You have had your eye on a girl for a while and you finally asked her the very important question about whether she would like to go on a date with you. 

Now, you’ve asked her the most difficult question, but perhaps you’re now wondering what do you talk about once you hit the night on the town?

Questions to ask your date

What questions should you ask?

What if they’re the wrong questions and make things awkward? 

Well, we’ve put together a long list of different interesting questions to ask a girl to give you a helping hand, no matter the type of date or the topic of conversation. 

Keeping It Fun

Firstly, you need your date to be fun if you want the girl to want to see you again.  

Keep the conversation light on your first date.

Your questions should reflect levity and fun rather than getting too heavy or serious. Equally, you don’t want your questioning to appear like she’s being grilled for information.

This is especially important to bear in mind if you met the girl online and you are just getting to know her.  It is very easy to want to rapid fire questions, but that is simply obnoxious.

She doesn’t want to feel like she is being interviewed for a job. 

Also, remember, you are not trying to see if she is the right girl for you immediately.  You first will want to put her at ease and create a fun and relaxing conversation so that you can find out more about her, and her you!

Simply put, your questions need to be fun rather than serious, at least at first.  So, what could you ask her?

1. If you could have any super-power what would it be?

This question could let you in on what kind of person she is. Is she adventurous and wants to fly? Or is she a gossiper and would love to be invisible, finding out things that she’s not meant to? 

2. What was your favorite childhood toy?

Does this match up with what you would have thought? Does her answer surprise you? Is it similar to what your favorite toy was?

Listen to her answer as it will tell you some things about her.  Was she drawn to her baby doll? Or her Lego sets?

Talking on a first date

This could give you a clue as to whether she’s nurturing or creative, for example, or perhaps even traditional over rule-breaking. 

3. Where would you go if money were no object?

With this question you can learn all about her traveling desires and how they compare with yours. 

Does she fancy exploring the bush in Australia or would she prefer lounging on a beach in the Maldives? How does your ideal destination compare to hers? 

4. If your elevator broke down and was playing a song on repeat, which song would you choose?

This will tell you her taste in music by allowing her to pick only one song. It might open up the reasons as to why it’s her favorite song. Or, it might even show her intelligence.

Someone may decide to pick a song they already hate so that they don’t then associate a song that they love with being stuck in an elevator for hours. It will give you insight into her way of thinking!

5. Tell me about the best present that you’ve ever given anyone.

This one opens up insight into her thoughtful side. 

It will tell you if she’s someone who puts a lot of thought into gifts for her loved ones or whether gift giving is something that she does not put much effort into. 

Giving good gifts

In addition, it will help you gauge if her love language is gifts. It may let you know if you’re compatible in this way.  Will she always expect lavish, expensive gifts from you? Or does she value experience and thoughtfulness over cost? More importantly, are you on the same page in this respect? 

Would You Rather?

If you’re at the playful and flirtatious stage in your relationship, a game of “Would You Rather” is certainly one way to have some fun when thinking of interesting questions to ask a girl.  

If you have never played this question game before, it essentially works by asking each other questions that only have two possibilities, with both options being either really obscure, equally appealing or not appealing at all.

Being playful on a date

By asking your girl these types of questions, you are bound to make her laugh and have a little bit of fun.

But, not only that, the responses she gives will be interesting and will lead into great topics of discussion which will let you into her world and allow you to get to know her that little bit more. 

Let’s have a look at some ‘would you rather’ style questions:

1. Would you rather always be half an hour early or always be ten minutes late for the rest of your life? 

This question will tell you how she values her (and your) time.  Is she one of these people that is annoyingly perpetually late and thinks she can’t help it? Or, does she respect the others persons time enough to want to arrive early and be the one waiting?

2. Would you rather be unknown whilst you’re alive and then famous after you’ve died, or famous whilst you’re alive but forgotten when you’ve died? 

This question will let you know her values.  If she likes being the center of attention, she’ll surely choose the latter.  But, if she values her privacy but wants to leave some sort of legacy, she will choose the first option. 

3. Would you rather have a dream job but work until you die or have a horrible job and then be able to retire in five years’ time? 

This question will let you know how resilient she is to short-term pain for long-term gain as well as how important she sees her career and work as a part of who she is.  

4. Would you rather go 500 years into the future or go back 500 years into the past? 

This question lets you into whether she values past experiences and learning from history or whether she is more forward thinking and curious about the path that humanity is taking. 

5. Would you rather be able to transport yourself anywhere instantly or be able to read people’s minds? 

The first gives you absolute freedom, the second will give you unrivaled insight into others. 

What will she choose? 

Past Experiences

This is a topic for questions that could take you into difficult history if it crosses over into past relationships!

However, this depends on how long you have been seeing a girl.  If it’s a first date, bringing up exes is an absolute no-no.  But, if it has been a while, it might be a territory that you want to wander into.  

Man and Woman Sitting on a Bench

Asking questions about the past, even if very recently, opens up a dialogue about how the girl you’re seeing approaches life and whether or not she lives with any regrets, and more importantly how she manages those!

This will tell you a great deal about what kind of person she is deep down and any rules that she lives by.

It will also tell you how well she has maintained relationships in the past and what her downfalls are (if, indeed, there are any!). 

Let’s have a look at how you could gently probe into her past. 

1. Are you still in touch with your childhood friends? 

This question will let you know how much she values friendship as well as letting you know what she values in a friend, which ultimately is what she will end up valuing in a potential life partner too. 

2. What’s the most impulsive thing you have ever done? 

How daring and brave is she? Or, how stupid? Remember, impulsivity might be something silly that isn’t daring or brave but outright dangerous.  Where does she lie in this question? 

3. Is there anything you are ashamed of having done? 

Phew, this one will surely bring out skeletons from the closet if there are any! But, depending on where you are in your relationship (or just how bad her past experiences are), it might mean that she’s not ready to share yet.  Only ask this question if you feel she’ll be honest and not put off! 

4. What were your thoughts about me when we first met? 

We all know that first impressions count.  Apparently, according to the best-selling book, Blink, we make our first judgments of someone within the first six seconds of having met them. 

What were her thoughts about you? And, are you ready to hear them? 

5. What is your first memory? 

This will allow your girl to open up about her childhood, usually. 

You’ll be able to learn more about her family and her upbringing and, most importantly, if it was a happy one. 

People who have had difficult childhood experiences often find it difficult to have successful adult relationships through no fault of their own. 

Woman Smiling in front of blackboard

Finding out about her past and her upbringing might mean that you’re more prepared if any demons surface or might mean that you’re able to support her more effectively if something difficult should arrive in the present. 

6. Have you ever had your heart broken? 

This is getting deep! Remember, you should only stray into asking this type of question if you’re prepared to hear the answers!

If you really don’t want to listen about your girlfriend’s exes and how they broke her heart, then steer clear of this one. 

If you’re a jealous type or know her exes, then this one is probably best to avoid!

Future Expectations

We have looked at questions probing into her past, now it’s time to get serious and think about your future together. 

These questions are important ones. They will help you assess whether or not you and your girlfriend want the same things out of life and whether you have any shared goals. 

So, what could you ask her? 

1. If you had only one day left to live, what would you do? 

This question allows her to pinpoint her priorities.  Usually, people answer this question by saying how they would want to spend it with people – maybe in a certain special place.

Whatever they choose to do, it’s usually with the people they value the most. Are you a part of her plans? 

2. If you won the lottery tomorrow, what would you do? 

Asking this question not only lets her tell you her priorities if money were no object, but it tells you her dreams for her life. 

  • Travel?
  • Buy a big house in the country?
  • Give some away?
  • Set up a charitable organization? 

These answers tell you what is important to her.

3. What’s your greatest fear for the future? 

This is a deep question.  For most people, it is usually something to do with dying or others dying, but it might be something to do with security in life and whether she will have enough money to keep a roof over her head. 

Does she fear the future at all? Not all of us do! For some of us, we see growing old as a privilege, rather than a right.

Where does she sit with this question? 

4. Do you believe anything happens after we die? 

Is she spiritual, scientific, religious? For most of us, we seek out a partner who has similar core beliefs to ourselves. 

If your core beliefs don’t align in any way, are you both at least respectful of the other person’s beliefs? 

5. Where do you see yourself in five years’ time?

 This is a thought-provoking question! Depending on how long you’ve been dating someone (if, indeed, you are dating!), whether or not you are a part of this equation is quite telling.

Does she talk about her career and leading her own path work-wise?

Does she mention marriage and children, and if she does, are you led to believe it’s you who she is thinking of?

Woman enjoying sunny day

If not, there is no reason to panic just yet. Remember, she could be being reserved and cautious in case you’re not on the same page as her. 

Perhaps offer your own answer to this question, to see what her response is. 

What NOT to Ask

We’ve talked a lot about things you can ask the girl you’re interested in, but is there anything you should avoid asking?  Well, the obvious answer to this is yes, absolutely. 

However, it does depend on your existing relationship and where you’re at with it. 

If you’ve been seeing each other for a few months, then some of these questions are absolutely ok to ask!

But, if it’s a first date or you’re trying to get that girl in the office to go on a date with you in the first place, some of these questions are certainly best avoided. 

1. How old are you? 

Don’t just come right out and say it! Women can be touchy about their ages, both if they’re deemed ‘too young’ or if they’re thought of as ‘too old’.  Steer clear until you know her better. 

2. Is that what you’re wearing tonight? 

Do NOT make any such comment on her clothing choices for a date.  She will most certainly run for the hills and not call you again. Likewise, have you put on weight? 

3. How many guys have you been with? 

It might be obvious but do not ask a woman how many previous partners she’s had.  I know you’re interested, but it is just rather too personal and nosy.

If the number is a lot more than you think, are you going to judge her?

Close up of girl's eyes looking at camera

Are you going to think “Wow,  she’s easy, hopefully, she’ll let me be number X…”, or will you think “Woah, that’s way more than I thought, I’m not sure I can go out with someone so promiscuous!” 

If the number is small, are you going to think she’s really inexperienced and therefore not for you? Or is that what you want to hear?

Either way, girls cannot win in this situation!

Too many, too little, whatever girls answer, it won’t be what you want to hear.

And, I’m sure it’s no surprise, but girls usually lie about this number anyway for fear of judgment. 

4. Is it that time of the month? 

She’s a little cranky. But a sure-fire way to annoy her further is by suggesting it is something to do with her menstrual cycle! 

5. Why are you single? 

This can be perceived in lots of ways: as a judgment, as a criticism, as flattery. 

But, trust us, just avoid it! 

The Take-Away

With a bit of luck, having some questions in mind to ask the girl you’re seeing or want to be dating will help you fill any awkward silences as well as letting you get to know her on a deeper level. 

Interesting questions can be a fun ice-breaker but also can reveal deep secrets and thoughts that she’s ready to share.

However, it’s important to remember that your dates are not meant to be interviews! Don’t have your list of questions there ready to fire at her.

Allow your conversation to flow naturally and maybe set aside a few questions you want to ask on each date rather than all at once.  

Couple Laughing near Handrail

Life is full of questions.

Our curiosity doesn’t diminish because we’ve left our childhoods behind.  Questions play an important role in our lives. From “what’s your name”, “will you go on a date with me?” right through to “will you marry me?”. 

Life has its ages and stages and questions to suit each and every point.

Hopefully, we have helped you today with some interesting questions to ask a girl, no matter what stage of life you’re at.