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How to Text a Girl and Keep it Interesting

Have you been pondering for ten minutes about what you can write to your crush? Well you have made the right choice and arrived here! In this guide, I am going to give you 100 practical examples of messages you can send to your dream girl through WhatsApp, Facebook Messenger, or any other messaging platform you might use.

How to text a girl and keep it interesting

Hello, I’m Frankie Caruso and I welcome you to my blog.

The idea of making a guide to help those discover what messages to write (and topics to talk about) to a girl, came from multiple questions that I was asked after I created an article called 10 tips to get a girl on WhatsApp.

Here are some examples:


Frankie, I like this girl but I don’t know how to start a conversation with her. Please help.


Frankie, I just started dating this girl and I don’t know what to write. I don’t want to lose her. What questions should I ask?


I want to have a chat with a girl in my college, but she has no idea who I am. How do I get started?


What questions can I ask a girl so I don’t look stupid? What questions is she sure to answer? Thanks.

This list could continue for a while…

But I tell you now, Brother I speak the truth! Have you ever asked yourself one of these questions? If you are here, the answer is likely yes.

First off, I want to tell you that you should not feel stupid because you don’t know what the right to a girl. It is actually a very common problem, especially when it is a girl that you really like. It is normal to fear making a mistake.

Unfortunately, in this digital age, knowing what to say to a girl in a chat is pretty fundamental for the earliest stages of dating. Most of the interactions that occur these days happen through chat, SMS, messages, and various social media platforms.

As I stated earlier, I intend to give you practical examples of phrases and messages that you can write to a girl in one of these chats. This will include the very first message, and even step into more complicated correspondence like asking her out.

I simplified this guide by breaking it down into more digestible topics:

  • The First Message (Starting the Conversation)
  • Best Questions to Ask
  • Questions to Get to Know Her Better
  • Flirting Messages
  • Romantic Messages
  • Friendly Messages
  • Serious Messages

Ready to get started?

Let’s go!


Frankie’s Take:

You can feel free to copy and paste the phrases from these later lists that suit the conversations you were trying to have. These questions work on any messaging app, including both WhatsApp and Facebook Messenger.

The First Message (Conversation Starters)

The First Message

The first message is always the most difficult to send. You don’t get a second chance at a first impression, and the fear of making a mistake or saying something stupid and never getting reply is a significant stress.

But not to worry, as I always say: never miss an opportunity.

So be brave and throw yourself out there.

Within this section, I collected 15 questions that you could ask a girl via text to start a conversation. These are questions I’ve personally tested and know to work 100% of the time.

These conversation starters should actually be the second message that you send. It is always best to begin your conversation by merely saying hello with her name. For example, “Hi Natalie.

Ready to get started? Good.

1 – What’s the best thing that happened to you today?

This is a very good alternative to asking what someone did. It already starts out your conversation on a positive tone.

2 – What’s the scariest situation you’ve ever experienced?

there’s no doubt that everyone has had a situation that has scared them, or some circumstance that made us almost piss our pants. this is a good opportunity to share your experience and hear hers, hopefully starting a longer conversation.

3 – What’s something weird that you find attractive in a person?

Initially, this question might seem pushy, but it isn’t. In fact, many girls find it funny. As well as hoping you find out what she finds attractive, it allows you to get to know her a little better at the same time.

4 – What was your favorite show when you were a kid?

In a way, this is an easy way to segue into your current favorite shows, something that can allow you to find some common ground.

5 – If you could change your life with any celebrity, which would it be?

This actually allows you to do several follow up questions that keeps her engaged in the conversation. Some examples maybe: Would you feel comfortable being stalked by paparazzi? What would you do with all the money?  As you can see, there are many approaches that you could use.

6 – What is the first thing that you would do if you won the lottery?

You will find that a question like this can actually take you on a rather lengthy conversation, but also divulge many of her interests at the same time.

7 – Do you have any favorite songs on Spotify/iTunes/YouTube etc?

You can ask her if she will share them with you or let you listen to some. You might find that there are some things that you both enjoy.

8 – Did you do any after school activities in high school?

Being involved in after school activities can share common interests, and is a way to make connections aside from school.

9 – If you could live anywhere in the world, where would it be?

This gives you an idea of where she sees herself in the future, her current interests, and allows you some very interesting lead-in secondary questions, such as: Japan for its food? Italy for its art? Australia because it has kangaroos?

10 – Do you have a favorite place to have lunch?

You should really pay attention to the answer here, because when you ask her out, you already know someplace that she likes to eat.

11 – What is the craziest thing that you’ve ever eaten?

This is an intriguing question that can open up a lengthier conversation, especially when you both have things to share. You also have the possibility of follow-up questions including what it tasted like, why it was eaten, and if they would do it again.

12 – How frequently would you say you try new things?

Actively search for any new and exciting experiences that help her to grow.

13 – What is the maximum distance that you could reach with a paper plane?

This is a question designed to initially make her laugh. If a girl is laughing, you are on the right track. Challenge her to an airplane race where each contestant gets a dollar bill. Whoever flies the airplane the farthest gets to keep both dollars. It’s a fun little game that puts you in a good light, makes you seem fun, and allows you to spend some physical time with her.

14 – What would you say is the best part about being a woman?

This allows you to inadvertently introduce sex into your conversation.

15 – Do you know any songs by heart?

Listening to a song with somebody is always a nice way to spend some time. Listening to the songs that she knows by heart allows you to get to know her better without being overly pushy.

The Best Questions to Ask the Girl You Like

Best Questions to Ask a girl

This section is all about the realest questions. These are foolproof strategies. I won’t lie, at first I didn’t want to share then with anyone, but then I said to myself: why wouldn’t I want to help my readers?


Frankie’s Take:

These are the questions that can compel the girl you like to think long and hard. Don’t be scared if you do not get an answer immediately.

But enough chitchat, let’s get right into the meat…

16 – When was your last pleasurable experience?

Was it her eating a container of Häagen-Dazs ice cream all by herself? Was it the last time she ran through a wheat field? Don’t just have her tell you, have her explain the experience.

17 – Do you have an unexplored secret passion that many people do not know about?

It might be a good door opener to help her follow through on some of her passions. Perhaps she wants to learn how to paint. this might be a good excuse to try one of those “Paint and Wine” evenings at a local establishment. You both get the fun of playing with paint and get a little tipsy on the wine.

18 – Do you prefer group dinners or one on one intimate meetings?

Once you have that answer, you have an open door to ask her to dinner with her friends or to take her out to dinner by herself.

19 – What is the strangest situation that you’ve ever been in?

For your sake, let’s hope she hasn’t seen her parents having sex lol. I’m kidding of course, but it is a good question that can start a long conversation.

20 – Is there a place that you usually go for inspiration? Why is that?

If the girl you like enjoys traveling, hiking, or just taking long walks, this question might just amaze her.

21 – Do you have a favorite seasoning?

You are quickly going to find out if she is somebody that puts ketchup on everything that she eats. Beware.

22 – Do you have a story that you like to tell the most?

We all have a certain story or two that have left the mark on us in a very positive way, or might just be really funny to share. Let her tell you one of those stories, and then respond with your own.

23 – Is there something that he would regret not doing or trying in your life?

There are plenty of things that can end up on a bucket list, including seeing an eclipse, experiencing the Northern Lights, or traveling to Paris. Try to be engaged in her responses to encourage her that anything is possible in her life.

24 – What was the last book that you really liked?

This is a pretty good way to find out if you have similar literary tastes. However, if neither of you is a reader, audiobooks are not too different. I myself listen to audiobooks all the time when I’m making dinner.

25 – If you had to choose one, which of your five senses would you prefer to lose?

You can discuss each of these individually, though some will yield longer conversations than others.

26 – What do you consider your greatest achievement so far? What would you like your greatest accomplishment to be for your whole life?

You might also take the moment to ask her what she’s most proud of. One of the keys to getting a girl and having a positive relationship is supporting their interests and goals. Helping her and encouraging her to achieve these goals makes you a valuable part of her life.

27 – What do you have in your purse right now?

While you should never be the one to go through a woman’s purse, this is a question that can catch her by surprise in a positive way. And, you can learn some of the secrets of her daily life.

28 – Where and when did you see the most beautiful sunset?

Watching the sunset or rise are unique experiences that each of us can remember.

Asking her what the most beautiful sunrise or son said that she’s seen it gives you an image of a hopeless romantic. Girls just love that.

29 – What’s the worst place that you’ve been trapped for a long time?

Airports are in nightmare when your flight gets delayed or canceled, for example. ask her what situations would make her go crazy.

Questions to Get to Know Her Better

Questions to Get to Know Her Better

Have you gotten past the introductions and know you are ready to get to know her a little better? Have you now become curious about her passions, hobbies, and interests?

It is important to keep the conversation rolling if you broke the ice.

I have put together a list of targeted questions that keep you in a positive light, and keep her talking as well.

And here they are!

30 – What is a cause that you feel close to?

If she is volunteering or devoting her time to something she considers important, it might be something you guys can do together. Talk about a memorable first date for her.

This strategy is great because you get to help out someone or something in need, you meet new people, and it’s a free way to make you look caring and compassionate.

31 – Are there any circumstances where you feel shy?

If you keep this information in mind when you’re with her, you can do more to make her feel comfortable in situations where she would not be. She will realize this as it’s happening and appreciate it.

32 – Is there a special talent or skill that you’ve always wanted to have?

Learning something new can be both challenging and daunting, but it’s a lot easier if somebody is helping you to persevere.

Show that you are willing to help her get started and stick with it.

33 – Which of your family members do you most admire and why?

Let’s have for your sake that she has a family member that she admires at all.

This is a good exploratory question to learn about both her family life and her childhood.

34 – What is your best talent?

You would assume that there is at least one thing that she’s proud of. Ask her what this is, and give her an opportunity to demonstrate.

35 – What made you choose (the current University she is attending)?

This conversation could go in multiple directions, but can give you an idea of her general interests.

36 – What is the most beautiful or traumatic thing that happened to you on a date?

and it’s no great surprise that she likely has a bad history of dating, as you likely do as well. And it’s always good to look back and laugh at times.

37 – Does your family have a strange tradition?

This is a question that can get you a foot in the door about her family life without feeling invasive.

38 – Have you ever had your future predicted by a psychic? If so, what did they tell you?

No matter what you think about fortunetellers or tarot cards, they can be a lot of fun if not taken too seriously. This can also be a chance opening for you to ask her out.

39 – Which event of your teenage years puts you to shame?

better explain some of the stories of these formative years of her life, even bringing out some pictures, and laugh together about your childhood mistakes.

40 – What is the best gift that you’ve ever received?

This is a casual way for you to find out if she prefers experiences or material goods as gifts.

41 – If you could change one thing about yourself, what would it be?

Improving yourself is the key to becoming a better human being. if she is always looking for ways to improve herself, you want to keep her close.

42 – Who was your best friend in elementary school?

We change as we grow, and it’s interesting to see the different paths that we have followed. Have her share with you not only who her best friend was during this time, but why and some of the things that they did.

43 – Do you still follow your friends’ advice?

Some people genuinely learn from their mistakes, while others prefer to follow advice they’ve received. Try to figure out which type of girl she is with this question.

44 – What good do you bring to the group when you hang out with your friends?

This is a question designed to help her see where she fits in with her group of friends. Is she the lonely one? Is she the leader of the group? Is she the fun one? Ask her these type of questions.

45 – Did you follow any specific trends when you were younger?

Introducing some nostalgia into the conversation it was a great way to connect and help her feel closer to you.

46 – What do you think lies in the dark?

This is a probing question because the darkness tends to hide our deepest fears. Find out what monsters haunt her at night.

Sometimes, the monsters aren’t really monsters at all.

47 – What’s your worst habit?

Be sure to share yours too, it is OK to be a little self-critical.

48 – What is something about you that might surprise your parents?

Another great question to make a conversation take a more sexual, hotter turn.

49 – What do you consider to be your weirdest problem?

Asking her about her issues is an ironic way that helps her open up and talk more openly about herself to you.

50 – When you talk about me to other people, what do you say?

Women tell their girlfriends everything – especially about the guys that they’re chatting up and hanging out with. Take a second to make sure that what she’s sharing are all the nice things.

51 – Do you have any nightmares? What happened in them?

This is a great opportunity to turn a serious topic into a joke. If you can make her laugh about things that have made her uncomfortable, you are well on your way to success.

Flirting Messages

Flirting Messages

As much as it might make you nervous, it’s time to start flirting with the girl that you like.

Pay close attention to the topics that you choose. If you are good at it and you play this situation well, the conversation might take a much hotter turn.

Here are some great topics for flirting with a girl over text.

52 – What is your guilty pleasure?

This is absolutely one of my favorite questions.

It often makes the girl think hard about how to answer. In fact, if she does not have an immediate response you should not worry. Give her time to think about it don’t pressure her with more questions on top of the one.

53 – When was the last time that you stayed up all night?

Everyone at some point in their life has stayed awake all night. Let her tell you about the experience, and if you are skilled, you can direct this conversation towards something hotter.

54 – If I asked you to dress sexy, what would you wear?

Most girls are vain enough to want to talk about themselves constantly. Talking about their outfits and clothes will make her feel more comfortable.

55 – What is the first thing that you look at in a guy?

This helps you to understand what attracts her both physically and intellectually.

56 – How would you define a good sexual relationship?

My definition: a relationship with a LOT of communication, mutual desire to satisfy the other person, and openness. If these things are not present, problems are bound to emerge.

If you tell her this, she is going to fall in love with you.

57 – Would you stay with me if you found out that… I had a criminal record?

If you take a moment to pretend that you’re a serial killer or something equally ridiculous, you’re sure to make her laugh.

58 – Can you describe your idea of a perfect night together?

Take notes here. In the future, you will want to organize this evening exactly how she described it.

59 – When did you lose your virginity? How did that happen?

Your first time is something special. It is OK to look back on it with some tenderness and talk about it with other people. There’s nothing wrong with this conversation even if the experience wasn’t the best.

60 – What do you fantasize about?

Do you have a particular fantasy that you’d like to make come true?

61 – What is the first thing that you would do if you were the opposite sex for one whole day?

Obviously, her answer will be something like swing her penis like a helicopter. Isn’t that what all guys do every morning when they get up?

62 – If you were a ghost for just one day, what is the first thing that you would do?

Basically, this question is more about being given the gift of invisibility. Have her tell you what she would do if she were invisible for a day.

Romantic Questions

Romantic Questions

Here is a secret that almost everyone knows: girls are into romantic boys. There is a line however. You can get too sappy.

To avoid making this mistake, I prepared some questions that should help you to navigate this conversation in text with the girl that you like.

63 – How important is marriage to you?

Once you find out this you can also ask neighboring questions like the importance of children and family. Do you find out when in her life she hopes to have them.

64 – What do you like most about me?

If she is maintained a chat with you, there’s definitely something that she likes about you. There’s nothing wrong with asking her what her favorite things are when it comes to you.

65 – What can I do to make you understand that I really like you?

Make sure you pay close attention to her answer and never forget to give her some sincere praise for being honest with you.

66 – Is there anything that you would like to tell me?

You can help smooth this over by first sharing something that you’ve never told anyone.

67 – Do you think you still have feelings for someone in your past?

Honestly, you never forget your first love. Don’t get too jealous if she says yes. Talk about it with her. It is actually a great opening to a deep conversation.

68 – What about me is attractive to you?

Perhaps at first, she thought you were a bit silly, but gradually it started to grow into deeper feelings.

69 – If you could change something about me, what would it be?

You need to remember not to take the answer personally. If she is honest enough to share something with you, then you should remember that change is necessary to overall improvement.

70 – How would you define love?

To love is to live. This is a little tip so that you can answer if you find yourself tongue-tied and unable to define it for yourself.

71 – Is there anything in particular that you don’t know about me that you would like to?

There’s probably something she’s been dying to ask you, but she’s been too nervous to do it. Open up now and answer truthfully.

72 – If you are sad or angry, how would you like it to be treated? More specifically, what makes you feel like somebody is actually taking care of you?

You can impress her here by really focusing on her emotions.

73 – What are some of the most truly romantic dates? What are some sexy ones?

Everyone has a different idea of romance. Going to a sex shop and finding new toys is 100% worth it. Also, I heard the strip club can put you in a good mood for the rest of the night if you’re into that sort of thing.

74 – What gourmet restaurant have you always wanted to try? Do you have a homemade food that you adore?

Spare a bit and surprise her with a couple of dishes that you cannot normally afford or that you’ve never tried. Set up a candlelit dinner for her.

Honestly, you CANNOT go wrong here unless you burn something down.

75 – Do you believe in marriage? Or do you prefer just staying in a serious relationship?

You can learn a lot about the type of girl she is with this question.

Funny Questions

Funny Questions to ask to the girl like you

If there is one thing that I have learned in my 30 years, it is that the way to a woman’s heart is through her laughter.

You do not have to be handsome like Brad Pitt. You can be ugly like Chewbacca – you just have to make her laugh.

That’s great advice and all you say, but how can I do that?

Just start sending her nice messages that can put her in a positive mood, like some of these:

76 – What is your favorite video or GIF that makes you laugh?

It is possible that she has already shown you some of her favorite ones by now.

78 – What is your favorite joke?

Q: How much tickling does it take to make an octopus laugh?

A: Tentacles!

Q: Where does a king keep his armies?

A: Up his sleevies!

Silly, stupid – but sure to make her chuckle.

78 – What is the (cutest/most shocking/weirdest/etc.) message you have ever received?

If it was strange enough, she’s probably already got a screenshot of it. Ask her to show it to you.

79 – What is the best picture that you feel you’ve ever taken?

If you need an example, you can always send a picture of her for extra bonus points.

80 – What’s the worst message that you sent by mistake?

Everyone has sent one of these types of messages by mistake.

Allow her to explain this experience and make sure that you don’t miss opportunities to tastefully rib her.

81 – What would you really like to buy right now?

Start this discussion as a playful hypothetical, but try to remember it as something you might consider giving her on your first date.

82 – What is the nicest thing you can buy on the Internet?

For one, there’s a Donald Trump inflatable doll. Imagine her laughing if you tried to give that to her.

83 – What silly phrases do you know for flirting?

Did it hurt?

What, when I fell from the sky?

No, when you fell down the stairs the other day.

Now, I told my girlfriend this, and though it was not accepted greatly, we both laughed like idiots. Mission accomplished.

84 – What strange/useless talent do you have?

We all have some talents – some are incredibly useful while others are utterly useless.

Serious Questions

Beyond being funny and likable, you also have to show that you are a deep and serious person as well.

This will keep the girl interested.

I can help you with some interesting topics that you can use during your longer conversations.

85 – What is it that is not real, but you desperately wish would be?

Some examples might be hidden places.

86 – What’s the smell that brings you good memories?

Perfumes and other aromas can take us back in time. What are your favorite scents from your past? Find them and share them so these smells are now connected with you.

87 – What are you best at?

She is likely to have skills of her own and she will appreciate that you’ve taken an interest in them.

88 – What makes you nervous?

For some people it is crowds or absolute silence, but we all have something that makes us uncomfortable. Ask her how you can help her feel more comfortable when she gets nervous.

89 – Are there needs in your life that have not been fulfilled? Is there anything I can do to help you?

Every one of us has different needs. If it is OK with her, help her with what she needs. If she likes you, she will want to do the same. Just don’t be clingy.

Questions to Ask Your Girlfriend About You


So far, I have shown you questions for the girl that you like. But what if you’re already dating this girl?

I have been thinking a lot about that too, so I decided to select some questions that you can ask to keep the conversation going with your girlfriend. As usual, you can copy and paste them into whatever messaging app that you use to chat with her.

90 – If you could change one thing about yourself, what would it be?

If it is something about herself that she can change, offer your help in creating a plan and putting it into action.

91 – Did you feel closer to your mom or your dad when you were growing up?

Our parents always have a favorite child, so naturally, we can have a favorite parent too.

92 – Who do you trust the most?

This might divulge who your girlfriend’s best friend in the world is.

93 – Have you ever left someone you still love?

There are many instances that you have to leave a relationship because it is unhealthy.

Be as nice as you can be, and hope that she does not have to do this to you.

94 – When was the last time you were really disappointed?

Have you been in a bad mood lately? Has the moment passed or is there something I can still do to help?

95 – When was the last time that you failed at something?

Be understanding and work hard to find a positive aspect of the story.

96 – What is it that always makes you smile?

What is a consistent something that always brightens your day.

97 – If you could up and change jobs without worrying about money, what would you rather be doing?

It does not have to be some crazy change. You can always keep you day job and devote some of your free time to your passions. For example, like I do with my blog.

98 – Which of your past relationships have made you happiest? Why did they end?

Many people might tell you it’s a bad idea to talk about someone’s exes. I disagree. You can learn a lot from the most things her exes made and not make them yourself.

99 – Have you ever forgiven yourself for bad things that you did?

Everyone is done something that they regret. We have to forgive ourselves if we want to move on and lead happier lives.

100 – In the ideal intimate relationship? How often would you have sexual relations?

Communicate your own needs and find the happy medium you both can agree on.

Bonus: Starting a Conversation with the Girl You Like: 4 Great Tips

In recent years, I’ve had the chance to have many long talks with you on my Instagram profile. (@carusino – follow me if you like!)

I have found that there are fears common to everyone approaching a girl for the first time. You might fear not knowing how to manage the situation, a fear of being dumped, or a fear of not knowing what to say.

That is why I have decided as a bonus to throw out these 4 tips:

Tip #1: Relax

If she is texting you back, some part of her is attracted to you. It is easy to give loss the negative thoughts. Instead, let things happen naturally.

Tip #2: Listen

Really pay attention and don’t forget what she says. Girls like to tell their feelings, how they spent their day, etc. If you really like her, she deserves your full attention.

Tip #3: Ask the Right Questions

I might have already provided you with a virtually endless list of questions here, but you should take the opportunity to probe each of these more deeply. Show her that you’re really listening and are interested in what she has to say.

Tip #4: Be Yourself and Try to Have Fun

You know you don’t want to lose her. If you are hiding your real self, she’s going to find that out eventually.


OK, we have finally come to the end of this gigantic guide.

I’m not going to hide that I’ve worked a long time on it, and that it has not been easy to put together. In the end I am happy because I know this will help you.

Before we say goodbye, let me briefly recap the types of questions that you can find on this list.

First, I have included several icebreaking phrases. I would consider these the first messages you would send to a girl that you like.

I then put together the best 20 questions that you can ask a girl that makes a good first impression.

And the third part, you find a section devoted to personal questions to help you get to know the girl better. These help you gain her trust.

In the fourth part, I picked 10 questions devoted exclusively to flirting. Flirting with a girl is very important because that is the direct way to show her you’re interested.

The fifth section shows you some romantic questions. These are the questions you can ask if you’ve already dated her (or started dating her recently), or if you have not had the chance yet. Girls enjoy seeing a romantic side.

Sections six and seven are dedicated to fun and serious topics that keep the conversation going.

Finally, I took a moment to give you 4 tips that should help you through this whole process:

  • Relax
  • Listen
  • Ask the Right Questions
  • Be Yourself

That’s really it.

Come back and see me – I will anxiously await some feedback on how these questions worked for you.

A big hug (and a bit of luck),

PS – Here are some tips to bring the conversation out of messaging apps and get a real date.

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About Frankie Caruso

I'm Frankie Caruso. I'm a professional amateur in that ugly business of social media, instant messaging apps and computer security. I help all those frustrated people who call themselves digital illiterates to understand something about this confusing digital world.