How to Ask a Girl Out on the Internet

You’ve signed up on the perfect dating website with your sharp profile and flawless display picture and you have already successfully woo’d a few women with strong pickup lines. The conversations between the two of you are going great, you are pretty sure things are working out in favor of you and the women are gradually falling for you.

It’s now time to start asking them out. But this is a little different from what you have been doing so far. If you do not know how to ask a girl out on the internet properly, don’t be surprised if the girl never comes back to talk to you.

Before you can turn your online score into real-life physical action, you need to do a few things to make sure it happens in your favor. Fortunately for you, we have done quite a few experiments and learned the best practices of asking women out on the internet. So don’t be blunt and ask another girl out before reading what we have to say.

Here are some of the best tips from dating experts on how to make her say ‘yes’ to your ultimate question.

Timing Is Literally Everything

When it comes to asking a woman out online, timing is your best friend. Ask a little too early, you’ll probably creep her out, and if you wait too much, she is probably going to lose interest in you and move on.

Once you learn what the best time is to ask her out, you’ll be in the front seat driving the car. Our team has gone through hundreds and thousands of online conversations to dig out the ones that worked best for the men out there. After analyzing and collecting the data, we have been able to figure out that the best time to ask her out is after she has at least sent you two or three messages.

So basically, you should follow this routine:

  • Start by breaking the ice with a clever pickup line designed to catch her attention and make her laugh.
  • After she responds to it, message her back with a personalized question that includes some of the things that she said in her response or through her profile text
  • If you do it right, she is going to respond again. This is the ideal time to just ask her out.

But are there any exceptions to these rules? Well, yes there are!

If you realize that you are the one who is driving the conversation and she is only responding with short and cautious messages, you’ll want to keep going things on for a bit longer until you sense she is comfortable with you.

Here’s How You Can Get in Her Head

For her to say ‘yes’ to you asking her out, she needs to feel comfortable meeting you in real life. While sometimes it may take a while to get her to be comfortable with you, other times, things just seem to click.

This is due to the Rule of Connectivity, a term backed by research which states – The more we feel connected to, part of, liked by, or attracted to someone, the more persuasive they become.

In other words, some people will naturally feel comfortable with people who remind them of themselves. If you are similar to them, you are also familiar to them, and in that, they can take comfort in.

So in order to make a woman feel comfortable with you, all you need to do is mimic her style in which she communicates with you. Researchers like to call this term ‘mirrorring’ and it is actually simpler than you think.

Here’s How You Can Pull It Off

Copy her style of conversation. For example, if she opens to you with a message saying ‘Hey, ‘your name’, you must respond with a ‘hey, ‘her name’.

Copy her message length. If she is sending you only two sentence responses, you must also send two sentence response. If she replies with a few words, keep your message very short and to the point.

And if she sends you a lot of smileys, you should come back with a smiley of your own. Just try not to spam smileys. Keep them to a limit of 1-2 per message.

Identify When She Is Ready to See You in Real Life

Identifying her intent is actually very easy. The trick is to pay attention to what, how much, and in what kind of tone she is replying to your messages. If you are lucky, the girl will send you a message that will immediately help you realize that she is into you. If this happens, then you can ask her out as soon as the opportunity arises.

But if you are the kind of guy who struggles to understand how women think, don’t worry. Here are some signs to help you identify what she is thinking about you.

She starts sending you lengthy messages – If you see her message length becoming larger than yours, then this is a sign that she is pretty interested in you. It also means that she is open to you and comfortable to meet you.

She’s sending a lot of emojis – smileys, emojis, and funny characters using text is the internet way of showing that you are excited, enthusiastic and happy about something or someone. And you know exactly what it means when a girl starts to laugh at every joke you throw at her. She either really wants to please you, or she thinks you are really funny. Both are good signs for you.

She starts taking a keen interest in you – questions are always a sure sign that she is really interested in you. If she starts throwing questions after questions to you, mostly asking more stuff about you, then she is into you – no holds barred.

If she is displaying any of these signs, then it is up to you to man up and ask her out. Confidence is something women really dig about men. And asking her out is a way of showing your confidence to her.

Insecurity, on the other hand, is a deal breaker for a woman. If you send her messages that shows a sign of insecurity, she is just going to avoid you. So man up and ask her straight out. Don’t fear rejection.

Keep Things Simple

When asking her out online, never use the word ‘date’. Don’t start by saying ‘hey wanna go out on a date’? Instead, keep things simple by just saying ‘ hey let’s meet up somewhere’. There is a good reason behind it. The word ‘date’ is controversial. It immediately translates to intimate stuff. You don’t want to go that road when you are talking to someone for the first or second time. Getting her to come up by calling it a meeting is far less scary for her. But somewhere deep down, you and she both know it is a date anyway.

Also when you ask her to meet you, make sure it is in a small coffee shop or bar. If you keep things big and call her out to a restaurant, it is not only going to waste both of your time if things don’t go well, it will also waste your money. So it is naturally a good idea to have the first meeting at a very low-profile place where either of you can escape easily from.

Leave Her with a Choice

After going through hundreds of online conversations between men and women, we were able to figure out that the chances of her agreeing to your meet up increases two times when you give her a choice to decide the activity.

For example, never suggest that you should go for coffee or drinks only. Give her options like going for a snack or meeting up at the nearest park. When she knows she has a choice, she will probably respond with a positive answer.

Come up with Statements That You Know She Will Agree With

When talking to her, you must have a basic idea of what she will like and what she will disagree with. So make sure to always throw statements at her which you know she will easily agree to. Here are some examples.

The two of you already know it for a fact that if you want to know each other better, it is always a good idea to meet person to person rather than messaging. If you come up with a statement that covers this important thing, she will automatically agree and for you, that means she is willing to come out and meet you.

No matter how you do it, just don’t be direct with her.

Always Stay in the Front Driving Seat

Once she finally agrees to see you in real life, set a date and time. Do not leave it up to her to choose when and where should the meeting take place. This actually puts a lot of pressure on the woman and it also gives her a message that you can easily make yourself available to her whenever she pleases. Plus since you are the man, you should be taking control. Women like that kind of stuff.

What you must do to make things work is to suggest at least two options. These options should have separate times. For example, give her an option to meet on Saturday evening, or Sunday afternoon. This will make it easier for her to pick the time. It also shows to her that you are a busy guy and time is something very valuable to you.

Also, make sure these messages are short and to the point. Since she has already agreed to come out and see you, you want to make sure that she stays laser-focused on the meeting.

You can discuss whatever you want to later when she comes out in person. Once the date, time, and place of the meeting are set, simply end the conversation. No more jokes, no more statements, nothing else.

Finally, give her your contact details and suggest to her that she should send hers in case the plan changes in the last minute for her.

Owen Cashner


Owen Cashner considers himself a professional dater and amateur comedian. His passion for writing led him to document his experiences using online dating websites. All opinions expressed on this website are to further educate men on the landscape of dating. Use this information to your advantage and conquer the dating world.

Owen Cashner

Owen Cashner

Owen Cashner considers himself a professional dater and amateur comedian. His passion for writing led him to document his experiences using online dating websites. All opinions expressed on this website are to further educate men on the landscape of dating. Use this information to your advantage and conquer the dating world.

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