47 Powerful Open-Ended Questions to Ask a Girl on a First Date

Open ended questions to ask a girl on a first date


You have a date planned!

On your date, you can reap the benefits of all your hard work.

We don’t assume that you got here after a date that ended badly.

Preparation is key.

That’s why we will give you the best tips and lines…

What you will learn in this blog:

  • 47 top open-ended questions to ask a girl on a first date
  • Which date questions you should ask and when according to the Date Rhythm,
  • Which first date questions to avoid a kamikaze date
  • How to have a good flow in your date conversations with a girl
  • Best top questions that make her slide of her chair giggling

Starting now, do you only want to have amazing flirty conversations that will ensure she will like you? Download my Boring Conversation Killer Cheatsheet that will help you have the coolest conversations with women.

By the way, have you seen my free Transformation Kit?

You'll get my best stuff absolutely free: 12 Opening lines that actually work, my 5 best texting tips (including copy-paste lines for Tinder), and the Friendzone Houdini. Download the Transformation Kit here.

What to ask on a first date?

Before we dive into the top open-ended questions to ask a girl that will guarantee a smile on her face and an intrigued thinking-frown or a sparkle in her eyes, let’s go through a few notes first.

I know that a lot of men suck at dates. That is not my opinion, but the opinion of tons of women I spoke to.

“If you fail to plan, you are planning to fail”
Benjamin Franklin

The reason why not everybody prepares a list of questions for their date is that it stresses them out. It takes away the spontaneity.

Men think conversations should come naturally, because otherwise, they feel like losers. Moreover, if a conversation doesn’t flow naturally, that means that there is no connection.

The truth is, men that think that way are selling themselves short. Just like I did during my job applications in the past. I went from a year-long journey of vague internships and part-time jobs to a top-earning function with just a bit of practice. A task well begun is half done.

“Give me six hours to chop down a tree and I will spend the first four sharpening the axe”
– Abraham Lincoln

You can transform your dates this way too, to make sure they don’t end with a fizzle, but with a bang.

Okay, we now agree that EVERYBODY benefits from a good date preparation.

So, let me give you some more tips on how to best use this First Aid List of Questions for First Dates. The last thing you want it coming across as fake or robotic.

First date questions for Date Kamikaze

A kamikaze date is everything that resembles a formal job interview. Imagine questions like:


“What job do you have? Where did you go to college?”

The risk in asking these questions to a woman, especially when asking them too soon, is that it shows a lack of creativity. It suggests you are a sheep going along with the masses that mostly view people as professionals. Of course, the profession a person chose says a lot about them. But, at the same time, it also says a lot about you, giving the message that this is the primary way you look at people.

“What hobbies do you have? What do you do besides work?”

Be careful with very GENERAL questions. People are not triggered by these general issues. World peace, for example, is too big of a topic to discuss. But, talking about how to solve a conflict between neighbors could be an interesting discussion.

“How do you like this place? How is your food? How was your day?”

There is nothing wrong with these questions provided you ALTERNATE them with more IN-DEPTH and CREATIVE ones. Lots of couples in a rut don’t have any more things to ask each other than ‘How was your day?’ and this is the last thing you want to be associated with.

The last thing you want is a conversation that is too STRAIGHTFORWARD, a purely functional information exchange. I-am-a-robot-and-I-need-the-following-information-to-determine-if-you-are-a-suitable-robot-that-I-can-date (read in the voice of C-3PO from Star Wars).

“Dan… Sometimes I just don’t know what to ask and then I ask one of those questions. Is it really thát bad?”

Look, you want to distinguish yourself from the average guy on a first date. Top questions to ask a girl will help you with that. This is how you will get noticed by her and how she will think you are more intriguing.

When you do ask these interesting questions on your date, ask them slightly differently. Be the odd duck in the pond, but in a positive way ;).

For instance, add the word ‘exciting’ or ‘crazy’ to your question.

For example:

“Do you have any exciting hobbies?”

That one word makes a world of difference. You give a critical subtext to the question by asking specifically for something ‘exciting’. She will now have the feeling that she has to fulfill this requirement and it will make her think longer about her answer instead of giving you one of the thirteen-in-a-dozen answers.

Now, an important point about open-ended questions to ask a girl on a first date…

The Rhythm of good first date conversations

You don’t want the questions to come across as if you’ve memorized them. What you do want to do is spread your questions throughout the conversation. You want to hide them, so to speak, like you used to hide presents in the grab-bag at Christmas.

Cluster the questions. Ask a couple of questions from one category, before you smoothly move onto the next topic. Don’t let your questions jump all over the place but, also, don’t jump too little.

Feel out what the conversation needs. When the vibe gets a bit heavy from all the personal shit being shared, throw in something refreshing and light. This is the RHYTHM of a cool conversation.

Above all else, ask women questions that YOU find interesting, what YOU want to know about her. If you do this, you won’t have to worry about sounding sincere or not. Memorize the questions for which you really want to know the answers. She will appreciate this.

The rhythm or a date-pro conversation could look like this: small talk – funny – serious – funny – sensual – serious – deep – small talk – etc. It’s a dance, a cocktail, a constant shift of different emotions.

Pro Tip:

Do you have a first date planned with a beautiful woman soon?

Then I got good news for you.

I wrote an article specifically on what questions you should ask on a first date. Check it out here:

>> 47 Powerful Open-Ended Questions to Ask a Girl on a First Date

The right structure for great first date conversations

Besides all this, you have to keep in mind the right STRUCTURE of a sparkling conversation. This should have a cocktail of light, humor, deeper bonding, and sensuality.

It’s a good sign when you get to the more in-depth and vulnerable topics together.

Women only do that with people that have a special place in their life.

Some men have a style of communicating that focusses on deep and heavy topics.

This could work really well, but you have to be careful not to move too quickly. Getting to somebody’s core is like slowly peeling an onion, not chopping up an onion like a professional fruit ninja.

Every first meeting knows a cycle of phases, as will your date. It is up to you to guide the conversation in the right way.

The date rhythm can be roughly divided into the following phases:

  • Withdrawal phase
  • Exploration phase
  • Chill phase
  • Deepening phase
  • Completion phase

Even though there aren’t any hard rules for which questions are best to ask first, I set them out that way to give you a clearer idea of the STRUCTURE for brilliant date conversations.

By using these questions to ask a girl on the first date to your advantage, you won’t hear the words “That was nice, I’ll be in touch” coming from her mouth. That’ll be ancient history. So, free up some space in your schedule, because you will start seeing a lot more of your date from now on.

One little bro side-note:

Questions you ask are bound to come back to you.

Open-ended first date questions for the Withdrawal Phase

This is for the first ten minutes. You’re still waiting for your drinks, or you just met up and are walking towards the café.

What are the first questions to ask a girl?

Let’s go:

1. Do you always look this good? Are you always this charming?

This question is a confident compliment. This subtext is: I am confident enough to give you a good feeling. Key here is intonation. You should come across as surprised/enthusiastic. Giving. Not dull or degrading. Then, you can kiss your good ending goodbye.

2. What do you hate most about meeting someone for a first date?

This question acknowledges the situation you are both in: the first date. Asking this relieves some of the tension and show social intelligence.

3. What is the worst pickup line you’ve ever heard?

Similar to the last question. You touch on the subject of ‘dating’ and recognize the elephant in the room. Doing this makes the situation less charged.

4. What is the most awkward situation you’ve ever been in?

By bringing up ‘awkward experiences,’ you indirectly name something you both fear: that his date will be an awkward and painful experience. By cutting to the chase, you again relieve some of the tension. Besides that, awkward experiences are hilarious to discuss and put people at ease.

5. What is the most horrible date you’ve been on, and what did you do about it?

Same as before. By talking about other dates, you indirectly indicate that both of you have other options than just the person sitting before you. This has a freeing effect and shows that you think from abundance. One footnote for this question, though, make sure that you do better than her other dates. But, that should be a piece of cake if you’re familiar with our articles.

6. What was the last time you tried to look cool and failed?

The topic of ‘awkward’ always gives you the best stories. People don’t like hearing about how you won the lottery. But they do like hearing about the bad choices you made after winning the lottery.

7. Which nicknames do you have for your friends or colleagues?

By approaching the topic of nicknames, you enter the domain of intimate friends. It’s also a trigger for hilarious and revealing anecdotes.

8. Which conspiracy do you wish you’d invented? (Or would you like to invent)

Bringing up conspiracies makes the conversation much cornier. It could also create an air of conspiracy between you and her versus the rest of the world. You can continue the conversation to you and her forming your own conspiracy.

9. What do you hate without having a good reason?

People sometimes find it difficult to name what they like. But everybody can name the things they don’t like.

10. What do most people think about you that’s absolutely not true?

By asking this question, you will make her feel understood by you if this is an issue for her. You give her the chance to take away any falsehoods or assumptions you might have about her.

Now, these questions are great if your date likes to talk.

But what if you have a date with a shy girl? In that case, you might need to make an effort to keep the conversation flowing.

Read this article here

>> What Should I Say to a Girl – 17 Best ‘Tricks’ to Spark Awesome Conversations

Interesting questions for the Exploration Phase

The moment after your drinks have arrived, is always a crucial one, because the arrival of the drinks interrupts the flow of the conversation. This is also the moment when the date has officially begun. This is it. However, with these next 14 questions, you have nothing to worry about.

So, what open-ended questions can you throw into the mix now?

11. What is the most ridiculous rule you have for yourself?

This touches on obsessive behavior, which everybody does in some way. By mentioning this, you create a bit of a light and fun vibe because you both have to reveal some lesser qualities about yourself.

12. What are the nicknames that people have given you?

Now it gets even more direct, and you’re going to talk about nicknames for her. One of my nicknames in high school was XXX. Not the most flattering title, but sharing this is quite freeing ;).

13. Tell me about your friends, what kind of friends do you have?

This a serious and somewhat standard question. The trick is to ask it in an original way. The reason that it’s standard is because it works so well. “Tell me who your friends are, and I will tell you who you are.”

14. What do you think about chick flicks, and what is the last one you saw or read?

Chick flicks, typical women’s books, and movies are one of the biggest joys of women that make them giggle. Especially when men talk about them. The subtext here is that you are up-to-date on what is happening in the female scene. It says: I am experienced with women, and that’s a big plus.

15. If you could choose a superpower, what would it be?

Talking about superpowers takes her back to her childhood. We all know what it felt like to be a child: free, carefree, and a rich fantasy. These are good associations. Besides, her answer will tell you a lot about her, and you can probably keep talking about this for hours.

16. What is the last book you read?

Personally, I am an information junkie. That’s why I prefer girls who read over girls who watch television. For me, this a deciding question.

17. If she is from abroad: What part of your culture are you most proud of? And the least?

If your date is from another culture, this is a perfect subject for discussion. But be careful you don’t exploit the topic. For you, talking about her culture might be new, but for her, it isn’t.

18. What do you suck at?

Quite direct, but also funny. You’re asking her for some vulnerability, so be prepared to reveal something about yourself as well. The answer to these types of questions are perfect for running gags, jokes that you keep making to tease her with.

19. Which movie or book character are you most similar to?

By making her compare herself with a fictional character, you will bring her fantasy alive. Women sincerely appreciate bros that will succeed in doing this.

20. What typical guy-thing do you like?

By talking about typical guy-things, you emphasize both your roles. You are a man, and she is a woman. Hmm, what possibilities might this bring? 😉

21. How decisive are you?

It’s a typical girl-thing to seek out more approval and to be a bit less decisive. By talking about this, you emphasize her female role and energy.

22. Which meeting or friendship changed you the most?

This is a deep question. But, by linking it to friendship, it becomes more accessible. If she can give you a good answer to this question, it will lead to a serious strengthening of your connection.

23. What kind of cult would you start?

By talking about a ridiculous subject like cults, you can start up some role play. One of you can pretend to be the cult leader. Hmm, the things you could do as cult leader 😉

24. If you were put in an asylum without your permission, how would you convince the staff that you are not crazy and not just acting normal?

This question is also a playful challenge. You also indirectly suggest that you could picture her in an asylum, just to put it out there.


‘Ever heard of the Arthur Aron’s questionnaire?

It’s a list of 36 very powerful questions that can make someone fall in love with you (Science confirms!)

In this article, I share the questionnaire with you, divided into three sets of 12 engaging questions:

>> The 131 Least Boring Questions Ever to Ask Your Date

Chill Phase, Chill Questions

Ok, you have gotten to know each other a little bit. The tension has been lifted. Now, it’s time to get to know each other better in a more relaxed way. The next interesting questions to ask on a date will help you with this.

25. What is your current passion in life?

Now we got to the more chill phase. We can ask some more basic questions. By asking for her ‘current’ passion, you make it more specific and, therefore, more comfortable to answer as well.

26. What is the one job you could never do?

Here also applies: people have an easier time explaining what they don’t want than what they do want. You also raise the feeling of “Pff, I am happy not to be doing that…

27. How old were you when you fell in love for the first time?

By talking about this, you get to know her better when it comes to dating, love, and more. Besides, it will induce powerful feelings related to falling in love and boyfriends.

28. Which spot on your body is most sensitive to tickling?

Tickling? Did he really say: tickling?” Yep, I did. This question is an easy segue to start tickling her. “Oh, let me try ;)!”. This will then get you closer to a pillow fight if you catch my drift.

29. Who is your biggest role model?

Another classic. Again, because it teaches you so much about her.

30. What is your favorite family tradition?

By talking about mutual families, you create an atmosphere of being in a relationship. Whether that is your intention or not, bringing up this topic too quickly doesn’t work. At the same time, traditions can be a fun aspect of family life.

31. What are the best and worst parts of being a woman?

With this question, you also emphasize her femininity and your masculinity. Plus, you show, like before, that you feel comfortable in the female world. For her, this is very comforting and reassuring.

32. What do you think is hilarious, but others don’t think it is funny at all?

Every human has their own sense of humor. Bringing this to the forefront for and with her is a great gift. Even if this is incredibly nerdy humor.

33. What is the most creepy thing you could say to an innocent stranger on the street?

Of course, this is a completely ridiculous question. It’s the humor like in movies such as Scary Movie. The advantage is that, if you come up with good suggestions, you can keep bringing back this topic when meandering about on the streets.

34. What do you like least about your appearance?

Even if she looks like a professional model, everybody can name their imperfections perfectly. Also, by bringing this up, you imply that you aren’t totally impressed with her mesmerizing looks.

35. What is the weirdest conversation you ever eavesdropped on?

This question might come across like a scene from the Bourne Identity movie, and that’s precisely the point. It will bring some adventure, absurdity, and shock value to the conversation.

Deep first date questions for the Deepening Phase

Now you’ve touched on all the superficial questions. You’ve come to the point that a real connection needs to be made to make the date a success. It is time for something more sensual and personal. Many men stick to the superficial and dig their own grave.

Science says that asking more personal questions on a date results in a closer relationship between two people.

You are tasked with taking a deep breath and getting to know her on a deeper level. No stress, I have 12 top questions for you that save you from the deep end.

36. What are you most attracted to in a person?

By asking this question openly, you give her the chance to choose appearance or personality. If she answers the question about you, you know right away where you stand ;).

37. Which person in your life do you admire the most?

This question will connect her to her inner norms and feelings, which can be reassuring and powerful. This way, you get to know each other’s values.

38. Do you have a close family connection?

Our early childhood and relationship with our parents have shaped us and have made us who we are. For some reason, I am personally very attracted to women who come from a warm nest. But that’s just me.

39. Which advice do you wish you’d gotten from your parents when you were young?

Another version of this is: which advice would you give your younger self. This way, you find out whether she is wise and what the important lessons were in her life.

40. What is the last movie you cried to?

Again, when you ask this question, you have to be prepared to answer it. So, prepare for this by asking yourself the question too.

41. What are you the most grateful for?

Being grateful is a strong indicator of the ability to put things in perspective and for emotional maturity. If you want to know whether she is serious relationship material, this is a question you can’t skip.

42. Which pictures or paintings have had the most impact on you?

This question will paint you as having an interest in art. If that’s your thing, then this question is an excellent way to find out if it’s her thing too. Also, it doesn’t hurt if you are somewhat of an intellectual artist in her eyes.

43. Are you a good friend? Why (not)?

This question makes her have to prove herself. What does she find valuable in a friendship?

44. How do you measure success?

Success can mean different things to different people. By addressing this, you show her that you are aware of that. For one person, it could be relationships or family, and for the other, it might be their community or work. And for others, it could be all about themselves. Valuable information for your next conversations with her.

45. Which event changed your life the most?

A question that can be a real bonding tool. These cases are often hidden deep within because it’s something very fragile. If you succeed in making her open up like this, that is a huge success. This is also how she will experience it: this man is not like others.

46. What is your weirdest dream ever?

Personally, I can barely remember any of my dreams. Except for one time when I was young, I dreamt of Casper the Spooktacular. This dream gave me such a sense of unlimited possibilities, that still gives me a warm feeling whenever I think about it.

47. According to you, what is perfect happiness?

Many people have a hard time answering this question, but even just thinking about it can be useful. Besides, you will be the one guiding her when you ask this question. This makes you the leader in exploring this, which is exactly what you want.

That was it. With more than 47 questions, it’s practically impossible ever to have a boring date. Unless, of course, you’ve listed all the questions one by one.

Keep in mind you shouldn’t spend the entire date asking each of these questions in a row.

You also want to come up with interesting topics to make the date memorable.

Here’s an entire article about this, check it out:

>> 15 Best Topics to Talk About with a Girl (Texting/Dates/Tinder)

The Completion Phase of the first date

You might think now:

Don’t you have any questions for this phase?”

The Completion Phase is meant to extend the date, to set a second date, or to end it. In this phase, you won’t be asking any more questions.

For you, it should be clear at this point whether you wish to see her again or not. Or, if you would like more from here right at the moment. This is your decision now by being steadfast in your ideas.

It will not be “Shall we meet again,” but “Let’s meet again.”

Besides, we only talked about what open-ended questions to ask a girl on a first date. But I know for a fact that if you go on a date with a nice girl, you would like to walk away with a kiss.

For that and more I created the free Transformation Kit for you.

This will provide the tools and mindsets to fall back on when you’re drawing a blank on a date. It will also help you being an all-around boss who never aches for a date again.

Get it here, it’s free!

Your bro,
Dan de Ram

Stop awkward conversations
and painful rejections

My free Transformation Kit will make you irresistible to women.

  • 12 Opening Lines that Actually Work
  • 5 Date Generating Texting Tips (Plus Copy-Paste Lines for Tinder)
  • The Friendzone Escape-Room Trick
Yes, give me the Transformation Kit!

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  • Gali says:

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    helpful info with us. Please keep us informed like this.
    Thanks for sharing.

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