Online Dating: What to Talk about to Keep Her Interested

Written by Ryan Cross

What to talk about on online dating apps – you could ask. In the modern online dating environment, attractive guys and girls are getting messages all day, every day from potential dating partners. That’s why outstanding texting skills and great conversations are often necessary to build trust and familiarity and eventually convince prospective dating partners to go out with you on a date. 

The following 20 interesting conversation topics will help you engage others in exciting and intense interactions, increasing your chances to go on a date with them.


Online Dating – What to talk about? – 20 Exciting Topics


School memories

Coming up with childhood memories is a great way to open up to each other and build up familiarity and trust. Hilarious, exciting, and even awkward stories from the school years make every conversation fun because everyone loves to discuss 

  • events that happened in school and affected their adulthood, 
  • lessons from others that they didn’t understand that time, but they do today,
  • and emotions that they felt about their classmates, teachers, and classes.


Who was your favorite teacher in elementary school / high school, and why? Who was the teacher who hated you, and why?

Have you dated someone or been in love in high school?

What was the funniest / most awkward / mindblowing thing that happened to you in high school?


Worst Dates

‘Worst dates’ is a fun topic, and discussing dating failures can tell you a lot about the other one’s personality and values. You can get to know each other better and figure out whether he or she aligns with your values and way of thinking. 


What was the most awkward date you ever had?

What do you hate the most about your dating partners?: If they arrive late, too needy or timid?

Have you ever met someone who was a pleasant surprise?

Have you ever met someone who looked completely different in photos?



Talking about goals and ambitions is an excellent way to discover many personality traits about your texting partner and share your qualities simultaneously. Girls love guys who are passionate about their goals because it gives a sense of confidence, grit, and purpose, indicating high status and attractiveness. Guys like girls who have future plans because these girls tend to be more intelligent and reliable.


What do you want to achieve in 1, 5, and 10 years?

What do you do for a living? Do you plan to stay at your current workplace for long?

What would you do if money didn’t matter?

What did you want to become when you were a child? Did you succeed?

What is more important to you? Friends and family or career and financial goals?


Your day

Talking about your day can also be an excellent conversation topic if you stay away from boring things. Even if your day was average, you can share your feelings and thoughts about otherwise mundane tasks like sending emails and showing up at corporate meetings. 


I always use elements from my daily schedule to enter a new – and more exciting – conversation topic with girls.

Habits, rituals, and superstitions

I consider myself a rational guy, but sometimes even I use different rituals to ensure everything’s going fine. For example, I always take the shoes on my left leg first because my idol soccer player did the same when I was a child, so I copied this ritual. I can also sleep at any time of day, which is also a fun fact about me that can be used to make convos more interesting.


Girls love to talk about zodiac signs and esoteric stuff. You can dive into these topics too, even if you don’t believe in them.



Books, series, music, and movies are infinite conversation sources. For example, texting about a new Netflix series can benefit you in different ways:

  • You can show the girl that you are a man of culture;
  • you can navigate the conversation towards the meeting by offering her to watch a new movie or to discuss a book together
  • you can get to know her better if you find out more about her taste in film and music


Your job

If you have an interesting job, work for a high prestige company, have a high-risk/high-responsibility career, or if you are an entrepreneur, then talking about your job is a must-have.


Talking about a career can be beneficial even for guys who work in a small accounting office that no one heard of. Always write about your job with passion. Include the purpose and ambitions about why you do what you do, and you are good to go.

Funny stories

One of my favorite funny stories is the one where I got into awkward situations. Girls are digging these stories because, first, we love to laugh at each others’ misery; secondly, women love guys who completely accept themselves and honestly share these accidents.

You can also tell about a funny joke you or your friend cracked the other day, funny accidents from misunderstanding, or some hilarious dating situation. Once, a girl said to me before our first date that she was wearing a long yellow coat. Of course, I went to the wrong girl.


Personal Values

Finding out others’ values is the best way to determine their personalities. Values are all the behaviors, ideas, skills, mindsets, and habits we find important to us.

Here are four questions that help to reveal your text partner’s core values:


“If you had to choose one thing worth living for, what would it be?

If this thing happened, what would it allow you to do?

If you achieved these with this thing, what would it make you feel?

Then this, and this is your core value!”



Talking about traveling portrays you as a culturally diverse person, which will get most people’s attention. We tend to associate adventurous personality, high status, and usually success with traveling; no wonder that talking about your trip to Cancun makes you more attractive.


Childhood experiences

You can learn a lot about someone by asking them about their childhood experiences. Moreover, you can develop a deeper bond with your texting partner by sharing these memories because talking about your childhood makes


What you wanted to be when you were a child, and how that changed?

What were the events in your childhood that determined your whole life? Who were the ones you looked up to and learned a lot from?

What were the things you thought worked one way but turned out to be very different?

What were your funniest memories?


Personal Boundaries

Boundaries are personal rules that we live by. We like others who respect our boundaries, and we are often pissed off when they cross them. Personal values and boundaries are pretty much aligned most of the time. For example, if someone thinks that respect is very important, then he or she might be mad at you if you are late for the date.


Conversations, where you talk about personal boundaries with potential date partners, can be pretty helpful: you can clarify what behavior you find inappropriate or rude and ask her about situations when someone crossed her boundaries. 


By asking these questions, you can become more conscious about how far you can go on your first date:


What was the most annoying thing you’ve experienced on your dates?

What are the three things that cut off every attraction if a guy does those? Mine are: poor hygiene, swearing and being late.


First impressions about each other

There’s a funny game I used to play with girls to get to know each other a little bit better. The game is called “You look like,” and it goes like this:

You form a statement about her based on her photos and what you already know about her. If you nailed it, the next turn is also yours; if you missed it, it’s her turn. That’s it.


This game is the perfect setting to get to know each other, flirt, compliment, and build trust and comfort.

Pro Tip: 

This game is about fun, so you can go completely off, like “you look like a girl who has more than ten teeth.”


You can increase your chances to meet her exponentially by playing other exciting games with her. Everyone loves games, and playing together builds up a more intimate relationship between the two of you.


Let’s play the “I would rather” game! If you were stuck on a deserted island, what would you save from the boat? A music instrument or pen and paper?


You can also play barchoba, where you think about anything, be it an object, an animal, or even abstract concepts like love, and the other has to find it out by asking questions. You can answer with either “yes” or “no”.



Involve her in your daily routine and ask her to recommend a fascinating book, a good movie, or a cool place to hang out.

Sometimes, I design logos, book covers, and websites, and I can tell girls love to tell their ideas on these things.


You can learn many personality traits about others if you ask for their opinions.

Offline and online dating

I’m a dating expert, so talking about dating and relationships is my second nature. You don’t have to know all the nitty-gritty details about attraction and desire in the online and offline dating environment. Share your experiences and thought about the topic and ask good questions.


Don’t you think that online dating made dating more difficult?

Do you like when someone approaches you on the street?

What was the funniest / most awkward online dating opening message you ever read?


Roleplaying is a powerful tool to navigate your texting partner into an imaginary world, painting an exciting view into her imagination. Roleplaying allows her to experience intimate emotions, no matter how fictional the story is.


In most cases, women (and men) go into the game. The roleplaying game encourages your texting partners to collaborate with you, in which they can imagine what it would be like to be with you in real life. Roleplaying also allows you to come up with sexual topics that would normally be inappropriate. 


Also, it takes you back to childhood, when roleplaying was part of our everyday lives. Believe me, these kinds of games are a lot more fun for adults than as a child: more experience, more imagination, and more determined goals.


Possible roleplaying topics:

  • Marriage
  • Bank robbing
  • Honeymoon
  • Saving the world
  • Apocalypse



It will blow your mind at how far you can go to build desire with texting. 

Your job with sexual topics is to create a world where the two of you are comfortable, where you can imagine anything. Women are very quickly get aroused by the explicit language. 


You’ll be shocked by all the dirty things and erotic language you’ll see if you pick up a romance novel from the bookshelves of a bookstore. For men, desire has a physical nature, whereas women experience it mainly on an intellectual and emotional level.


If you want to enter sexual waters, try to communicate in detail and color as possible. Create a more detailed picture in her mind. The more complex the story you share, the more you will be able to arouse her.


When you chat, you should be careful to describe your feelings and reactions like in books instead of objectively outlining reality.



Researches show that men and women find others physically and personally more appealing who flirt with them. We like to flirt, and we like to engage in conversations with someone who flirts with us.


Women are flirting addicts for the simple reason that it’s fun, and they can connect with guys on a more sentimental level by flirting with them. Flirting messages add a fun sexual ingredient to the online interactions and sparks excitement out of girls you text.


“It seems that I’m always smiling when I think about you.”


Your future date

At some point, you should invite your texting partner to hang out with you – otherwise, what’s the point of texting?

Bringing up the first date topic in a casual style makes her more comfortable with the thought that you will ask her out sooner or later.


Before I invite someone to go for a date, I often tease her about our future hangout. For example, you can text her that you would like to invite an authentic Mexican quartet to play music on the first date. If she plays along, then it’s a good sign that she would agree to meet you in person.