how to start conversations with guys online without looking desperate

How to Start Conversations With Guys Online WITHOUT Looking Desperate:  3 Proven Methods Backed By 10 Years of Data

By Joshua Pompey

how to start conversations with women online

How to start conversations with guys online


It’s no secret that I am a HUGE advocate of INITIATING conversations online as opposed to waiting for quality men to FIND YOU.


Why?  Just think about your own life and behavior patterns on dating sites.  As a high quality woman, you probably have a busy career, an active social life, and a wide range of interests.


By the time you finish your daily routine, you probably have very little time or energy to perform searches and initiate conversations right?  This is more than understandable.  You live a full life!


The quality guys on dating sites are in the exact same situation.   Since they also live very full lives, they also perform the least amount of searches.  More often than not, they just wait for whatever women come their way because they are so busy living their lives.   This is why it is so important to actively search and start conversations. But I get it.  Many of you fear that sending the first message will make you look desperate.


Not to worry.  Learning how to start conversations with guys online without looking desperate is easy.  It’s all about how you approach the first email.  Let’s take a look at 3 types of emails you can use to initiate.


1.  I have no idea if we’d get along but…


With this conversation starter, you need to find something in his profile that you both have in common. Preferably, it should be something that you are both really passionate about.


Let’s take a look at an example of how this opening message might look:



I have no idea if we’d get along, but I just had to message you because I’ve also seen Bruce Springsteen OVER 10 times! I was beginning to think I was alone in my obsession with him. Lol… Where was the first venue you ever saw him play at?


Framing the dialogue in this manner paints the picture that you weren’t TRYING to go out of your way to message him.  But how could you pass up on letting him know that you are also such a big fan of the same musician?  You felt like “you had to message him” about this.


The framing of the language creates the image of a woman who just happened to notice that she shares a really strong commonality, as opposed to a woman who is actively TRYING to find someone with commonalities.


In addition to not looking desperate, you are creating a subtle chase by stating,  “I have no idea if we’d get along.”  Men like a little bit of a chase as opposed to women fawning all over them.  This language lets him know that you are interested to an extent, but he can’t go ahead and cash that check just yet.  You are simply exploring the possibility of a connection.


Finally, this type of opener establishes that you both share a strong commonality.  This will help to raise interest and build the feeling that there is a potential connection in the works.


2.  Focus on the context of a picture



See the picture above?  I photoshopped that picture of myself as a gift to all you ladies out there.  Sexy, I know.  You’re welcome!


Just kidding of course!  But suppose I posted this in my profile to make women laugh and bait them into a conversation.   If you saw this picture and were interested in me, you could open up a conversation by focusing on the context of the picture.   Perhaps you write something along the lines of, “LOL that is hilarious! So on a scale of 1-10, just how well is that picture working?”


These conversation starters have a laid back feel because they are painting the image of a woman who just happened to notice a picture, not a woman who is actively pursuing a man (even though you are actively pursuing the guy!).  It’s all about having that laid back and matter of fact approach.


3. It’s too bad you’re a…




Let’s pretend you happen to be a Met’s fan and you see a picture of a man wearing a Yankee’s hat.  Maybe you were even lucky enough to come across Denzel Washington himself on a dating site, as depicted above (a woman can dream right?).  A great opening email could be:



It’s too bad you’re a Yankee fan… we really had the potential to be something special… 😛


This works on a variety of levels:


It opens the conversation with a playful flirtation and will spark a fun dialogue that is simultaneously tapping into a mutual interest.


It requires him to chase you in his response. He’s most likely going to give a playful reason why you both could still work, in spite of you being a Met’s fan.


It allows you to use a flirting technique called push pull. You are pulling him in with something nice (we had the potential to be something special), then pushing him away with a reason it wouldn’t work (he is a Yankee fan).


This type of email can be used on any topic that you have a slight difference of opinion on, but you will want to avoid serious topics (politics, religion) and stick to topics that are fun.  It is also most effective when you are focusing on something that you both are very passionate about.


Looking for some more free online dating advice?


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