how to ask a woman out online

How to Ask A Woman Out Online:  A Step by Step Guide To Success

By Joshua Pompey

how to ask a woman out online

Congratulations!  You’ve created a great profile, have put together the right photos, and have an incredible woman exchanging emails with you.   The only question is, how should you approach asking her out?


When and how you ask a woman out could be the difference between a first date happening and a first date never coming to fruition.  In the online world, we are always just one wrong move away from losing a woman to the next guy in line.


So let’s make sure we understand the right way to ask a women out online


Step 1:  Do not ask a woman out online until you’ve seen multiple indicators of interest


woman texting on the couch


Before you ask a woman for her phone number, it’s critical to gage her interest level.


Sometimes this happens within the first two or three email exchanges (usually if her messages are on the longer side) and sometimes it will require five or more emails (the shorter the responses, the more messages it takes).


Below are the most common indicators of interest:


  • She is responding to your messages rapidly
  • Her emails are lengthy
  • The emails have some substance to them
  • She has been responding for multiple days or several times per day
  • She is asking you a lot of questions
  • Some questions are personal and indicate interest in a meaningful relationship
  • Her emails are filled with exclamation points and emojis
  • She inquires about your plans for the upcoming weekend (or week)


If a woman falls into multiple categories above, you are in the clear to ask her out.   With that said, go with your gut!  If it feels like she’s ready, pull the trigger on asking for a phone number.


The idea is to never spend more time online than you have to.  The sooner you isolate a woman to a first date, the better off you will be.  If you wait too long, you run a huge risk of a woman flaking on you.


Step 2:  The correct way to ask a beautiful woman out


no deep thinking


Let’s start with the wrong way to ask a woman out.


“I was wondering if you’d like to exchange numbers or go out sometime?”


The question above seems innocent enough, and truth be told, there’s nothing wrong with it.  But we could do so much better than this.


The phrasing of the language puts all the control and power in her hands.  It communicates that you are the one chasing and that she is the prize.  In this sentence you are “wondering” and seeking her approval for a first date.


What we want to do is flip the script.  Confident men don’t wonder if a woman would like to go out with them.  They KNOW a woman will want to go out them.


A better way to ask a woman out online would be:


“…anyway, you seem like the type of person I usually get along with.   We should meet up and see if we have any chemistry in person.  What’s your phone number?  I’ll shoot you a text sometime soon and we’ll figure something out.”


See the difference?  We are no longer chasing, we are taking charge of the situation.  She’s not being asked IF she wants to meet.  It’s already assumed that you ARE meeting.  It’s simply a matter of when and where.


This is a much more confident and effective way to make plans with a woman.  As an added bonus, you are keeping the chase strong by stating that you want to, “see if we have any chemistry in person.”


This phrasing keeps things casual and communicates that you aren’t chasing her.  You’re giving her the opportunity to see what evolves.  This is a stark contrast from the majority of men who are bending over backwards to seek her approval for a first date.


Step 3:  Setting up the date


setting up a date


Sweet… You have a phone number!  What’s the next move?


Set up the date as soon as possible.  Whether you arrange your date over the phone or via text (text is now the norm), always reach out sooner rather than later.   There is a lot of competition online and we want to keep the connection strong before other men try to cut in on our woman.


Women don’t want to endlessly text a man before arranging a date, so start out with a few warm up texts, then proceed straight into asking her out.


When you ask a woman out online, you want to let her reveal her schedule first.  A perfect way would be as follows…


“We should meet up… What’s your schedule looking like this week?”


Allow her to provide the intel for when she is free, then choose a day to ask her out.


asking a woman out online is easy


Why do we want to take this approach?


If you ask for a specific day, i.e., “Are you free Thursday?” and she says no, then you have to ask if she’s free Friday.  What if she says no again?  Then you have to ask if she’s free a third time on a new day?


This makes it look like you have no life and are willing to revolve your entire schedule around when she’s free, which is an instant turn off and lowers your value.  Always let her provide the intel first.


Writing, “We should meet up… What’s your schedule looking like this week?” will always provide you with the info you need prior to asking her out.


Once you have a few days to choose from (suppose she said Wed., Thurs., and Mon.), you might want to pretend you are busy Wed. and Monday just to make it seem like are in even more demand.  This will raise your value, as men who have active social lives are inherently more attractive.


“Let’s meet Thursday… I was thinking we could grab drinks.  How does (insert name of bar) at 7 o’clock work for you…  Sound like a plan?”


It’s okay to give woman a choice on the type of date, but it’s more attractive when a man takes control by at least making a suggestion first.


Finally, this article is just a guide.  The context and playfulness of how you ask a woman out may vary, but you get the idea.  Use confident language, take charge, and be the type of confident man that woman want to meet!


Want more free advice?


In order to ask a woman out online, first you need to get to a point where she is interested!   Get started with your free education by learning how to put together the perfect photo gallery.  Click here to learn 21 of the best photos for guys, backed by over a decade of research.


You can also learn how to message women online like a pro with over 20 of my best emailing tips.  Click here to learn more.




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