33 Flirty Questions to Ask a Guy on a Date: The Proven Secrets To a Great Date

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Before you meet that next potential suitor, I want you to think about questions to ask a guy on a date.

Asking questions is a great way to get to know someone quickly, but asking the wrong questions can make him feel like you’re interrogating him.

Instead, I want you to focus on questions like the following as a way to develop the conversation on that date, not interview him as your next husband! In a moment, I’m going to go into different types of questions to ask a guy on a date, but first, let’s address why you need to even care about this.

Why It is Crucial To Know What Kind of Questions To Ask a Guy On a Date

woman with questions

Why do you need to have questions to ask a man on a date anyway?

Why do you even need to worry about what questions to ask a guy on a date? Why does it matter?

First of all, you don’t want to waste your time. If you and a man aren’t on the same page in terms of values or what you want out of life and love, there’s really no point in spending more time together.

Let’s say you love your hometown and see no reason why you should ever leave it. You’re on a date one night, and the subject of travel comes up. Your date tells you that in six months, he’s moving to Timbuktu. Isn’t that kinda important for you to know about a guy you’re considering dating and investing emotional energy into when clearly there’s no long-term potential??

Yea, a bit.

And another reason to think out what you want to bring up on a date: you want to avoid coming off as an interrogator…yet you want to read into what this guy is all about. The right questions (which we’ll cover here) will help you get insight into who this man is without making him feel like he’s being grilled.

Some of the following questions to ask a guy on a date work well on a first date, while some (like those pertaining to finances) you should save for the third or so date. After that, it gets easier to ask questions as you know him better and better. Let’s dive in.

Questions to Ask a Guy on a Date to Get to Know Him

Most people are nervous on their first date with someone new. You may be at a loss for what to say. Having some questions in your back pocket can make for icebreakers that warm up the date and help you get to know the guy you’re with. These aren’t your typical have you ever been married questions, and that’s a good thing. Your goal here is to ask open-ended questions that invite him to start a conversation without freaking him out. Try questions like:

  • Who has been the biggest influence in your life?
  • If you could live anywhere in the world, where would it be?
  • What makes you laugh?
  • What are you passionate about?
  • What are your three favorite things in the world?
  • Where are you from originally?

How these questions help you figure out compatibility: Like I said earlier: you want to know what a man is all about without giving him the third degree. Questions about what makes him tick and his experiences can actually tell you a lot about his personality. Does he eagerly answer your thought-provoking questions, or just shrug his shoulders and say I dunno? The first one is a guy you want to continue to get to know. The second? Well, be honest: do you really see potential there?

Questions to Ask a Guy on a Date to Learn About His Family

family values

Asking about his family can give you insight into the type of person he is.

Family values are important for most of us when we’re looking for a life partner. Is he close to his family? Does he have a similar upbringing to you? Or one that’s completely opposite?

Usually, asking someone about their family is a great way to get them to open up (unless there’s some tragedy or drama there. Still, if that comes up, it could be a red flag for you to pay attention to.). Even if he’s just telling stories about wrestling with his brother as kids, you can still glean information about who he is as a man.

Here are a few questions to ask a guy on a date about his family:

  • What was your family like growing up?
  • Does your family live here or somewhere else?
  • Who in your family are you closest to?
  • What is a tradition your family had when you were a kid?
  • Do you have any siblings?
  • Are you more like your dad or mom?

How these questions help you figure out compatibility: From my experience working with women, most of you feel safe when a man has solid family values. Am I right?? Knowing he was raised by strict parents and admitting that now he appreciates how he was raised can go a long way toward telling you that he’s probably a good guy.

Funny Questions to Ask a Guy on a Date

Laughter is a great icebreaker on a first date, especially if you or he are nervous. So even if you don’t know what to talk about, asking a funny question like the ones below can ease the tension and get him to open up to you.

  • If you could get away with anything without getting in trouble, what would you do?
  • What’s the most embarrassing thing you ever did?
  • Do you have a weird nickname?
  • What are three words that others would use to describe you?
  • What’s your biggest pet peeve?
  • Do you have any unusual phobias?
  • Who’s your celebrity crush?
  • In a movie about your life, who would play you?

How these questions help you figure out compatibility: You want a man with a sense of humor, don’t you? These questions aren’t what he’s expecting, so you’re likely to catch him off guard and see his true self.

Questions to Ask a Guy on a Date to Find Out What He Likes

Often the easiest place to start in terms of questions to ask a guy on a date is what he’s into. Sports? Hobbies? Talents? Getting him to talk about himself should be easy (we all like to talk about ourselves, both men and women), and hopefully, he’ll reciprocate by asking what you like.

Here’s something to chew on: while it’s nice when you have common interests with a man, eHarmony research shows that in the long term, compatibility isn’t really based on the superficial things you have in common. Still, in the early days of getting to know someone, learning about what he’s interested in can help you determine if you want to continue to spend time together. If he’s hard-core heavy metal and you’re smooth jazz, you might not be meant for one another.

Here are some questions to help:

  • What’s your favorite movie of all time?
  • What’s the last book you read?
  • If you could only eat one food for the rest of your life, what would it be?
  • Are you a cat or a dog person?
  • What type of music do you like?
  • What TV show are you currently bingeing?
  • What’s your favorite holiday?

How these questions help you figure out compatibility: Getting to know a man requires a million little data points. It may seem trite to ask him if he’s a dog or cat person, but it could open the door to a heartwarming story about his first dog, Pete. Talking about books can help you find out if he’s intelligent and thirsty for knowledge. Don’t underestimate the power of questions about his interests!

Flirty Questions to Ask a Guy on a Date

So you know you’re into this man…now you want to get a little flirty. Turn the conversation playful to let him know you’re interested with questions like these:

  • What was the best kiss you ever had?
  • How does a girl know you’re interested in her?
  • Do you kiss on a first date?
  • How’s this date going so far, in your opinion?

How these questions help you figure out compatibility: If he’s into you too, these questions will reveal it. They’ll also get him to open up just a little more.

Questions to Ask a Guy on a Date About His Ideal Partner

happy couple

Knowing what he’s looking for helps you figure out if you’re compatible.

Here’s where the questions get even more helpful in giving you insight into long-term relationship potential with a guy.  If, for example, he’s just looking for an FWB (friend with benefits) and you want a boyfriend, you can quickly find this out before you waste more time with someone who isn’t compatible for what you need in your life right now.

Keep in mind: these questions might be too personal to ask a guy on a first date, so save them for phone calls after that first date, or on a later date. But feel out the situation! This is murky territory for men, talking about relationships, so if you feel him pulling away after one question, don’t continue with more.

  • What are you looking for right now?
  • How long was your longest relationship?
  • What do you find most attractive in a potential partner?
  • What is your ideal relationship like?
  • Do you have/want kids?

How these questions help you figure out compatibility: When you’re considering the possibility of a relationship with a guy, knowing about his past is hugely indicative of where he’s headed. If he’s never had a relationship longer than three months, do you really think that you’ll be the one to break that chain? If he hems and haws about what he’s looking for relationship-wise, he’s probably not looking for long-term.

Questions to Ask a Guy on a Date About His Goals

We all want a partner who has goals and constantly works toward bettering themselves (well, I do, anyway). Maybe you’ve gone on a date with a dude whose only goal in life was to catch a wave or beat level 500 in his favorite video game.

But you’re better than that. You want a man who thinks about the future and makes an effort to achieve his dreams. And finding out what his goals are now can lay the groundwork for a relationship if that’s where this is heading. Couples who support one another’s goals tend to be happier and stay together longer. Sounds pretty good to me.

Here are some sample questions to ask a guy on a date to see how far into the future he’s thinking:

  • What’s your biggest goal right now?
  • Where do you see yourself in five years?
  • What’s a New Year’s resolution you made this year?
  • What’s on your bucket list?

How these questions help you figure out compatibility: Because you’re an accomplished and confident woman, you want a man who has goals, even if they’re different from your own. You want some sense that he has direction and purpose in his life.

Questions to Ask a Guy on a Date About His Career and Finances

man and finances

There’s nothing sexier than a financially stable man!

This is another tricky area to tackle when asking a guy about himself. Some guys are happy to talk about what they do and even their financial situation, while others are squirrelly about it. A female friend of mine asked a man she knew if all men disliked talking about their jobs, and he replied, only if they have crappy jobs.

So if he’s unwilling to tell you what he does for a living, he might be a little embarrassed about it. Typically doctors, lawyers, firemen, whatever, are happy to tell you what they do!

And questions about money shouldn’t come off as too nosy. Asking him how much he makes may be over the top. Still, you can use these questions as a means to find out if he’s financially stable or not.

  • Are you saving up for anything special, like a house or major trip?
  • Do you like what you do?
  • What’s your favorite thing about your job?
  • What does a typical day at work look like?
  • Are you a spender or saver?

How these questions help you figure out compatibility: Of course you’re not looking for a man to take care of you financially, but you do want a sense that he’s secure and isn’t looking for you to take care of him! Also, I think it’s really sexy when someone loves what they do workwise. You don’t want to date a guy who’s going to bitch about his job day in and day out, do you?

A Great Conversation Requires a Great Listener

With all these questions to ask a guy on a date, you should be covered for topics for your first five dates or more! The idea is that as you ask questions and he answers them (and asks his own in return), you start to know each other better and build a foundation to grow from.

But as important as the questions you ask is how well you listen. According to Amy Torres, a psychotherapist, there is a difference between hearing and listening:

Hearing what is said takes short-term memory — it only indicates that on a surface level you took in their words but didn’t join emotionally with the person speaking to you. Listening is being receptive to your own inner wisdom, while emotionally attuned to the other person.

So if the entire time he’s talking about his family history (because you asked) you’re thinking I hope he asks a question next. I could tell him that funny story about falling out of the tree, then you’re not really listening. 

Focus on what he’s saying. Repeat what he says from time to time, and ask followup questions:

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You: Where were you born?

Him: I was born in Detroit, but my family moved to Scranton a few months later. So I grew up in Pennsylvania.

You: Pennsylvania, huh? I’ve never been there. What’s it like?

Him: Really beautiful, actually. Especially in winter. I loved skiing as a kid.

You: Wow, I didn’t learn to ski until I was an adult. Were you any good? Do you still ski?

Give him the courtesy you would want him to give you: your undivided attention. Don’t check your phone. Don’t look around the room to see who else is there. Don’t check the score on the tv in the bar you’re in. While he’s talking, make him the center of your universe, and hope that he reciprocates.


first date

Asking the right questions can lay a solid foundation for a relationship!

Keep in mind that a conversation isn’t simply you peppering him with questions.  Ask one, let him respond, then take a beat. Give him the chance to ask a question about the same topic…or you can comment on the topic. This article isn’t meant to be a comprehensive list of questions to ask on a first date! Rather, it’s a guide to helping you tune into the topics you want to bring up so that you can better get to know this man and determine whether he has long-term potential or not.

Beyond his answers to your questions, also pay attention to what his body is telling you. Body language is so important, especially when you’re first getting to know a guy. If, for example, you ask him about past relationships and he starts squirming or can’t look you in the eye, something’s up. You might not get to the bottom of it right then, but pay attention to that red flag and proceed with caution.

If you’re asking questions about his past, his career, or his finances and you notice him leaning away from you in his chair or his eyes looking elsewhere, he may feel like you’re being too invasive. Back off.  The last thing you want to do is scare off a perfectly good guy with your inquisitive nature!

If he’s genuinely interested in you and wants to get to know you, he should be willing to answer your questions…and he should come with plenty of his own. Getting to know someone takes time, but it also takes two willing participants who are okay with opening up to the other person.

I want to hear from you. What’s one good question to ask a guy on a date that you’ve found successful? Tell us in the comments below.

What do you think? Share your thoughts below...

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5 years ago

This article is so helpful. All the points are so important, beginning from asking questions about him, his family, his future everything was so well written. Thanks for sharing.

4 years ago

Thanks for sharing. You didn’t say much on flirty questions to ask

4 years ago


4 years ago

Thanks.It is cute.

3 years ago

Wow! amazing post.. Thanks for sharing!

2 years ago

Not enough sexual questions

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1 year ago

Great post. I like how each question is making it where the guy has to think about his answer, and it is not just a yes or no type of question. Asking questions is important but it can be fun too.

Deborah Cosby
1 year ago

Im a 64 yr old widow I like a man who is 70
he lives in Newport and I live in Yorba Linda
We both have successful businesses
I own a preschool and he owns a real estate company
I saw him once and really liked him
H does not know of me at all
I don’t know how to approach him
I just have this feeling about him
How can I get him to go on a date?

1 year ago

Thanks for the post it was very informative. Order online medicine safely with assured next-day delivery in UK from UK top pharmacy store. Buy Now!

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