How To Send Messages | Online Dating Help | Part Three

In this blog post, I will explain why the first message that you send a girl on any dating is so important. I will go through a few basic ideas and why certain initial messages seem to gain traction as others fail miserably.

Before I begin, be sure to check out the other parts in this series which deal with how to create the ultimate online pictures for your dating profile, why certain images work, how to create the perfect written profile and what balance of values and humour serve to generate the most positive responses.


So for many guys, we have painstakingly assembled our online profile! Having gone through our entire photo library with a fine comb, scrutinised and agonised over which pictures to pull off social media and, if you’re bright enough to have followed part 1 of this series, you may even have put the time and effort in by following our guidelines and have basically injected your whole profile with steroids and are now feeling pretty sexy and optimistic with your new images!

If you have read part 2 of the series you may have now have created a written profile which is a linguistic monster oozing cool, sophistication, depth and humour whilst saying I’m not arrogant and approachable!

If you haven’t taken these steps then we strongly recommend you do!

However, if you have either followed our earlier steps or are sure your profile is strong enough to get the initial matches then today’s blog could be the icing on your online dating cake.

So your getting matches online! Everyone is different so the quality and consistency are going to be different for each individual. However, one thing rings true, with a bit of effort we are generating attention! Amazing! The online world isn’t looking so daunting. Finally, the constantly whirring conveyor belt of desirable women which seems to be just out of your reach is slowing down. Can we finally be on the verge of actually obtaining dates with some of these beauties? The online world has been dangling desirable dates so cruelly in front of us like a carrot on a string provoking us to spend money and countless hours online for too long now!

So you are getting matches and then …. Damn! It hits and you realise you have no idea what the best way to send messages is. Here are some of the most common questions I get asked as a dating coach:

How do I begin this conversation?

Should I start with a compliment?

Should I just say ‘hello’ or  ‘hey’?

Should I find some similarity or comparison in her information?

These are common queries and most guys simply think what the hell we matched so I guess a simple …

“Hey Sara how are you ?”

Or

“Hey Sara amazing pics! Where are you from ?”

Or

“Hey Sara you have beautiful eyes?”

Or

“Hey Sara how was your day/weekend?”

You send your opening message full of hope and dreams of you and this beauty running hand in hand on the beach tumbling under the covers in deep throws of passion…. and…. andddddd…. nothing, nada, nilch, zero reply. That inbox is empty, despite all your efforts to create a good profile and the fact that you matched shows she must on some basic level find you attractive, she isn’t replying.

So let’s discuss why this may be the case and how you can up your chances of success through cunning and witty initial messages!

First of all, let’s be clear, the above example of initial messages are commonly used and likely to fail. Women who are desirable online dates are absolutely bombarded with messages from hopeful guys. Not even desirable women if I’m honest,  any woman with a pulse literally gets tons of messages every week.

The first step to ween her way through all these profiles is an initial physical attraction. Ok, we covered that by crafting strong images and got the match.

Then she will receive your first message. If you look like Brad Pitt then your first message probably will be less important as you have already set yourself aside from the masses of hopefuls and a mere “hello” will probably work. However, even in the cases of guys who have heavy hitting online profiles the women who they are matching with are also dealing with a hundred other guys who have heavy hitting profiles. So, for anyone from the average guy to the hunk, this first message is the game changer.

So she receives your first message! So why oh why did she not respond? I know the pain, it’s incredibly frustrating and demoralising.

The truth is that she is just not particularly bothered. She has hundreds of matches and you aren’t bad looking but you’re not the best one and barely worth her time and effort. So…. she stays silent or at best answers with a few words and then goes silent.

Remember she is a woman and doesn’t think like us guys! Whereas guys match with any reasonably attractive girl and then basically date anyone they find in the least bit sexually attractive. We are totally motivated by sex and physical attraction.

Women online will match with anyone they find attractive and sexy yes but they also match guys who they find interesting, different, funny or quirky.

In many cases, the pics and written profile combine to seal a match and get you the attention you need to at least make you a prospect. However, in truth, you are still an outside shot at the title and without careful treatment of the first message unlikely to become a contender!

So, quite simply all the mundane first messages I covered above just don’t cut the mustard. Let’s cover some ideas on how to send great first messages. Fellas if these bad boys don’t work then nothing will and you can move on assured that you fought the good fight and that’s all anyone can do!

So firstly let’s distinguish between the two common profile types

Profile 1 – the detailed profile, the kind of profile which shows more investment thus warrants a return of investment from you. Likely to be on paid sites.

As we can see this profile is bursting with information. This girl wants to transmit a real sense of character. These descriptive profiles are often riddled with humour as well. So how do we sift through all this info and create that first message. The first thing is to decipher what is her core info. By her core info we mean her personality traits, pastimes or any other elements of her life she has seen as important or cool enough to mention. We must separate this info from the other parts of the profile which is simply mundane.  For example in this profile spending time with family, summer holidays, cinema trips and getting drunk with mates is all mundane info. We all do all these things and it says nothing about her true sense of self. The core info, however, is quirky and fun and is an attempt by this online character to show she is a desirable social prospect and different or at least cool amongst her peers. So we must find the most extreme elements of this core info and the use it to massage her ego! By massage her ego I mean make her feel good about herself. However, we must do so without simply offering direct compliments on her looks or lifestyle. The man who says:

“Hey Sara your so beautiful you have amazing eyes?”

This guy is quite simply a fan. He has offered a compliment which she quickly absorbs and forgets, it serves to increase her ego, he is just another ‘fan’ worshipping her and has in no way appealed to her sense of self beyond her basic sexuality.

However, if you can make a human being feel good about themselves on a deeper level, about the elements of their character which make them special and cool beyond their appearance then it’s virtually impossible for them to not like you. They will, at the very least, want more of this disarming flattery which cuts to the core of our existence. Chuck in a bit of humour on top and then Bob’s your uncle!

So on returning to our detailed profile. We must choose the core traits, animate them and combine them into a long tongue in cheek description of our desired date. Thus in this profile the core info is :

– cake baking which becomes cake munching

– horse riding which becomes horse galloping

– Russian speaking

– she likes yoga so she is now super bendy

– she likes meditation so she can be labelled a hippy and spiritualist.

– she does kickboxing so for our purposes today she can kick my ass.

So …

Hey Sara great profile so it seems you are a cake munching, horse galloping Russian speaking bendy hippy spiritualist who can kick my ass and has a penchant for travel and Sushi Damn girl is there anything you don’t do ? I would totally out bake you btw!!  You don’t wanna cake off with me ..

So by combining all these random unrelated elements of her profile life and personality. We are giving her a  massive ego boost and simply saying to her:

“ Yes you are all the things you want people to think you are! You are different and eccentric you life is quirky and interesting. I find you interesting not because of your looks solely.”

The human brain loves flattery and the manner in which the compliment was delivered was funny and different show you also have a great sense of humour (the most attractive trait of all), you’re confident in yourself to make a joke and tease her showing that you don’t fear her (confidence being possibly the second most attractive trait in a man). Finally the fact that you have bothered to sum up her info and have managed to focus and combine her core traits in this witty animated manner sets you aside once more. For the simple fact you are showing true interest in her as a human being. Your not instantly eluding to her sexual prowess like most men do and have managed to instantly focus on the things which really make her herself, her true identity.

Finally, let’s go back to a piece of quirky silly info like the fact she likes baking cakes and offer a challenge to show we are not simply her fan and a push over like so many other guys and can rise to a challenge. The fact we have said cake off is also a quirky funny way of describing this imaginary cake making competition!

That is the easiest way to appeal to a profile with lots of info however many profiles are way less informative and in many cases, there is simply no written information at all. This is especially so in the case of free swipe sites like tinder. Here women have not paid for membership are thus less serious about finding a partner and are just having a look or messing about. They will date guys if it’s easy and the guy is different and sets himself aside from the crowd. It is of course however very difficult to show your value and character with zero information. Thus we must do what we can …

“Hey Sara your exquisite! If your looks match your personality I reckon I’m gonna have to kidnap you 😂

We purposely use the word exquisite instead of the more commonly used phrases such as hot or beautiful. It shows we are a good linguist and already begins establishing our difference. I have already mentioned I am not a fan of compliments in an opening message. Unless followed up with a justification tied in with her personality. Thus by saying kidnap you if your personality matches we are actually saying, yes I am aware of your obvious good looks and I like them. However it is your personality matching, ie your personality also being top fleet that will make me want to kidnap you, which is obviously a joke meaning date, spend time with marry or wherever the future may take us. A beautiful person is born beautiful they don’t need to prove it or justify themselves. They are constantly offered compliments which mean nothing to them. However having a good personality is not a given. Nobody wants to be beautiful but empty so this is a massive challenge. She must prove her personality is equal if not way better than her looks and that she has real substance. Looks are skin deep and she has been reminded of that by you who obviously values deeper things about a person. She must rise to the challenge! This all demonstrates  you are high value and have options as you are not motivated purely by sex. Furthermore, you must have a great personality too if you can issue a challenge to a such a desirable woman. You are confident enough to challenge her and of course you can top off all these great traits with a bit of humour about kidnapping her. It’s extreme and obviously not serious and provokes a silly mental image of this new seemingly nice and normal guy (all transmitted buy pics and written profile) lurking in wait about to bundle her into a van!

So gentleman those are the tried and tested most effective first messages. However I will give you a final bit of online gold with the second attempt message or the “she has gone quiet message”. So basically we have now sent our first message. Still no response  so finally we can pull out the following and hope for a response:

Heyyyy Sara it’s me again 🙈..I know you must have 1 million admirers on here which makes me 1 million and 1.. bad odds !! But forget all those other chumps I am by far the funniest..talk to me !!  I bet I can make you crack up !!

Upon sending this message we have already been making advances and our equal standing with this woman is now challenged. We are chasing and thus to some extent have always sacrificed our integrity. We want her and she knows it. Thus the best thing to do is admit just that. By saying “It’s me again” and using the 🙈 I icon this is dealt with in an open and cool manner the worst thing to do is simply to continue messaging. With zero response. There is nothing more creepy than the following chat breakdown.

Example of all hello and hey and your hot

So having admitted your keen, though the  language here has shown you are not weird or desperate but determined and persistent.

Now you must show you are different from all the other guys she is ignoring! How can we do that? By elevating our status and challenging all these other hopeful admirers you are simply showing you are confident of your ability and high status and are an alpha male amongst your peers. You can’t challenge them all to a fight or a penis measuring contest or a bank account inspection (although emphasising high value in these categories is what most men are doing constantly subconsciously throughout there lives and are what women appeal to most on a base level). We can, however, challenge them on a sense of humour. A good sense of humour is not material and showing off about your ability to be funny does not make your arrogant. Finally, we label other guys as chumps a confident and funny way to exclude every other man on the planet, we ooze value and high status in doing so. We then close with a final challenge in betting her you can make her laugh. Everyone likes to laugh as we already know and everyone likes a bet or challenge especially when it is as easy as being made to laugh. Hopefully, she is compelled to answer and will probably say something like

“Ok funny guy make me laugh !”

Then buddy you had better do just that for the next twenty or so messages until it’s time to move onto WhatsApp and you are one step closer to that dream date!!

For more information on our date coaching and online day coaching services or to get help creating the ultimate online dating photos and profile be sure to check out our services at ….

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Ollie Pearce

Ollie Pearce is a professional model and fashion stylist with over ten years’ experience as a fashion, fitness and social skills coach. If you have any questions, ideas for future blog posts or videos, or would like to work with Ollie then get in touch at ollie@olliepearce.com.