In this article, I've listed the best questions to ask a guy on a date.

A great conversation topic can always spark a budding romance which is why I've written a lot of articles teaching women how to start a conversation with a guy and come up with the right questions to ask in all sorts of dating situations. I have been published on sites like Bustle and Best Life Online so you can trust me to guide you on your date.

These questions to ask a guy on a date are flirty in a good way and never short of interesting. If you want to score a second date, keep reading.


Ultimate List Of Questions To Ask A Guy On A Date

A successful first date will never be without an interesting conversation, and an interesting conversation always starts with a great question. This list of questions to ask a guy on a date will make you and your man laugh, ponder, and fall closer together.

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4 Best Questions To Ask A Guy On A First Date

A first date is always a great opportunity to get to know a guy and figure out whether or not you'd like to go out with him on a second date. These interesting questions always reveal a man's character.

1. What makes you unique?

Each person has a unique life story that sets them apart from everyone, and these life stories, although different from one other, all connect us in a way. Isn't it amazing how fate has a weird way of bringing two people together?

2. What’s one thing that defines who you are?

Maybe his zest for life is the best of him. Perhaps it's his creativity. We all have that one defining trait that people will always remember us for. Maybe for you, it's his kindness.

3. What's something you're proud of?

We all remember our big moments- from buying our first car to landing our dream job. Don't you just love a man with big dreams?

4. What is the best compliment you’ve ever received?

Guys love compliments too, you know? A great follow-up question would be, "has anyone ever told you how sexy your laugh is?" or any similar question in that line. The idea is to catch him off guard with a flirty compliment.

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5 Random Topics To Ask A Guy You Just Met (Blind Date)

A blind date can be nerve-racking, but it can also be fun. The key is to embrace uncertainty and enjoy every moment as it is. No expectations, just two people getting to know each other. These random questions to ask a guy are perfect for blind dates.

5. Do you hate small talk?

Asking this question is a good way to gauge how well a guy carries a conversation. An extrovert will not have a hard time answering this question, but an introvert might take a while to explain himself.

6. What's your favorite thing to do in the morning?

I love a good run in the morning. Maybe your guy enjoys making breakfast. If he's a morning person, he won't have a hard time answering this question.

7. What kind of music do you like and which places in the city do you want to go to?

Did you know that sharing music is an effective way to bond with someone? When we share music, our body releases a hormone called oxytocin, also known as the love hormone. It's the hormone that makes us fall in love.

8. Is physical appearance the most important?

Attractiveness is one thing, but a person's character, beliefs, ideas, stories, and experiences are what make them beautiful.

9. Would you make breakfast in bed for a girl you fancy?

Call me high maintenance, but the only good answer to this random question is yes or "I can try" because when a guy is genuinely attracted to you, trust me, he will try.

5 Fun Date Questions To Break The Ice

Dates should always be fun. How about asking some light questions to take the edge off? These fun questions to ask a guy are perfect for casual dates over a beer or a café latte.

10. Nice Car or Nice Home Interior?

There is no wrong answer. A nice car could take you places, and having a nice house to come home to is more than welcome.

11. What type of food do you like?

Bonding over food is also a great way to connect with people. If your first date worked out smoothly, you might get to cook him his favorite food.

12. What is the first thing you'd do with your money if you won the lottery?

Now this one's a fun question. If you have mad money, imagine what you could do with it. I'll probably buy an island, learn how to farm, abandon the city, and live as a rich hippie.

13. What was the worst date experience you have had so far?

If you're lucky, the worst thing that could happen to you is to get blown off. I've tried online dating, and some people there are just weird.

14. If you could change your name, what would you make it and why?

A flirty comeback could be, "can I make a suggestion? How about I call you baby?"

5 Interesting Date Questions To Ask A Man To Know Him Better

Okay. Enough with the flirty question. How about asking some deep questions to help you get to know your guy just a little bit better? Don't know what kind of topics to ask a man to know more about him? These interesting questions to ask a guy never fail to break the ice.

15. Do you think it is possible that your best friend and your spouse could be the same person?

You'd be living your best life if you had a best friend and lover in one person. Sharing and enjoying things together is important if you want a healthy relationship with your partner. It's really not that hard when you love someone.

16. What is one thing that brings a smile to your face, no matter the time of day?

A funny cat video can always make my day. How about starting a habit of surprising him with his favorite thing at random times of the day? You know. Just because.

17. Would you take the advice of a relationship expert?

If you have nothing to lose, why not? A relationship expert is an expert for a reason. You could be missing out on a piece of advice that could get you a Taylor Swift love story. Who knows.

18. What’s one thing people would never know about you just by looking at you?

Asking this deep question might surprise you. It's true what they say- it's hard to judge a book by its cover.

19. What’s your zodiac sign? And do you think it describes you?

He's probably not as familiar with astrology as you are, so you might have to describe his sign for him. At least now you know if your signs are compatible.

5 Personal Topics To Ask A Guy To Start A Deep Conversation

These deep questions to ask a guy will help you fall in love.

Did you know that asking increasingly intimate personal questions is a great way to accelerate attraction between two people? According to psychologist Dr. Arthur Aron, asking personal dating questions builds intimacy by gradually establishing trust as each person reveals something private about themselves.

20. Who or what is your biggest go-to person or activity when you're feeling down?

Spending time with the people you love or doing an activity you enjoy is a great way to take care of your mental health on days when you're not feeling great yourself. For me, it's taking a break from social media and taking a quiet walk in the park.

21. What is one thing that you’re thankful for?

Practicing gratitude is also a good way to improve your mental health. Listing down at least 5 things you're grateful for the day can help improve your mood and overall outlook in life.

 22. What is better, in your opinion: asking for forgiveness or permission?

Why don't we practice doing both? Learning how to ask for forgiveness or permission will save you a lot of time arguing with someone you love.

23. Have you ever made a decision that changed your entire life? If so, what was it?

What's the craziest thing that happened to you that completely changed your life? This is a good question to ask a guy if you want to learn more about his life.

24. What is more important to you: money or happiness? Why?

I mean, money can buy things that make me happy? Perhaps if we didn't live in a capitalist economy, I'd choose happiness but having a lot of money isn't so bad either.

Downloadable and Printable List of Romantic Questions to Ask a Guy on a Date

Here is a downloadable and printable jpg/pdf list of romantic questions to ask a guy on a date (right-click the image and select Save Image As...):

The No.1 Thing You Must NOT Do During A Date With A Guy (From A Female Perspective)

Like I said, first dates should be fun, and you shouldn't be putting too much pressure on them. The last thing you want to happen is to get too attached to a guy too soon. A first date isn't the be-all and end-all of an awesome relationship so relax, have a good time, and trust the process.

Besides, if you're nervous about it, it will show and will affect your confidence. You need to live and enjoy the moment while it lasts. If it works, great. If it doesn't, thank you, next.

How To Ensure That The Questions Are Not Turning Him Off

A date is always a great way to get to know someone, but it's not supposed to be a hot seat for anyone. You don't want to be anyone's first date horror story, so unless you want to be some guy's cautionary tale, take a chill pill and go easy with your questions.

1. Before Asking a Question, Do a Reverse Uno Card in Your Mind.

When you're trying to come up with a good question to ask a guy, the rule of thumb is if you feel uncomfortable answering a question, it would probably be the same for the other person.

For one, you might want to reserve the dirty questions for your fifth or sixth date. I mean, guys love women they can be naughty with, and who can turn them on, but your first or second date is too early of a time to start throwing questions like, "what's your favorite sex position?". Besides, when you ask questions like that, you're putting the poor guy in a tough spot when you aren't even sure he likes you well enough.

The same goes for asking serious relationship questions like, "where do you see this relationship going?" or "do you want to have kids?". That's too much too soon and should be avoided if you don't want a guy to ghost you or never call you again.

2. Don’t Pepper Him With Questions

Asking too many questions is as worse as asking bad ones. According to sociolinguistic Deborah Tannen, women use conversation to establish connections, emphasizing "similarities and matching experiences."

During a first date, a woman will instinctively try to find connections that can reduce her uncertainty about a potential partner. This means you're more inclined to ask more questions to determine whether the man across the table is a potential match.

Slowly reducing uncertainty about another person through disclosures is a "key to the advancement of any relationship," said Anita Vangelisti, a University of Texas professor and expert on interpersonal communication between romantic partners.

While this is a good strategy, the problem is that some women will try too hard to fish for as much information as possible and end up peppering their date with questions as if they were FBI interrogators.

Frequently Asked Questions

Here are frequently asked questions to give you some more pointers for your first big date.

Do guys like being asked?

Of course! Men always enjoy the company of a woman who can ask interesting questions and hold meaningful conversations. What men don't like are women who pry on their lives so avoid asking questions like, "you seem great. Why are you still single?" or "are you seeing anyone else?".

Before you go on your first date, practice how to start a conversation with a guy - probably with a friend who has had a lot of experience dating men.

How do I know if he's worth dating?

That depends on you, which is why you need to have your negotiables and non-negotiables figured out before jumping into a relationship. This means you need to know the qualities and traits you'd want in a man, so you can easily put the finger on whether or not he's worth dating based on your standards.

Is kissing on a first date a good or bad idea?

One of the most important first date tips I tell women is to reserve their first kiss with any man after their fifth or sixth date. A kiss will put your relationship on another level, and you want to make sure you're not rushing in too soon. Consider it as your seal of approval and let a man work for it.

How can I tell if he's interested in a serious relationship?

Many women ask me how to tell if a guy likes youIt's simple. One word- reciprocity. A guy who genuinely likes you will put in the same amount of effort as you in all stages of your relationship.

If he goes out of his way to make plans for dates or spend some time to get to know you, whether it's replying to your texts or going to a pottery class with you because he knows you like it, that's a green flag.

More Awesome Article To Explore

Our words are powerful and can make or break a relationship so make sure you're only saying good stuff. Here are some more articles to help you out.

  1. If your man's love language is words of affirmation, these romantic things to say to your boyfriend will melt his heart.
  2. Online dating? Here are some text conversation starters to get the ball rolling.
  3. Knowing a few date questions is great, but there are many more meaningful things you can talk about with a guy. Don't know what to talk about with a guy? I got you covered.

In Conclusion

And that is it on this list of the best questions to ask a guy on a date.

Knowing the right questions to ask makes all the difference between a memorable date and a bad one. Now that you know how to start a conversation with a guy making a connection with your date will be as easy as pie, and remember to keep it fun.

This list of interesting questions to ask a guy on a date has never failed me, so I have high hopes for you. Good luck out there!