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35 Interesting Things To Talk About With Your Crush And Win Them Over

Looking for some interesting things to talk about with your crush that will show them how thoughtful, funny and imaginative you are?

Then you’ve just landed in the right place!

Having a crush is one of the most exciting things in the world because all of a sudden, your life becomes more colorful, vivid and fifty shades brighter.

You feel as if you’re in a never-ending, amazing dream that you don’t want to wake up from.

Your wardrobe becomes critical and you start suffering from the syndrome of ‘not a thing to wear’ because not a single piece in your wardrobe is good enough for the purposes of impressing your crush.

Even that favorite T-shirt or sweater that you have been living in for half of your life is not good enough.

You become aware of every single detail about your appearance and you make a serious effort to look the best you can when you’re around your crush.

And even though you know that the majority of the time you’re probably overdoing it, you still can’t help it because this force to amaze is stronger than you!

And when you’re done with the exterior, thinking that your troubles have come to an end, you realize that now comes the hardest part: What to talk about with your crush?

How do you keep a conversation going and how do you talk to your crush without sounding boring or looking like someone who has amnesia and can’t remember a single event or thing that happened recently?

What are the good topics or fun topics that you should focus on and what are the topics that you should avoid (if there are any)?

So many questions running through your head and not a single topic, right?

You don’t want to risk asking something totally weird so that they get scared of you and avoid talking to you again.

And you also don’t want to sound too flirty or desperate by talking only about kinky stuff.

You want to make the best impression you can, you want to discover common interests (and maybe a few secrets)…

You want to hold a good conversation that will show them what an amazing and interesting person you are and that they should like you, too, right? Hell, yes!

And below you’ll find everything you need in order to achieve all that!


Here is a list of interesting things to talk about with your crush, separated into sections:

Topics to start a conversation with your crush, interesting topics to get to know your crush better, fun things to talk about with your crush and random things to talk about with your crush (and win their heart)!

So, buckle up and let’s get started!

Topics To Start A Conversation With Your Crush

Let’s say that your crush doesn’t know you yet or has only known you for a short period of time and you would want to initiate a conversation with them but you’re not sure how to break the ice and choose a perfect topic for that.

So, what do you do?

You focus on the current situation, you let them talk about themselves and pay attention to details that mean a lot in these situations.

Perfect conversation starters are the ones that are perfectly blended with the situation or if you’re feeling bold, you can ask something totally unexpected and you’ll get the same results because what matters is that the question is INTERESTING enough to impress your crush!

And lucky you, below you’ll find plenty of interesting topics to help you start a conversation with your crush:

1. Current situation

One of the best ways to start a conversation with your crush (and with people in general) is to use the magic of the current situation.

What does this mean?

It means asking questions that are related to the place you are in at the moment or of details that surround you.

For example, if you’re in a restaurant, you can ask your crush about certain food, telling them that you still haven’t tried that specific food and you’d like to know if it’s worth it.

If you’re at the cinema, ask them about their favorite movie or TV show.

If you see your crush on the street, you can ask them about the time or about some upcoming events in town (if there is one).

If you’re at a concert, you can ask when the band is about to perform or what kind of music they are into.

If you’re at the library, ask them to tell you more about their favorite book, the last book they read or about that one special book you find interesting.

Wherever you are, just think of the circumstances of the current situation and the right questions will come and then you can just follow up on their answers.

2. Outfit

This is also another great way of starting a conversation because we all like to be complimented on the choice of clothes we’re wearing at the time.

So, you should definitely use this to your advantage!

When you see your crush, pay attention to what they are wearing. It doesn’t matter if it’s something new or trendy because as long as it looks good on them, you can feel free to shower them with compliments.

You can say something like: “OMG, I love your T-shirt! Where did you buy it?” or, “My brother/sister has the same pants/bag/bracelet/scarf, so at the time I thought it was them.”

(Of course, this doesn’t have to be true but it has to look genuine, as if you really mean it.)

3. The latest news and upcoming events

Talking about news is a universal way of exchanging your ideas and perspectives and most importantly, it’s one of the easiest ways to keep the conversation going.

So, all you need to do is ask your crush whether they’ve heard about the latest news story and if they have (and chances are pretty high that they have), then you ask them about their opinion on it.

Also, if you’re interested in a particular event, you can ask your crush whether they’re planning to go and if they’ve been to the same or a similar event before.

Let’s say that they answer something like: “Yeah, I went a couple of months ago and it was really awesome, so I’m going again! So, you should definitely go, too.

And if you’re feeling extra courageous, you can say something like you want to go but you have no one to accompany you because your friends are out of town or similar.

I’m sure that they will tell you that you can join them and voila! You just arranged a semi-date with your crush!

4. Their habitat

In order to start a conversation with your crush and at the same time find out where they live, you can ask the following questions:

What part of the city do you live in?

Have you always lived there or when did you move there?

Do you like your neighborhood?

What would be the pros and cons (if there are any) of living in that part of town?

5. Future plans

Asking your crush about their future plans can sometimes be a risky business because they might assume that you’re inviting yourself to a certain event with them or that you’re expecting an invitation.

But screw it. Maybe the following questions are exactly what your crush needs to be asked in order to decide to make the first move:

Do you have any plans for the weekend?

Do you have any plans for your next vacation?

Are you going to (a certain event)?

6. Weather

You know what they say—if you have nothing to talk about, talk about the weather.

Actually, I just invented it but for a reason. Talking about the weather is one of the most traditional and oldest conversation starters because it’s simple and anyone can talk about it.

Let’s say you’re outside and it’s raining cats and dogs.

Your crush is at the bus stop standing next to you, probably annoyed by the rain as well, so the best thing to do at that moment is to complain out loud about the rain being a pain in the ass or to laugh at a funny situation where a car splashed you from head to toe recently.

Or if it’s too hot outside, just change perspective and complain about how hot it is and you can add some pun to spice it up with a sense of humor.

Whatever you say, you cannot go wrong with it because talking about the weather is a universal topic perfect for small talk, while it also has the power to prolong the conversation.

See also: 7 Topics And Things To Talk About With A Girl You Are Getting To Know

7. Phone charger

Since we live in a time of advanced technology, we should use it to our advantage in all aspects of our life.

So, why not in your love life as well? Asking your crush whether they have a phone charger is a perfect conversation starter because it’s out of necessity.

However, first, make sure that your phone is actually out of juice before you ask them for a charger.

Or, if you’re feeling wild, you can pretend that you haven’t noticed that your battery was 100% full, so you asked them for a phone charger but you’re now feeling a little embarrassed for doing so.

This one is guaranteed to make them laugh. And if they laugh, you’re winning their heart.

8. Pets

I’m pretty sure that 80% of love stories started with a pet.

You know the drill: You see a guy/girl walking down the street with their dog and you can’t help but ask them what breed it is and say how cute the creature is (especially if it’s still a puppy.)

So, let’s say you’re walking down the street and you see your crush with a cute dog.

So, you give the dog a few compliments and ask them about the breed and start a conversation.

Or if you also have a pet, you can talk about your own as well.

Another alternative would be social media. Tell your crush how cute their pet is on every post and that you can’t get enough of it.

I’m sure they’ll feel proud and they’ll be willing to tell you more about it and voila!

You just started a conversation with your crush! Yay!

Interesting Topics To Get To Know Your Crush Better

So, once you’ve passed the introductory part (the conversation starter zone) and you connected with your crush on a certain level, it’s time to deepen your conversations and get to know your crush better!

Here are some interesting conversation topics that you can ask your crush in order to learn more about them, their lifestyle and habits, their likes and dislikes and much more:

9. Personal history

When you really like someone, you want to know everything about their past, right?

You want to know where they grew up, the things they were into, about their friends, family and so much more.

So, here is a list of things you should consider asking if you want to know everything about their personal history:

Can you describe your hometown in three words?

Did you enjoy where you grew up?

How much did where you grew up influence you/shape you?

What were some pros and cons about where you grew up?

What games did you play with your friends as a child?

What are some cartoons or shows you watched when you were a kid?

What was your elementary / junior high / high school like?

Did you go to college? (If yes, what did you major in?)

What kind of kid were you when you were in high school?

Do you have any siblings?

Do you live close to your family?

Do you still attend family gatherings?

Do you have any family traditions?

What kind of jobs have you worked at so far?

What’s the best / worst job you’ve had?

What’s the shortest / longest you’ve worked at a job?

What accomplishment are you most proud of?

Have you won any awards or trophies?

What is the next big thing you’re determined to achieve?

10. Love and romance

Do you want to know what kind of dates your crush prefers or whether they believe in the idea of soulmates?

Of course you do! And you can!

The following questions will tell you a lot about their perspective and experience when it comes to love and romance:

What’s the most romantic thing you’ve ever done for someone?

What are the reasons for your past break-ups?

Have you ever been truly in love?

What did you think of me the first time we met?

What would your perfect date night look like?

Do you believe in the idea of soulmates?

What do you think is the most important thing in a relationship?

What qualities are most important to you in a potential partner?

What is your thinking on the concept of love at first sight?

11. Life experiences

Life experiences have the power of shaping us into the person we are today and every person has their own unique story to tell and so does your crush.

I’m sure you can’t wait to know everything about what they’ve been through because you perceive them as an enigma and every detail about them would help you solve the mystery.

In order to find more about their life experiences, you can ask these questions:

What is the best thing that has happened to you so far?

What is the worst thing that has happened to you so far?

How many times have you been disappointed in life or people (and why)?

Have you ever felt like giving up on something huge you started doing but then didn’t and now you’re glad that you didn’t?

How do you deal with annoying people?

How do you cope with stressful situations?

What is the biggest lesson you’ve learned in life?

Who is your idol and who or what is your biggest motivation in life?

12. First date experience

I bet there’s nothing in the world you would ever want more than to find out whether your crush is the romantic type and what kind of dates they prefer.

And it would be really awkward to ask directly about all that, so the best bet is to simply ask a few questions about their first date experience:

When did you go on your first date?

Where did you go on your first date?

What would you do differently if you could?

What is the one thing you liked most regarding your first date?

Did you enjoy it?

What are some romantic gestures that you remember doing on your first date?

13. Free time

If you want to learn more about your crush’s personality and the things they are passionate about, then ask them about their free time:

What do you usually do in your free time?

How much free time do you have?

Is there something you wish you had more free time for?

Based on their answers, you can start creating a mosaic of their personality in your head.

Also, let’s say they’re jogging or doing the same activity as you in their free time and you realize that you share the same passion about certain things.

You’re immediately one step ahead of the game and you can easily arrange to meet somewhere and join up to do the activity together!

14. Music

I personally am a huge fan of music and if someone asked me about it, I would literally kiss his feet.

Now, regardless of whether your crush is a huge fan of music or not, talking about music is a fun thing to do.

And it can also tell you a lot about their personality and if you share the same tastes in music!

For example, I’m a rock lover and here where I live, there are not so many rock lovers, so when I meet someone who has the same tastes in music as me, I start praising the Lord and heavens.

Music is not only music; it is a set of principles, perspectives, lifestyle and much more.

So, to find out to which crew your crush belongs, consider asking the following questions:

What kind of music do you prefer?

Do you have a favorite band/singer/album?

Have you been to any concerts recently or do you plan to?

Do you have a song that has been set as an alarm for some time and now you couldn’t hate it more?

What kind of music don’t you like and why?

To what degree has music influenced your life?

If you could go to any concert in the world now, which band/singer would you choose (and with whom would you go)?

Do you judge people by the type of music they prefer?

Have you ever tried playing an instrument or do you have a wish to learn to play a certain instrument?

Do you have any musical talents?

Have you ever written a song for someone?

See also: 50 Questions To Ask Your Crush And Help Them Open Up To You

15. Movies, TV shows…

Is there anything more exciting than talking about inspiring movies that have literally changed your perspective on certain things, about comedies that have made you laugh like there’s no tomorrow or about those contagious TV shows that you just can’t stop rewatching?

I bet there isn’t!

So, if you’re running out of things to talk about with your crush or you want to spice up your conversation, you should definitely mention your favorite movies and TV shows.

Also, you want to know whether you have the same or at least similar taste when it comes to these things, so that you can watch or rewatch some things together while curled up next to each other or while holding hands in a movie theater. (It’s the best feeling in the world.)

As with music, you can ask similar questions:

What genre/type of movies do you prefer?

What’s your all-time favorite movie?

Do you have a favorite actor/actress/director?

What was the last awesome movie you saw?

When was the last time you went to the movies?

What’s your favorite TV show?

How many movies and TV shows have you rewatched more than three times?

What’s your favorite quote from a movie or a TV show?

What was the reason for the last time you cried during a movie?

16. Food

Given that couples spend half of their time eating while watching Netflix or something, visiting restaurants and eating some more in a movie theater, food has become an important aspect of dating and relationships.

And I know that you’re probably dying to know what kind of food your crush enjoys.

And did you know that you can actually reveal a lot about your crush’s personality according to the type of food they prefer and their way of eating?

For example, people who prefer spicy food are known as being extremely passionate and those who eat fast are known to be selfish in bed.

There are also people to whom food is too much of a priority. So you would want to know whether all this applies to your crush as well!

By asking the following things, you’ll find out what kind of food your crush likes and how it accentuates their personality:

What’s your favorite food/restaurant?

Do you like cooking?

What is the weirdest food you’ve ever tried?

Are you a fan of spicy food?

Are you a slow or fast eater?

What is your favorite ice cream flavor?

What is one snack that you must have when watching movies?

17. The meaning of life

If you’re a fan of deep, inspiring topics, then you should definitely suggest talking about the meaning of life.

You will show your crush your unique perspectives and they will share their own views with you as well.

Knowing what life means to them will help you learn what kind of person they really are.

If life means so much more to them instead of only going out, going to work, to the movies and similar, then you know they’re living their life to the fullest and not taking any moment for granted.

Ask the following questions and learn whether they embrace the little things in life instead of only chasing artificial ideals like the majority of people today:

What does life mean to you?

Do you like spending time in nature?

According to you, what is the measure of happiness?

Have you found your life purpose?

If you could change the world today, what would you change?

Would you rather be poor and happy or wealthy and sad?

When was the last time you smelled a flower or admired little things that most people usually don’t pay attention to?

See also: This Is What Life Means To Me

18. Books

If you’re a book lover, you would definitely want your crush to suggest to you a few inspiring books so that you can broaden your horizons (and you would want to know what to give them for their next birthday):

Are you a book lover?

What types of books do you prefer?

What was the last book you read?

Do you have a favorite book?

Are there any books you would recommend I read?

19. Hobbies

Hobbies are an important part of every individual’s personality and daily life because it’s something that they’re passionate about and something that means a lot to them.

And just like books, movies and music, hobbies can also reveal a lot about your crush’s personality as well:

Do you have any hobbies?

When did you start doing them?

How did you get started?

Do other people judge or support your hobbies?

What hobbies did you have when you were a child?

If you could do your hobby for a living, which one would you choose?

20. Tech topics

Tech has become an inevitable part of our life, relationships and every other aspect.

And when it comes to your crush, you need to know what social media platform they prefer (so that you can add them), whether they play games and on which websites they spend most of their time:

What’s your favorite app on your phone?

What app do you spend the most time on?

Is there any app you wish you didn’t have to use?

What is the longest you’ve been offline?

Are you a casual or hardcore gamer?

Is there any game on your phone or tablet that you’re really into now?

What would be the most useful thing you could do with virtual reality?

How many phones have you lost or broken so far?

Which social media platform do you spend the most time on?

Who is the most interesting person you follow on Instagram?

What kinds of people do you follow on social media?

Is there someone who sometimes annoys you but you still follow them?

Have you ever blocked or ignored someone who annoyed you on social media?

21. Current trends

In this world, we have two kinds of people: those who follow trends and those who dictate trends and avoid following the crowd.

If you want to know which one your crush belongs to, consider asking the following questions:

What are some current trends you’re totally into?

Do you usually follow trends or just do your own thing?

Do you care about what other people will think about your choice of outfit and similar?

What current trend would you ban?

22. Life goals

By asking your crush about their life goals, you’ll learn a lot about their character, whether they’re ambitious or strong-willed and whether they have big dreams.

This will also tell you if you’re compatible because you certainly don’t want to be with someone who is a couch potato and whose biggest accomplishment in life is eating a bag of chips or drinking a liter of beer in ten seconds.

You can first start by asking them about their short-term goals and then switch to long-term goals and in that way, the transition between questions will be smooth.

You will not scare them away by suddenly diving too deep into their personal space and their plans for the future because not all of us are eager to share our plans with others.

Fun Things To Talk About With Your Crush

To win the heart of your crush and spice up your conversation, it’s important to include a few fun topics as well.

And lucky you, there are tons of fun convo topics that will accentuate your sense of humor and let your crush see what a chill and relaxed person you are!

And everyone likes to hang out with such people, right?

So, let’s see:

23. Pet peeves

I don’t think there is anything more hilarious in the world than talking about pet peeves. I mean, every person has them.

In case you’re not familiar with the concept, pet peeves are those things a particular person finds especially annoying and these things are usually hilarious because every person has their unique pet peeves.

My biggest pet peeves are chewing with your mouth open, when some things are not left in a certain position and so on.

Sharing yours with your crush will make them laugh their ass off and vice versa, so keep in mind to mention them!

24. Funny childhood memories

Childhood is one of the funniest times of all because a child’s world is full of excitement, freedom and crazy things that annoy every parent.

And when we grow up, all we have left from our childhood is our funny childhood memories.

So, why not share them with your crush and make them laugh as well?

Show your crush what a wonderful and fun childhood you had and I’m sure they’ll be willing to share their own with you as well.

Funny childhood memories will bring tears to your eyes and connect you on a deeper level because you will feel as if you’re reliving it again with them.

25. Embarrassing moments

We all have a map of embarrassing moments in our head that we want to forget and erase from other people’s minds if they’ve witnessed them.

But still, we have to admit that those embarrassing moments are the biggest source of laughter in our life and in the lives of our close friends.

Talking about your embarrassing moments, like entering the wrong car, saying something insulting in front of your boss, farting or over in public or texting the wrong person will surely lighten up and spice up your conversation.

Your crush and you will enjoy every single second of it, so why not share it with them, no matter how embarrassed you are?

You know what they say: sharing is caring!

26. Hilarious Wi-Fi names and passwords

I can’t remember how many times I almost died laughing once I connected to someone’s Wi-Fi.

Funny Wi-Fi names and passwords have become a real tech trend!

Now, let me tell you about my funny experience.

When I got home from where I was studying, I realized that my family had changed the password because I couldn’t connect to the Internet.

So, I asked my father to give me the password and he said: Ask Tomislav (my brother).

I was like, okay, I will go and ask my brother Tomislav because apparently he knows the password.

I said to him: When I asked Father about the password, he said: Ask Tomislav. So, what’s the password?

Brother: That’s the password.

In case you haven’t understood, the password was: Ask Tomislav!

Yep. I don’t even want to think about how many people they’ve pranked so far with it. Pretty witty, I must admit.

I’m sure you and your crush have similar experiences with your Wi-Fi names and passwords, so make sure to check your phone and tell each other a few funny names and passwords for the sake of a good laugh!

See also: 22 Signs He Has A Secret Crush On You

27. Funny proposal

If you’ve ever witnessed a proposal with your family and close friends, then you probably know what I’m talking about.

Funny proposals are real gold when it comes to laughing your ass off and if you’ve been a part of one, then you have plenty of material to retell to your crush.

However, don’t forget to also ask them about their experience regarding funny proposals in their circle of family and friends.

Another thing that you can do is ask them to come up with their own idea of a funny proposal to see how creative and romantic they are.

(It might not be a perfect proposal but it will surely make you laugh hard.)

The last funny proposal I saw online was epic. A couple was at a movie theater watching an animated movie and in the middle of the movie, the faces of two characters changed into theirs and they were about to kiss.

The girl was shocked, looking at her guy and wondering ‘What sorcery is this?’

And then, he kneeled and proposed to her!

It also turned out that people in the movie theatre were their family and friends. Yup, a lot of plot twists!

28. Funny memes and videos

In the era of advanced technology, there isn’t a single person who hasn’t found at least one funny video and who hasn’t been sent at least one funny meme.

Funny memes and videos are, without a doubt, some of the funniest things that you can find on the Internet today, so why not use them to your advantage when it comes to winning your crush?

Retell them or show them a few funny videos that you’ve seen lately and send them a few funny memes when texting them.

And ask them to do the same. As a matter of fact, you won’t even have to ask them because who doesn’t like to talk about funny things, especially when it comes to funny memes and videos? (That’s what I thought.)

Random Things To Talk About With Your Crush

When it comes to establishing a perfect convo with your crush, you need to pay attention to balancing things.

That means you should never only focus on only one thing like personal things.

Remember to keep things exciting by adding variation. And the following random topics are just perfect for that:

29. Holidays

What are your favorite kind of holidays and why?

What were your favorite holidays when you were a child?

Do you have any plans for an upcoming holiday?

30. Aliens

Do you think aliens exist?

Do you think they’ve already visited us?

Do you think that aliens are more intelligent than us humans?

What would you do if there was an alien invasion?

What would you do if aliens abducted you?

31. Habits

What would be your best / worst habit?

Have you ever succeeded in breaking a bad habit and what was it?

Do you have a bad habit that you just can’t seem to break no matter how hard you try?

32. Online dating

Have you ever tried a dating site or app? How did you like it?

Do you prefer online / app dating or more traditional ways of dating?

According to you, what are some pros and cons of online dating?

33. Drinking

What’s your favorite drink/alcoholic beverage?

Do you prefer going out or having your friends over when drinking?

Beer or cocktails?

Have you ever been drunk to the extent of losing consciousness?

34. Sleep

Do you have trouble falling asleep or do you always sleep like a baby?

Do you have a secret to getting a good night’s sleep?

What’s the longest you’ve gone without sleeping and what’s the longest you’ve slept?

35. Art

Are you an artistic person?

What kind of art do you like?

Do you have a favorite artist?

Have you ever visited art museums?

What is your opinion on modern art?

What is the coolest piece of art you’ve seen?

How would you describe the influence of art on our daily lives?

In Conclusion

As you can see, there are many interesting things to talk about with your crush and all you need to do is pick one or a few, gather up the courage and start a conversation with your crush.

If you don’t know them yet, use the above conversation starters that are guaranteed to prolong the conversation and help you get to the next level.

After that, you can mix interesting topics, fun topics and random topics to show them what a creative and inspiring person you truly are.

Just make sure to maintain eye contact during the conversation, listen to them carefully when they’re talking and be creative when giving your own answers.

If you apply all this, I can guarantee you that you’ll win them over in no time!

Good luck!

See also: Does My Crush Like Me? This Is How You’ll Know For Sure!