55 Good Questions to Ask on a First Date

In this article, I will share 55 questions to ask on a date, which works no matter if it’s your first or one-hundred-and-first date with her. For your convenience, I decided to divide it into the following sections:

• Ten flirty questions to ask on a date
• Ten fun questions to ask on a date
• Fifteen cute questions to ask on a date
• Ten romantic questions to ask on a date
• Ten personal questions to ask on a date
• PLUS… a handy guide that will help you make your next date extra special

Now you will get everything. If there is a button or link that says “read more” below this line, you need to click or tap it since I will share every question you need to ask her on your next date.

Flirty Questions to Ask on a Date

The best way to start a date is to start slowly and warm her up. The first question you should begin to ask her is what she wants to drink, but after that, you should follow up with one of these ten questions that are flirty by design:

1. What’s the scariest thing you have ever done? By asking her this question, you will find out how adventurous she is.
2. What’s the farthest you have ever gone on a first date? When she answers this question, you will know how far she is willing to go with you on a date, but without leaving her comfort zone.
3. What makes you feel happy? This question is excellent since it opens up many follow-up questions depending on her answer.
4. What is the weirdest date you have ever been on? She has probably been on more dates than you, which can open up some exciting things about your strangest experiences.
5. Who was your first crush? Her honest answer will give you insights into what kind of guy she liked growing up. If she had a crush on someone in a band, you could start talking about that next, for instance.
6. Have you ever dreamt about dating a celebrity? If she answers yes, it can open up some other topics about that person, and you might ask her out to a concert or the cinema, depending on that person’s walk in life.
7. Have you ever sent a rude text to someone by mistake? The answer will reveal if she isn’t very tech-savvy or if she only sends that kind of text when angry at you.
8. If you could spend seven days anywhere in the world, where would it be? Her answer might surprise you.
9. How would you rate my looks on a scale of 1 to 10? If you have put some effort into your preparations before the date, you want her to notice it. That’s precisely what this question will help you answer. You will also realize if she is good at spotting details or not, which might come in handy further down the road.
10. Have you ever been in a long-distance relationship? If she has, you might talk a little bit about your experience as well, or lack thereof.

These questions are great conversation openers and will help you get to know her better. Here are 55 conversation openers she can’t resist.  

Fun Questions to Ask on a Date

Now that you have started the conversation, you need to create some emotions in her. Remember that making her laugh has many benefits. One of them is that she will enjoy spending time with you. Here are ten questions to ask on a date to make her laugh:

1. How many doughnuts can you fit in your mouth at once?
2. Do you put the toilet paper roll in the right way or the murderer’s way?
3. Have you ever wished you were a celebrity?
4. How many seconds into the first movie theatre preview do you finish your bucket of popcorn?
5. Have you ever won a hot-dog-eating contest?
6. Who would you instead be dating? A complete douche who is rich beyond your wildest imagination or someone who knows how to treat you and is always lovely and supportive?
7. Can I trust you never to pressure me into liking one of your tweets? Ever. Like, not even if we get married?
8. How many days do you wear the same pants in a row before it becomes a problem?
9. Which animal do you think has the funniest name?
10. What would you instead do on your next birthday? Scuba diving or parachuting out from a space shuttle?

You might not know it, but science proves that making a woman laugh increases her chances of getting another date. When a human laughs, the brain experiences a rush of endorphins, the “feel good” hormone, which makes you more relaxed and less stressed since it reduces the cortisol level. This stress hormone triggers the fight-or-flight situation when you are in a dangerous situation.

Most people experience a stressful situation when they meet a stranger for the first time or are performing a speech in front of an audience. The body responds like they are in a life-threatening condition. A recent study published by The Royal Society in the UK that you can read here also describes that if one person laughs, the probability of the other person laughing is 30x higher. 

Cute Questions

Now that you had made her laugh, you might want to change the mode a bit, still keeping it upbeat and easygoing but a bit more serious. In that case, you might want to ask her these fifteen cute questions:

1. What places have you visited?
2. What pets have you had?
3. What countries and exotic places have you visited or want to see?
4. What are you kind of obsessed with these days?
5. Are you a morning person or a night owl?
6. What’s your favorite international food?
7. What makes you afraid?
8. What household chore is the worst?
9. Do you want to visit other countries? If yes, which ones, and why?
10. What can I do to make your day perfect?
11. What makes you happy?
12. What’s your favorite international food?
13. What was the latest show you binge-watched?
14. How many siblings do you have?
15. If you could be anybody in the whole world, who would it be and why?

You might want to turn up the heat a bit and ask her more romantic questions, which I will discuss next.

Romantic Questions

You might want to ask her these romantic questions since I assume you have a romantic interest in her. Here are ten romantic questions to ask on a date (but you probably don’t want to ask her them on the first date):

1. What’s your favorite nickname? The answer will give you ideas on what you can call her, and she’ll probably share a story about the person who came up with it.
2. What is your love language? We all have different love languages which are deeply personal. Her answer will help you understand her preferences for receiving and giving love and offer ways to show love and affection to her.
3. What’s your astrological sign? Depending on her answer, you might want to read how you can attract each astrological sign.
4. What are your expectations for the relationship? It will help you figure out what she wants, which will help you realize if you want the same things as she does.
5. Why did your last relationship end? Her answer will reveal if she is a woman who knows her flaws, and it also tests her honesty with you.
6. Have you ever cheated on a past partner? Her answer will reveal whether she is emotionally mature since emotional immaturity is one of the reasons people break up. It will help you avoid heartbreak in the future. She might have done it to settle the score with a cheating partner in the past. You don’t want a relationship with her unless she admits it was immature.
7. What would you want to do for a living if money didn’t matter? Her answer will help you understand her goals and aspirations in life. Support and encourage her to follow them, and you will have a better relationship.
8. Do you like to cook, or do you prefer someone else to do the cooking? This question will reveal whether she loves cooking or wants you to do it. If you hate cooking, her answer might be a dealbreaker for you.
9. What’s your favorite date night activity? It does reveal if she likes a night on the town, a romantic dinner, or a cozy night at home.
10. What’s the best setting for a date night? Her answer will tell if she likes candle-lit bubble baths or binge-watching her favorite TV show with you on the couch.

It is essential to satisfy her needs and prioritize them since that will improve the quality of your relationships.

Another important priority is the date night tradition.

It would be best if you kept it going, and I am the first to admit that it can sometimes be tedious to come up with new ideas all the time.

For that reason, you might want to look at this book that shares 300 date ideas that are unique, fun, and inexpensive.

That book has helped me come up with new ideas and helped me to make quite an impression since they create unforgettable dates that are like nothing she has ever experienced before.

Now it is time to share my ten favorite personal questions to ask a woman on a date.

Personal Questions

Lastly, I want to end with ten personal questions you can ask her, preferably on a second date or even later:

1. Who is the best kisser you have ever kissed in your life?
2. What’s your favorite body part on yourself?
3. What’s your primary romantic fantasy?
4. What is the one thing that people don’t know about you?
5. What would you like to change about yourself the most?
6. What are you most satisfied with about yourself?
7. How many women have you kissed?
8. Do you have a name for your female body parts?
9. Who here are you most jealous of and why?
10. What’s the biggest turn-on to you while making out with someone?

These were the final questions that will hopefully make your next date unforgettable.

Do You Lack Ideas for Your Next Date Night?

It can be frustrating if you lack ideas for your next date night.

But no worries – we here at How to Keep Her want to help you.

If you want some date night ideas, that are:

• Exciting
• Fun
• Inexpensive (most of them costs less than $20)
• Seasonal appropriate and for special occasions in life
• Unique

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The book features more than 300 ideas that you can use to surprise her and improve your relationship simultaneously.

You know what works best with her and what date nights she likes, especially if you have asked her all the questions above, so I will let you decide if it is the right fit for you.

We have used it several times to create unique and exciting dates that have impressed women.

Asking Questions Are Great, But Action Speaks Louder Than Words

Throughout this article, we have focused on questions perfect for getting to know someone better.

Indeed, you might want to read our article “21 good questions to ask in a new relationship“, which will help you get to know her even better.

Even if talking will help you get out on more dates, she probably wants you to do more than talk with her.

For that reason, you want to make sure that you don’t just speak but also do things with her and for her since that will improve the overall quality of your relationship and convince her that you are a high-quality man who deserves her trust.

Happy dating!