50 Questions to Ease Your Girl Into A Conversation

Questions to ask a girl

For some of you guys, conversation with a girl you like kicks off smoothly and flows effortlessly. Time seems to fly by. Before you know it, it’s been a couple of hours and you have had a wonderfully engaging conversation. That is great, but you certainly are a minority. For most guys, attempts to get the conversation going can be hard labor. After what feels like 2 hours, you realize it’s only been half an hour of disjointed conversations with numerous breaks of awkward silence, in which you are both wondering what to say next.

Here is a compilation of 50 questions you could ask to get things revved up. These will set you up for fun, interesting discussions and maybe even a good laugh.

These questions are categorized based on the kind of information her answers will reveal. These are:

  • Her interests, likes, and dislikes
  • Her values and beliefs
  • Her family and past
  • Her hopes and aspirations

If you are thinking about getting her a gift, questions on her likes and dislikes will give you a few ideas. On the other hand, if you are looking to get a deep understanding of who she is, questions about her beliefs and values will give you some useful information. In the final category, we have included some totally random and maybe silly questions. The purpose of these is simply to get your creative juices flowing and let your imagination run free.

Questions to ask a girl

  • Her interests, likes and dislikes

From these questions, you can learn something about her favorite things, personal opinions, and even what upsets her.

Question 1: Which era in history had the best fashion?

She will like this question whether she is a fashion enthusiast or not. She will definitely have an opinion on this and you are almost certain no one has ever asked her this one before.

A good follow up question is whether some eras were better for men’s fashion and others for women’s fashion.

Question 2: What’s the one silly thing that gives you the creeps?

We all get creeped out by something. It will be amusing to hear a funny story about her fear. Though the question doesn’t refer to deep, intense fears, it can elicit a strong response.

You may choose to talk about deeper fears or keep the conversation light with more stories of comical fears from both of you.

Question 3: What do you like most about being female and what do you hate about it?

She will definitely have a lot to say about this. Be warned, if a conversation about female biological processes makes you uncomfortable, you should probably skip this question altogether. Besides, you may just learn something new. Women have to deal with all sorts of mysterious pains and discomforts all the time, so men should at least try to understand them; even if they are so very glad to not have to go through these things.

If you do end up enjoying this one, there are lots of interesting follow-up questions. If her answer has anything to do with bodily processes, don’t probe too much. However, it will probably be fun to hear what she likes about being female. You could also share what you like and dislike about being a guy.

Question 4: Name one thing you find terribly annoying.

It will be interesting to learn what gets her ticked off. She may describe something that you both find annoying. It’s always nice to discover something you have in common. If you intend to have a long-term relationship with her, then her answer here should probably be something you want to keep in mind.

Question 5: What is your favorite show on TV?

Yes, this is a fairly common question. However, it’s great for conversation because if you happen to like the same show, you will have a lot to talk about. If you are not familiar with the show, she will definitely enjoy telling you what it’s about and why she likes it.

Question 6: What world famous monument do you think is over-rated?

From her answer to this question, you will learn what she is not interested in. You will definitely hear some interesting answers, and learn if she likes to travel.

Question 7: What is the one thing you are convinced people are just pretending to like, or have been misled into liking?

This is definitely not a common question but can elicit some fascinating responses. It will give you a good indication of what crazes and tendencies she finds meaningless.

Question 8: Who is your favorite actor or actress?

This is another common question, but one that is sure to tell you what kind of movies she likes. It would be a great way to get the conversation going if you happen to like the same actor or actress.

It is also a great gateway into a general discussion about movies, assuming that she likes movies – as most people do.

  • Her Values and Beliefs

These questions will give you a glimpse into what is important to her. They reveal her principles, standards, and qualities she believes to be acceptable in herself and others.

Question 1: Has a stranger made a big impact on your life and why?

This is an uncommon question. She will probably take a moment to think about her answer. Nevertheless, it can only make the conversation more interesting because her answer will likely be a thought-provoking one. Besides, it presents an opportunity for her to tell you a story from her past and its impact on who she is today. It never hurts to have this information.

Continue the conversation by asking for details about her story or other strangers who have impacted her somehow. You may also share your story on the same subject.

Question 2: Which achievement do you take pride in but most people would think is silly?

Her answer to this question is a great way to learn more about what she values. If she is your girlfriend, you could use this information to come up with a fun, competitive game to play together.

Question 3: How early do you make conclusions about people?

Use this question to find out what she thinks of other people and what stereotypes she may hold. Ask her what opinion she had of you when you first met. You could also ask what she looks out for in determining if a person is a good or bad person.

Question 4: How different would the world be if superheroes and supervillains were real?

If she likes comics and superhero movies this one will be lots of fun. This genre has become quite popular. No doubt it will get you both thinking. Let your imagination run wild with make-believe stories. You will probably get to learn which evils in the world she feels should be addressed. If she doesn’t enjoy superhero movies at all, skip this question.

Question 5: What would be the most beneficial change to your country’s education system?

Her answer will probably reveal her take on social change and perhaps give you some idea on her political inclinations. You may find that she feels very strongly about this issue and may give you a long passionate speech about what needs to be done. On the other hand, you may find that she really doesn’t care much about it. Whatever the case is, it will give you valuable information. If it is something she is interested in, you can then discuss the strengths and weaknesses of your individual ideas.

Question 6: What aspects of your culture do you take the most and least pride in?

Our culture forms a significant part of our overall identity. Whether this question leads you into a deep philosophical conversation or not, it will give you a great conversation. I will be fun to discover where you share opinions and where you have different views.

Question 7: Who was the worst guest you ever hosted in your home and why?

This one will definitely see you both have a good laugh. You will enjoy it because it presents an opportunity for her to tell a story. Be sure to ask for details and ask lots of questions after she tells her story.

Question 8: Do you believe that humans are fundamentally different from animals and why?

Be warned, this is a serious one. Brace yourself for a discussion around religion, faith, perhaps science and other strong convictions. This one is best tackled with a fair sense of seriousness. Light conversation is fun, but a good deep conversation can be very refreshing. If you like to keep it light all the way, leave this question out.

Question 9: What pictures or paintings have made an impression on you?

She probably hasn’t heard this one before. In fact, she’s probably never thought about it. You will have fun with this one because she is likely to have lots of answers. You can do a quick Google search of these pictures and paintings on your phone and proceed to discuss as you look through the images.

Question 10: Which societal ill is becoming increasingly acceptable but shouldn’t?

The main intention of this question is to begin an engaging discussion about society. You will probably find out which movements she supports or is against. Keep in mind that it’s perfectly in order for you to have varying opinions. This will even make the conversation more interesting. Remember, you are not out to spark off a serious debate and you need not convince her that you are right about anything.

Question 11: What are some signature characteristics of a creepy guy?

Every girl has come across a guy she finds creepy. Ask her what exactly it is about them that makes them seem as such. Are they actually creepy or just different in their own kind of way? You will certainly learn something about how she views herself and others.

  • Her Family and Past

From these questions, you will learn a lot about her family, childhood and general experiences from her past.

Question 1: What weird tradition does your family have?

Every family has its unique, sometimes silly practices. In many instances, children don’t realize these are abnormal until they are much older. From her answer, you will get to learn something about her family and perhaps how she grew up. You should share something weird about your family as well.

Question 2: What’s the most immature habit your parents have?

This is another question she will most likely be hearing for the first time. No matter how old we get, we all have some annoying habit we never grow out of and parents are no exception. Some are silly and fun while others are annoying. Whichever kind she chooses to share, you are assured of an interesting conversation.

Question 3: What is your earliest childhood memory?

Research shows that most people’s earliest memories date back to when they were between 3 and 4 years old. This question will shed some light on her childhood, but not much about who she is today. Either way, it will be fun to hear the story of her first memory.

Question 4: What are you totally finished and done with?

The best part about this question is that there is no way to predict which way it will go. Her answer could be about a past fashion fad, past hobby or a relationship. It could be absolutely anything. Whichever way it goes, the truth is that everyone loves talking about things that upset them. She will too.

Question 5: What memory keeps popping back into your mind?

This one will give you a bit more information about her and her past. She may share a serious memory or one of those random memories we all have. Whichever she chooses, this certainly gives you a clearer picture of who she is and her past.

Remember that if she chooses to describe a serious memory, the conversation may get heavy or emotional quite quickly so be prepared for that.

Question 6: Who have you been out of touch with and hope they are well?

She has no choice but to reveal something about her past. It is a perfect way to get to know her a little better. She will enjoy reminiscing about the person she mentions. Even if you don’t know the person she talks about, they are or were important to her. That’s why it’s worth it to listen.

Question 7: What have you always struggled to do well but with no success?

Sharing flaws and shortcomings make people closer. It is difficult for anyone to openly share their weaknesses so if she shares a deep, heartfelt one, try to be as supportive as you can. The last thing you should do is laugh or make fun of her about it. You can follow up this question with one to establish if she is still trying to learn the skill or happy to never have learned it.

Question 8: What is the most inconsequential reason someone you know has lost their temper over?

This one will definitely dig up a good story. You can also tell her your story on a similar experience and have a laugh. You can be sure of a great conversation.

Question 9: What question do you wish people would quit asking you?

No matter what stage of life you are in, there will always be a couple of questions you have heard too many times. It could be concerning anything from your marital status, career or future plans. This could provide a good opportunity for her to vent. When she answers the question, keep it in mind so you never make the mistake of asking it to her.

Question 10: What’s the most absurd disagreement you have ever had?

With this one you are assured of a humorous story, which she will enjoy narrating. Feel free to share some of your own ridiculous squabbles. You will probably have lots of these to share, especially if you both have siblings.

Question 11: What’s the greatest life lesson you have learned so far?

This is a serious one which would form a great opener to the conversation. It will reveal some of her beliefs, values, and explain why she is the person she is today.

Question 12: Who was the most power-mad person you have ever met?

Yes, this is an odd one but even the oddest ones have a potential for a really good conversation. If you find it a bit too unusual for your liking, feel free to leave it out.

Question 13: What’s your most embarrassing moment around someone you had a crush on?

This question may not be ideal if you have just met. However, if you have known each other for a while and are comfortable with each other, this is a great one. Prepare to cringe when she tells her story.

  • Her Hopes and Aspirations

Find out what she would like to achieve in the near and distant future. Also, get to know who she admires or would like to emulate.

Question 1: Is there something you will one day regret not starting now and what is something you wish you had started earlier?

We have all procrastinated before. Through her answer to this question, you will learn if she procrastinates a lot, what she values, and some of her future goals. It’s a good idea not to focus too much on what she hasn’t achieved because you don’t want to make her feel worse than she already does. You could also share with her something you have procrastinated. Finding shared goals and aspirations will definitely get the conversation going.

Question 2: Which movie or book character are you comparable to?

This one is interesting because it will tell you something about her self-image as well as the kind of person she aspires to be and it never hurts to have this kind of information. Consider breaking this question into two parts. The first being one asking her which character she would like to emulate and the second, which character is actually like her. Alternatively, take a slightly different angle and find out which books and movies she likes. Better still, you could discuss which characters she finds most intriguing.

Question 3: What are you most passionate about and what would you like to be that zealous about?

Her biggest passion sheds light on the very core of the individual and tells you how she views herself. Her answers will reveal something about her likes and dislikes as well as the kind of person she would like to be. She may also share her immediate future plans or long-term aspirations too.

Question 4: What’s the one place in the world you would not like to go?

Here, you turn around the stereotypical question of one’s dream destination. It is fun because she may decide to answer it literally or make fun out of it. You cannot predict her answer. She will probably need to think about it and whichever way she takes it, it will lead to a great conversation.

Question 5: Who is the most humble person you have ever met?

Yes, this is somewhat random. Nonetheless, it will give you some knowledge of the kind of company she keeps and the kind of people she admires.

Question 6: What application on your phone is underutilized but shouldn’t be?

This is a nice twist to the popular question on one’s favorite or most used mobile phone app. We have all, at one point or another, had a self-improvement or educational application which we intend to start using but never did. This may lead to a discussion about mobile phone apps and can get very interesting.

  • Funny, random questions

Now go ahead and enjoy exploring all sorts of hypothetical ideas. Your imagination is your only limitation.

Question 1: How would you plan to survive an apocalyptic epidemic?

With all the post-apocalyptic shows, movies, and books out there, you must have thought about it. You can enjoy a lengthy discussion on the advantages and disadvantages of each plan and compare different scenarios. If you are both fans of the post-apocalyptic genre of books and movies, you will love this one.

Question 2: If you could transfer your brain into a robot and live indefinitely would you do it?

This is a fun, speculative question which could get a bit philosophical. It raises questions of the humanness of such a robot. You could discuss the pros and cons of indefinite living. Alternatively, keep it light and talk about how much fun it would be to have a robot body.

Question 3: If we couldn’t shake hands as a greeting, what other interesting greetings would you propose?

This one will definitely give you both a good laugh. Try a few greetings such as high-fives with elbows. Get creative and have fun while you’re at it.

Question 4: When does time seem to fly for you and when does it seem to drag?

You will find out which activities she enjoys and what she finds boring. Ask her for more examples of activities that interest her. Alternatively, prompt her by randomly naming activities and see which ones she gets excited about.

Question 5: What usually sounds like a good idea at first but turns out not to be?

You should have fun with this one. Everyone has some hilarious stories about good ideas gone bad. Share a couple of stories and see who has the funniest and craziest one.

Question 6: Which fact are you surprised is not more widely known?

Think of facts that the other person probably doesn’t know and share them. We all love learning new things. You will not run out of interesting pieces of information to talk about. Take time to talk about each of them rather than shoot one fact after another.

Question 7: What’s the best comeback you’ve ever heard?

You will definitely have fun and some laughs with this one. She will probably have some comebacks you have never heard before and great stories to go with them. You can share some of your interesting comeback stories as well.

Question 8: What is the weirdest phobia you have?

The answer to this one could be funny or very strange. Whichever the case, you will enjoy the conversation. You may just find that you have a common phobia.

Question 9: Who (living or dead) do you think would be the ideal leader for our country?

Here is a political question which requires a bit of creative thinking. From her answer, you will learn what kinds of developments she would like to see in the country or perhaps she really doesn’t care much about politics.

Question 10: What was a joke that went way too far in your experience?

Stories about jokes are always fun to hear. However, we have all heard of practical jokes gone too far, leading to an unpleasant experience. Therefore, be warned that the story could end up being a dark one. Either way, give it a try and hope you can have fun with it.

Question 11: What is one thing that you want and/or need but doesn’t exist?

She will require some creative thinking to answer this one. It will be interesting to hear what needs she talks about and what solutions she has in mind.


There is no shame in putting some thought into what to talk about before you go out to meet her. So go ahead, try some of these and see how quickly you ease into a natural conversation. When you find a topic you are both interested in, feel free to spend some time on it. Don’t be too eager to move to the next question. After all, it’s a conversation, not an interrogation!

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