Start with a challenge

how to chat up a girl online

How to chat up a girl online Part with a challenge. 

Starting a conversation online with a total stranger is not always an easy thing to do. Very often when you’re trying to chat up a girl online you have very little to go on beyond a picture or two from their profile. You don’t want to start asking them what they do and where they come from like you’re at some networking event, yet finding something original to say is hard.  

Open with a challenge 

Dating expert Daniel Urban* specializes in coaching men to chat up girls online and successful dating thereafter. Having analysed thousands of instant message conversations he reached the conclusion that challenge was the essential ingredient in successful approaches to women online. I'm a fan of bold statements and bold suggestions.I don’t want to offend anyone, but many women like this approach and are happy to play the game and be bold in return.This can make early conversations much more fun and brings a totally relaxed atmosphere to flirty conversation.It is a game! 

The challenge is to keep it at a playful level without becoming insulting. You have to quickly ‘calibrate’ how open the other person is to your cheekiness, approach them in a fun way test out their boundaries! 

Some practical examples of how you could chat up a girl online 

So what does chatting up a girl this way look like in practise? To a large extent it depends on the platform you are using and the amount of information you have to go on. In many instances you are unlikely to have more than a picture as a basis for your first comment, so you need to find something in that. Of course, if you’re commenting on a girl’s picture a compliment is almost obligatory. But then everyone will do this. To stand out you need Compliment + Challenge Statement. (Note the challenge statement should always take the form of a question that demands an answer/response) 

For example: “Hi there. I like your profile picture. What are those strange clothes you are wearing?” 

The tone of this opener would change depending on the platform. On a dating site like Tinder which is by its nature very flirtatious and where you may only have a limited opportunity to make an impact this line would be less respectful in tone: “Hey sexy. What’s with the funny robes?” 

On a site that is a little slower paced in its conventions, such as Match or Oasis Dating, you would perhaps approach the subject more conventionally. “Hi there. I love your profile picture. That’s a really unusual outfit, where does it come from?” 

It almost goes without saying that in all these examples, the message must demonstrate some reaction to the profile. This shows the girl you are chatting up that you are interested in her in particular and not just a message you are copy pasting to every girl in your match list.  

The response and how to read it 

Once you have started with a challenge it should be simple to keep the conversation going with anyone who responds, even if you have to resort to an apology. And the type of response you get is likely to tell you quite a lot about the girl you are chatting up: How assertive she is; how confident she is; how easy she it to offend.  

Ideally you want a girl who shares the same values and outlook as you. So the question is: How would you respond? If the answer is that you would find it funny or intriguing then maybe you are looking for a girl who responds in this way. 

Saying this, if you do cause offence with a challenging statement don’t dismiss the person immediately. Rather, you should apologise and feel your way back to a flirty form of conversation, towards the next challenge statement. In other words, give them a second chance. 

*Daniel Urban is a German based dating coach, you can read more about him on our german sister site here  

Image courtesy of africa and Serge Bertasius /