Technology has made it possible to meet anyone, anywhere, anytime! Apps like Tinder and Bumble connect us with matches nearby or even the opposite side of the world.

Page Contents

#1 Don't Appear Desperate
#2 Be Yourself
#3 Don't Write Essays
#4 Use Pictures, Emojis, and GIFs
#5 Flirt with Him
#6 Should you Sext Him?

I have used dating apps for the last 6 years or so in many different countries. I travel a lot, so I use these apps to connect with ladies.

Once connected, the chatting begins 😲. But chat can be awkward, especially in the beginning. With so much competition, you have to learn how to impress a boy on chat!

While we boys are simple creatures, texting can get complicated, confusing 🤔, and trying to impress a boy on a chat can seem difficult.

You don't have the advantage of a face-to-face encounter where you're able to read his reactions, figure out what he might be thinking or even if he seems into you.

But texting does have its advantages. For one, chatting before you meet allows you to get to know a boy. So, when you do meet, there is already some rapport between you.

Showing interest in a boy and having engaging conversations will help you improve your chances of impressing your crush.

#1 Don't Appear Desperate

Play it cool 😎, you don't have to reply to every text as soon as you receive it. Or ask a million questions as soon as you start chatting.

No one likes an overzealous stranger coming on stronger than hurricane Sandy.

The secret is to play hard to get while still keeping him interested. Boys don't like it too easy, they love a good chase 🏃‍♂️. If you try too hard, you'll come across desperate. Instead, you want to go for intriguing and mysterious 🧐.

This doesn't mean not replying, ladies! There is nothing more off-putting than a girl who doesn't respond or replies three days later ⏱.

Think about your replies and respond as if the person is sitting across from you at a table.

Another sign of desperation is being too agreeable. If you have a different point of view, share it. Don't just agree with what he is saying.

This leads me to point number 2.

#2 Be Yourself

This is so cheesy 🍕, and I hate saying it. But you have to be yourself. If you try too hard to please someone, you'll end up being something you're not.

If you think a boy won't like who you are. It will never work! Find someone else because you can't sustain being someone you're not.

Lying to impress someone will come back to bite you. Even small "white lies" will eventually get you into trouble. Don't exaggerate details or try to impress him.

Another part of being yourself is to allow the conversation to flow naturally. You don't have to be funny in every reply. Don't force humor, this can put someone off.

If you are naturally funny, then that's who you are and go for it. But if you're not usually a funny person, you don't have to be to please someone.

The most important thing is to answer questions he may ask and even pose questions to him. Boys don't expect you to be funny.

What really puts boys off is one or two-word replies where the conversation goes nowhere.

Show you're interested, ask him questions, and answer his questions as you would if you were chatting face-to-face.

#3 Don't Write Essays

Have you ever got a long text from someone, that seems more like a college application, rather than a text message? Annoying right? We all have those friends, and we never read those walls of text 📜.

Don't be that friend.

Keep your answers short but answer the question in full. You don't need to explain every point you make unless he asks, of course.

Short texts will keep your conversation flowing and keep him interested. Always leave him wanting more, and leave a little to the imagination.

If he wants to know more, he'll ask, then you can elaborate or explain in greater detail.

#4 Use Pictures, Emojis, and GIFs

Texting is the core of your communication, but you might want to mix things up with pictures, emojis 😉😘, and GIFs. If you're not naturally funny, this can help add a bit of humor to the conversation.

No matter how old you are, using emojis to express an emotion is always funny.


It's important not to overuse emojis and GIFs; or, they just become annoying. 🙄

Another great way to get a boy's attention is to share your favorite funny YouTube videos. Again, not too many, one a week is enough if you want to do this regularly.

Guys are not usually into cute cat videos, so look for people falling, funny accidents, and "slap cam" or "scare cam" videos. These types of videos are always a win with guys.

Don't share something you don't find funny yourself.

People can always tell if you're being fake about liking something. If you don't find it funny, don't share it just because you think he will.

#5 Flirt with Him

There is no better way to keep a boy interested than with a little flirting 😘. Not only is flirting fun, but it lets him know you're interested.

There is a fine line to flirting. The secret is to be subtle. Remember, guys love the chase, if you come on too strong, he will lose interest.

Flirting doesn't mean taking the conversation to sex. It's actually a lot easier to flirt with us guys than you think.

Here are my 3 tips for subtle flirting with a boy on chat:

  1. Hello You or Hello Mister are great ways to show you're into a guy. I can't tell you why, but I love it when a girl sends this in a text. I've also noticed, only when a girl is into me does she say "hi" in this way. It's a subtle form of flirting, but it works girls!
  2. If you're getting dressed to go out, send him a pic of your outfit and ask him what he thinks. Girls think guys only want to see them half-naked. While this might be true to some extent, we also love a lady who is dressed to kill.
  3. Compliment him. If he posts a new pic on social media, he updates his profile pic or even sends you a picture of himself, let him know you like it. Using his full name in the compliment is also a big turn on. For example "like the new profile pic Matt, looking good ;)"

#6 Should You Sext Him?

With the rise of dating apps, sexting has become somewhat of a norm. But should you sext a guy you are trying to impress on chat?

This is entirely up to you, but I would say you should refrain from doing this in the beginning. If it's not your thing, don't do it at all.

Sexting should be reserved for couples or guys you have built some sort of relationship with. Remember, everything you put online or in chat has the potential to resurface later.

You have to know you can trust someone before sending naughty texts or messages.

If a guy is pressuring you early on to talk dirty or asking for sexy pics, trust me; this isn't the guy you want to hook up with. He will lose interest quickly, even if you do engage, and likely has zero intention of wanting to meet up with you.


The most important rule when trying to impress someone is rule number 2, Be Yourself 😊.

Maintaining a false facade can be exhausting. And, when he discovers you were dishonest, he'll likely ghost you forever.

Make an effort to keep the conversation going. The old rule of ignoring guys to make them chase you doesn't work. Dating apps allow us to match with someone all the time. If you ignore a guy, he'll just move on to the next match who shows more interest.

The most important thing is to have fun. If you show you're having fun texting with a guy, you'll keep him interested.