’s family is a window into his personality. It’s a way to ask questions about his childhood, family life, and current relationship with his parents. His relationship with his siblings is a way to know more about him and get closer to his family. It’s a good conversation starter and a way to ease into more personal questions. 

27. Do You Believe in Soulmates? 

How To Deal With a Jealous Partner

Here’s an excellent romantic question to ask a guy. Discussing soulmates is a way to get closer and connect on a higher level. Of course, it could always turn into a disaster. Many men hide behind a tough guy persona, but they’re really romantics who believe in soulmates. 

28. What Is Your Favorite Ice Cream Flavor? 

coupole laughing together dating outdoor

It might seem like a random question, but ice cream flavors tell a lot about a guy. Plus, it’s delicious. Men and women are similar to ice cream flavors. There are millions of different ones. Of course, choose wisely because you don’t want a stomach ache. Asking about favorite desserts sets up future dates and is the perfect question to ask a guy unless he’s lactose intolerant.

29. What Is Your Favorite Movie?


Talking about a guy’s favorite movies is the best way to learn about his interests and hobbies. More importantly, it sets up potential movie dates. There are several types of movie dates, including going to a theatre, the drive-in, or staying home. Regardless, they’re all fantastic options. It’s a good question for either person to ask. 

30. What Is the Best Gift You Have Ever Received? 


It’s a simple question that’ll prompt a loaded answer. Every guy has received a gift at some point in their life. Knowing about a meaningful gift will show what he values and holds near his heart. It’s also a great way to come up with potential gift ideas. 

31. What Is the One Thing You Would Change About Yourself? 


This is an excellent question to see a guy’s vulnerable side and check for any red flags. For instance, it’s a pretty big red flag if he wouldn’t change a thing. Guys are like all humans and constantly find imperfections. They might want to alter a physical trait, emotional issue, or a life change. 

32. Do You Want To Have Children Someday?

take risks to become a dominate partner in a relationship

A healthy relationship starts with both people putting their cards on the table. Finding out about a guy’s future plans is good for the relationship. One of the most crucial questions is about having children. Some boyfriends are eager to get married and start having babies immediately. That rule doesn’t apply to every guy. He might not have the same goals, which is fine. It’s best to find this out as soon as possible. 

33. What Makes You Smile?

Always Ask Open-Ended Questions To Know Your Partner on a Deeper Level

Asking a man what makes him smile is one of the simplest questions to put to a guy. It allows him to openly admit something he might not do to someone else. Perhaps a beautiful sunny day makes him smile or a cute puppy video. Of course, a wise man would answer that the person asking him the question is what makes him smile. 

34. Do You Believe in Love at First Sight?



Some guys are into romance, and others just want to go to bed. However, asking a direct question about love at first sight, reveals his feelings on relationships. It’s a simple way to discover a guy’s romantic side. Maybe they’ll want to wine and dine on a date or make you pay for your own happy meal. There’s no point in wasting time. It’s a question that seems superficial but can turn into a deep conversation. 

35. How Would You Survive a Zombie Attack?

Avoid Calling Them Names When Dealing With Possessive Partner


The most important question a woman should ask a guy on a first date is how he’d survive a zombie apocalypse. It’s one of the essential questions to ask a guy. Guys must have their priorities straight. Some men might want to hunt zombies, but searching for food is vital. It’s also possible that some would run and hide. It reveals crucial truths about a guy’s feelings about his date and zombies. 

36. Is Jealousy Healthy in a Relationship? 

couple talking while in a bed

Believe it or not, a relationship has an acceptable amount of jealousy. A tiny bit shows how much a person cares. Of course, too much jealousy is a bad thing. It’s not a random question and is a fair topic to discuss. Being more open and honest is suitable for both guys and gals. 

37. What Is the Meaning of Life?


Asking a guy a question like this is a bit tricky. It can be a simple question that leads nowhere or to a disappointing answer. However, if the conversation is already at a deep level, this is the perfect question to ask a guy. It’ll give great insight into a guy’s thoughts and feelings on relationships. Perhaps, getting married and having kids is the true meaning of life to him. On the other hand, the meaning of life might be playing video games.

38. Have Your Eyes Lost Someone Close To You?

Try the Compliment Sandwich To Make You a Better Partner


Losing someone close is tough for any person to go through. It might feel uncomfortable, but it’s a fair personal question. Some guys might have a tough time talking about something so painful. Therefore, asking the question makes it easier to open up. Getting more personal helps bring the relationship closer.

39. What Is the Most Embarrassing Thing in Your Search History? 


There’s one simple way to watch a guy panic and his face turn red. Ask him what’s the most embarrassing thing in his search history. Most men are terrified to answer that question. Maybe they were looking up naughty videos or searching the results of last night’s episode of The Bachelor. Regardless, there might be a few funny answers for a good laugh.

40. Your First Time?

Always Ask Open-Ended Questions To Know Your Partner on a Deeper Level

Everyone remembers their first time no matter how much they try to forget. Finding out about a guy’s first time is fun but a personal question. He might still have fond memories or has a funny story to tell. It’s probably a short story but funny nonetheless. It’s an intimate question that’ll lead to a deep conversation. 

41. What Is Your Dirtiest Fantasy?


A flirty question is a great question to ask a guy. First of all, guys love when girls flirt. However, it’s also a revealing question that’ll tell you more about their emotions, fantasies, and kinky side. Plus, dirty questions can lead to all sorts of fun places. A popular response most guys give is role-playing. Depending on their age, they’ll say Princess Leia in a gold bikini, C.J. Parker running down the beach, or Harley Quinn with a bat.

42. What Does It Mean To Say “I Love You?”

woman smiling while looking at his man

Saying “I love you” is a big moment for any relationship. However, the conversation about the phrase shouldn’t come too early. It’s a fair question to ask a guy and gives great insight. Some guys might have said it in the past and not meant it. It’s also possible the question will lead to a discussion about a past relationship. It’s one of the biggest questions to ask a guy.