How to start conversations on a dating site with women

How To Start Conversations On A Dating Site With 300% Higher Response Rates

By Joshua Pompey



You know what I hate just about more than anything?  Wasting time.  There’s so many better things I could be doing.


Chasing my lifetime goal of eating the world’s biggest sandwich.  Contemplating why ice coffee cost more than regular.  Trying to figure out why cat’s are terrified of cucumbers.


Okay maybe those are bad examples of time productive activities.  But if you haven’t seen youtube videos of cat’s terrified by cucumbers, I strongly urge you to click here now!


Back from the cat videos?  No need to thank me but you are welcome!  Now let’s get serious and talk about why you are really here.


If you feel like you’ve been wasting your time writing emails and don’t know how to start conversations on a dating site with women online, don’t worry because you are in great hands.


My average clients response rates go up well over 300% after working with me and today I am going to outline step by step how to we about starting conversations on dating sites with 15 of my most important tips.

How to start conversations on a dating site

1. Keep your message reasonably short.

We are in an age of almost non-existent attention spans.  Always keep this in mind when you start conversations with women online.


Your messages should be interesting, but relatively short and to the point.  An ideal length for the 1st email is 3 to 4 sentences at most.  On follow up emails you can write incrementally more.

2.  The structure of your email is extremely important

See how this article is written?  None of these paragraphs take up more than 2 to 3 lines.  Data shows that people are more likely to read things that are divided into very small paragraphs.


When women open emails that look long and bulky paragraphs, they tend to just skip to the next message. Always make your email easy on the eyes.

3.  Write with confidence

Suppose you were to approach a woman at a bar with your head down and said to her, “So umm, I really think you are beautiful. If you are interested, I really would love to talk to you.”


Would a beautiful woman who is in high demand want to engage with you?  No chance.  The body language and wording shows a complete lack of confidence.


Women love men who ooze confidence and appear to be in high demand so you need to write in a manner that reflects this.  Avoid phrases such as, “I hope to hear from you,” or “if you are interested,” and use language that reveals you are confident.

4.  Open with something humorous

Far and away the best way to receive a response is to just be funny.  Making a woman laugh online will allow you to stand out from the competition, appear more interesting, and make women think you will be a fun first date.


In addition, opening with humor shows that you were willing to put in enough effort to be interesting and make women smile, which will not go un-noticed.

5.  Do not try to flatter your way into a response.

Writing an email about how beautiful a woman is or how perfect she seems may feel like you are being sweet, but this is a highly uneffective approach.


Men and women alike love the thrill of the chase on some level and women are more attracted to men who seem to be in high demand with other women.  Bending over backwards to compliment a stranger you don’t actually know will only lower your value, and consequently, your ability to attract.

6.  Find the biggest commonality you can to focus on

Another great approach to starting a conversation on a dating site is to focus on things you both have in common.  People are usually drawn to other people they have a lot in common with so try to make that the focus of your question.


The more unique the commonality you can find, the better.  For example, most people love live music. However, if you happen to notice that you both love the same band that most people don’t know about, that is a much more interesting commonality to build off of.


The truth is, Most peoples favorite topic is themselves. If you spot something in your object of affections profile that he is truly passionate about, make that the focus of your email.  Dog’s always work great if you find a dog lover!

8.  Never Just Say Hey, HI, Or What’s UP

how are you text

This is the easiest way to wind up in the delete bin.  Simply saying hey, hi, or what’s up is the equivalent of holding up a sign that says, ““I have absolutely nothing interesting to say,” or “I gave up trying to be interesting because I’m having no success online.”


Creativity and effort will go a long way.

9.  Don’t Be Afraid To Be Completely Random

In an episode of the show Master of None (A Netflix Original), comedian Aziz Ansari tackled online dating as the subject matter.  His first line on Tinder was, “Going to Whole Foods, need anything?”   It’s silly and harmless, but something like this can be highly effective.


Would I recommend using this?  Definitely not since it was already on television.  And it also will appear as if you spammed this out to 100 women.  If you are going to use a line, add something to your email that proves you read her profile.  But the point is, being random can be a good thing sometimes.

10. End Every Email With A Call To Action

Your email should always end with a direct question that makes it easy for the other person to respond. When you don’t ask a question, you are putting all the heavy lifting on the other person to think of what to say back.


This drastically reduces the likelihood of a response.  The easier you make if for a woman to write you back, the more likely she will.

11.  Your Call to action cannot require too much thinking

You want your question to make the other person excited to respond.  But you don’t want your question to require too much thinking.


For example, starting a conversation online by asking a woman what the craziest thing she has ever done in her life might sound fun in theory, but in reality, it requires her to think really hard for a good answer.  And if she can’t think of something?  She’ll probably just move on.


A better way to ask that question would be, “Alright Ms. Adrenaline Junkie, I definitely like your sense of adventure.  Fun question, if you could knock any adventure off your bucket list right now, what would it be and why?”

12.  The call to action should come at the end of your email

Think about the conversations you have in real life.  You don’t start with a question and then make a bunch of statements.  You ask your question, the person responds, and the exchange goes on from there.


Online dating should be no different.  Always place your question at the end of the email so that it is easiest to spot and easiest to reply to.

13.  Never ask more than 1 question per email

Remember, people have limited attention spans these days. More than one question per email will make it feel like you are giving a homework assignment to the other person. Not to mention, people are very busy these days.

14.  Don’t use wasteful words

Once again, time is of the essence in the modern era.  Many women get dozens of emails a week, sometimes even per day.  Make sure your email is interesting, but choose your words wisely and cut out any unnecessary filler.


Each word should have a purpose.  It might be to make her laugh, connect with you, or spark an attraction.  But if there’s no purpose to any of the words and they don’t contribute towards building an emotional connection, then they don’t belong in the email.

15.  Ditch the slang and abbreviations

If u talk lke dis women will not luv it.  I get it.  We are all pretty busy these days.  And most of us use abbreviations and shortcuts when we text our friends.


But it’s important to keep in mind that these aren’t our friends.  These are strangers who have no idea what our intelligence level is nor do they know if we have drive and ambition in life.


You don’t have to be insanely proper with your writing but keep it grammatically correct and avoid the shortcuts in order to unintentionally send the signal that you are lazy.

Want the best material in the world for starting conversations on dating sites?

Joshua Pompey has been helping men regardless of looks, age, and background to find online dating success since 2009.  For instant access to the best material that he has been using for a decade, click here now.


Is your profile designed to attract high quality women?  Even the best emails will get deleted without a flawless profile.  Learn more how our profile writing specialists can help you by visiting this page.

Joshua Pompey Has Been Featured On: