Conversation Starters: 20 Questions To Ask The Girl You Like

Love is in the air when you are dating the perfect person. However, when it comes to knowing her a little better, you are stumped. There are many questions you want to ask her, but you aren’t sure how to go about it. Well, we are here to help you broach the subject. 

Asking a string of questions can feel like an interrogation, and when you have found the perfect person, you don’t want to do anything to mess up anything. 

For some, conversation comes naturally, while others struggle with it. With our list of “questions to ask the girl you like,” you will never falter at conversation. When you come prepared with these fun and interesting questions, things will run smoothly. 

Ground Rules

However, girls aren’t always easy; you need to tread carefully when asking questions. Consider the following before trying to know her better. 

  • Courting isn’t easy when you lack at making conversation flow; so take it slow. Keep your pace steady when asking questions; you want to make them feel like you are interested in knowing them rather than interrogating them. 
  • Don’t ask random questions; that’s creepy! Make sure your questions always have context.
  • Don’t just leave her with her answer; follow with your own experience and answer the same question too. This will keep the flow of the conversation. 

In other words, it should not be a one-sided affair. 

Now that you know the etiquette of asking questions, here are some of the best inspirations that will help you strike up the perfect conversation with your love interest. 

1. Dog person or a cat person?

Talking about people’s pets or if they wish they had a pet is a great conversation starter. If this is the first time you are meeting this girl, this is a safe question to ask. However, keep it at that, don’t start about your long list of pets and how much you love your dog, and don’t even think about showing them your pet’s most adorable pictures!

If you both are dog or cat persons, you can have a great conversation comparing the lifestyles of your pets. However, if you both have different choices, you can agree to disagree and move on to the next one. 

2. One day left to live…

If the conversation is stalling and you both are running out of things to talk about, you can start asking speculative questions like, If you had one day left to live, what would you do first? 

Now, this is a cool question, you can give your answer first to inspire the girl to provide a quirky and interesting answer, or you can let her answer first and then agree or disagree with her choice. Either way, this question will pick up the conversation in no time. Such questions always get interesting ideas and replies; these are enough to get the conversation going without boring the girl you like. 

3. What do you like most about yourself?

Ask them what they don’t like about themselves, and there will be a long list, but when you ask them what they adore about themselves, there is always a long pause to think unless you fall for a vain girl. 

If she is full of herself, she can go on and on about the stuff she likes about herself; if not, she will stop at one or two traits. You can then pick up the conversation and praise her some more. This question allows you to flirt and praise without being too obvious. 

4. Astrological Sign?

A majority of the female population believes in astrological signs, daily horoscopes as well as the most compatible sign. If you are a believer as well, this can be the perfect question to take the conversation forward.

Ask her what her favorite sign is, and then keep the conversation going about what you know about her sign. If she believes in star signs, she will have her information to add to yours. But if she isn’t into astrological signs, she might get interested in your information about her astrological sign.  

You can easily spike up her interest by telling her good parts of her astrological sign like positive traits, strong suits, etc. Again, this is a safe question and doesn’t need context. 

5. Favorite TV Show?

Discussing favorite tv shows is yet again a good one; this can keep the conversation going for a long. However, there is a catch, she may not watch the same shows as you? or she doesn’t watch TV at all. The conversation just might end at I don’t watch TV much. You can then take the conversation toward Netflix or Amazon Prime; these two are trending atm so you might be in luck. 

6. A Fictional Character You Identify With the Most

Believe it or not, girls are more interested in fictional characters than real people, so this will get the conversation going. Books, shows, and movies have characters inspired by real people, but more honest. These characters are shown with their true personalities, making people relate to them more than the next human being. 

This is a good question if you are looking to get to know the girl as well as keep a healthy conversation going. Knowing the fictional character she most relates to will help her understand the fold of her personality. This will help you get closer to her. 

7. What does your Dream House look like?

Everyone has a different dream when it comes to houses. Some like cosy, while others want a more modern and chic look. Whichever style it is, this question will surely last a long while. 

You can compare notes about your dream house too. You never know; may you both have the same choice and will be able to bond over this question. You can even branch out this question and talk about decorating styles, color palettes, and the kind of appliance you must have in the house. 

8. Do you prefer crosswords or word searches?

For geeky and nerdy folks, this is a super question. However, this one might be a good icebreaker, but it might fizz out quickly if she isn’t, either. 

9. Love at First Sight, Opinion?

Now, this is a total flirt question to ask any girl you meet at the bar. There are many cheesy pickup lines around this subject of love at first sight as well. However, it sounds totally different when you ask this after you have established a connection. So, pick your time carefully. How do you want your question to sound, cheesy or meaningful?

10. Ultimate Travel Destination?

I know a great many people who fall in love with places more than people. If you ever meet a travel fanatic like that, be sure to ask them about their ultimate travel destination. Also, prepare for the longest answer and conversation because it can be a long while until they stop talking. 

Make sure to make the right sounds and look interested when they rattle on and on about their favorite place. 

11. Dream Super Power??

This might be a cliche, but it’s also a great conversation starter. If you want you can also add a cheesy pickup line to this, but if you really like the girl and want a decent chance to win her over, we say keep the pickup line to yourself. 

You can also get her an elaborate answer about the kind of superpower you would like as well. Moreover, you can mention the female superheroes that you admire just to score some extra points. 

12. Favorite and Most Treasured Memory?

Most people have a great childhood, however many had a traumatic one, so stirring clear of the childhood subject, you can ask them about their favorite memory. If they talk about how the memory is about their childhood, you can easily switch to the happy childhood conversation. 

This question may not look like it, but it’s pretty personal and deep, and it can also reveal a lot about the girl you like. But there is also a catch since this is a pretty personal question. Some might not open up and let the question pass. So, make sure you have a backup question if this one fails. 

13. Do You Wish To Be Famous, What For?

Here’s your backup question if the memory one fails. Ask the girl about what she wants to be famous for if she is looking for fame. Prepare yourself for the answer because this can go either way. 

You may get a shallow answer or a very deep one. Either way, you will learn how your girl thinks and operates. This one will give you a little bit of insight into her personality. 

14. Name The One who Knows You In and Out.

Now this one gives you an insight into who she is the closest to. It can be anyone, and it will also tell you who the most important person in her life is so that you can get close to them as well. 

15. What’s Your Biggest Fear

Again, one of the many personal questions you can ask her. The most common fear is of creepy crawlers, then comes common fears like height, water and closed spaces. Come prepared; if you know a fun fact about her fear, you must share it to distract her from it or help her get over it. 

16. What is Your Ideal Dream Date?

Asking a girl about her ideal dream date is the best way to get an insight into what she expects a guy to do for her. Make sure you remember even the smallest detail of this one so that it’s easier for you to propose to her when the time comes. 

This question will also help you ask her out and give her the best date of her life, just like she would love. 

17. What celebrity would you switch lives with?

Celebrity lives are larger than life, and most girls follow their favorite celebrities big time. So, this question will also get a stale conversation back on track. 

18. Three Things that you are Most Grateful for Today? 

As the subject of happiness and how content one is in his life comes around, you can ask your girl to tell you about the three things she is most grateful for today. 

I am sure there must be many, but you need to look out for the most important three to understand how she operates. Family, money, stability, a good job, a home, or friends all of these are positive pointers that you need to look out for. 

19. Twenty-four hours Aren’t Enough For What? 

We all know how 24 hours in the day aren’t enough to do everything that we need to do. Many things get left behind because there aren’t enough hours in the day. So, ask away what she would want more of that she isn’t getting the time for. You must also have something to share in this regard, don’t hold back. 

20. Do you think money can buy happiness?

Last but not least is the debate about whether money can buy happiness or not. Lately, you get to hear more of the yes side; money can buy happiness, but what does your girl think and why. 


There are many questions you can ask a girl to know who she is. These questions are designed in a way to get their true personality out. These will also help you gauge how deep or shallow they are. However, make sure there is a connection before starting on your random questions with the girl you like.