3 Essential Tips for Online Dating Message and Email Writing

online dating message
  1. Keep it short,
  2. Help her think, and
  3. Walk a mile in her shoes.

I don't usually start off a post with the impact points right at the beginning. But I want to lay these out first -- because they're so vital to solid message writing -- and we'll get into the "whys" and the "hows" in a moment.

I was going to write about something else today -- I have a couple of big-concept posts I've been meaning to write up and get around to -- but, heck, the last post I put up was a big-concept post so I figured let's have a quick breather from that and get something a little lighter up first.

This topic came up as I got to an email from a reader. A very well-spoken and clearly an educated guy, he sent me a message detailing a situation with a girl he knew... and boy, was it detailed. I mean, it was long. Really long.

I've been all too guilty of this myself -- sending super-long messages. And what I found was that I was often disappointed -- I'd put all this time and effort into a monster of a message, and then... I'd get no response.

There are a bunch of lessons I eventually took away from those experiences that I'll share with you today. The basic gist of today's post is, basically, that this -- what we're about to talk about -- is how you write online dating messages and emails that don't get ignored... and, in fact, get you exactly what you want: responses, phone numbers, dates, and success.


Talking to Strangers is Different

I like to be thorough, and I like to cover all the points. If you've read many articles on this site, I'm sure you already realize this.

Problem is when you're talking to strangers. You know, people who don't know you from Jack -- you may be an exceptional human being, but they just don't know that yet.

So, you write out a really long, thorough, detailed message to someone, and you send it -- and she never writes back. Confused and maybe a little miffed, you write her off as obviously not realizing what an awesome guy you are. Obviously, she ain't that sharp of a gal to pass up a guy like you.

But it's not her. And it's not you, per se -- it's your message.

One of the basics of investment and the Law of Least Effort is that, the more invested someone becomes in you, the more willing they are to invest more in you.

e.g., it's like saying when you've got $10,000 invested in Stock A, and $0 invested in Stocks B, C, D, and E, you're more likely to put your next $100 into Stock A again because you know it and trust it and that's your routine. When your broker tries to hard sell Stock E at you, you're likely to just tune him out and tell him you want to invest in Stock A again, unless he presents his message exactly right.

People are like this with all of their investing strategies. They prefer the known over the unknown; they stick with what they're comfortable with.

And when you're a stranger, you're neither known nor comfortable.

Hence, the importance of solid email writing and online dating messages. Without good, solid, effective message writing, you're going to be left out in the cold while people invest in things they already know -- instead of in you.

And make no mistake, time is an investment. And mental footwork is an investment.

When it comes to message construction, these are your primary considerations:

  • The more time it takes someone to read your message, the more you're asking her to invest.

  • The more your message makes someone think and rack her brain to respond or figure out what to do next, the more you're asking her to invest.

  • And if you haven't thoroughly streamlined your message by considering how it's going to affect her, you risk forcing her to invest heavily to overcome prejudices or feelings of offense you've elicited in her by saying something clumsy.

And if you make her work hard, and she isn't already invested in you, she's almost always going to simply not do so -- she just won't be willing to put the work in.

When I got that long email from that reader, I took one look at it, then looked at all the other things I had to do (this was when I was packing up, trying to finish up a number of things on my to-do list, and trying to get set for a 30 hour ride on the Transsiberian Railroad), and figured I'd try and get back to it later.

I didn't end up remembering to respond or having the time to skim it and write a proper response until today -- half a month later. And, try as I do to respond when I can, I probably have other long messages I've gotten that I've simply not had time to respond to when I got them and forgotten to ever go back to.

And women on the Internet aren't running their own websites, their own businesses, or trying to give back. They're just plain old looking for a guy they like. What that means for you is this:

If a girl passes over your message because it's too long, or too hard to figure out, or asks her to do too much mental footwork, she plainly and simply isn't going to circle back to it later.

She's just going to move onto the next message... and you'll never know what happened.

online dating message


Spelling Out What Makes a Message Work

We'll get into some examples in just a minute. Before we do though, let's take a quick look through the mechanics -- the nuts and bolts of how emails and online dating messages work.

First off, length. What's a good length for your first message to a stranger?

Well, it depends on the context, of course. But I'd say, keep it to two brief paragraphs maximum, with perhaps a one- or two-line goodwill statement at the end.

That means that that six paragraph novella you wrote for that cute girl from Match.com probably didn't get replied to because... man, it was way too long!

She looked at that and said, "Nuh-uh."

It doesn't matter how good of a writer you are. I consider myself a fairly good writer -- I've been writing for a pretty darn long time -- but when I first plunged into online dating a number of years back and shot girls a bunch of long messages, all of which were exceptionally well-written, of course, I got back diddly squat.

They just didn't even bother to read them.

Now, that's not entirely true... I did have a few girls reply back then. But it was always much more of an intellectual discussion, and a lot less of an, "Oh boy, it's on!" kind of situation. And the interest in the discussion usually petered out after a few messages and ran its course.

And on top of that, the amount of time and effort I put into constructing those incredibly long messages simply wasn't justified by the meager returns they generated.

Good rules of thumb on message length:

  • The less well she knows you (e.g., a message to a girl you liked the profile of from an online dating website, versus an email to a girl you met yesterday and spoke with for a few minutes), the shorter your message ought to be.

  • On follow-up messages, pretty much never go excessively beyond the length of her last message to you... and generally, write just a little bit less.

  • Visual appearance is key -- you can feel like you're not saying much, but it takes up four paragraphs. Cut it down. There are ways to say more in two short paragraphs than in seven long ones.

  • You don't have to reply to everything. If you're thorough, like I am, there's always the inclination to refer to every single point she raises to ensure she feels understood, but this can lead to excessive length. Choose the most substantial points, and respond to those.

The second thing you need to pay attention to is helping her think. That means that questions like, "Tell me about yourself," are way too vague and are going to lead to women briefly scouring their brains for an answer, drawing a blank, and deciding to "come back to your message later"... and then later never arrives.

Leaving out a call to action is equally bad. You'll notice at the bottom of this post there's a call for you to jump on my newsletter. That's on all my latest posts, many of the most popular ones, and I'm gradually going back and adding it to all earlier posts.

Why? Because if I don't make it clear what a reader ought to do and make it easy to do it... readers are unlikely to do it by themselves. It's too much mental footwork, and people -- everybody, just about -- want you to make things easy on them.

If I told you, "Hey jump on my newsletter... you've just got to head to this other page and fill out ten fields of information," you're going to think, "Nah, that's too much work."

If instead I say, "Put your email in RIGHT HERE and click the button and you'll get tons of awesome insights," though, well -- you're a lot more likely to say, "Sure, why not?"

Likewise, if you write a message to a girl that's devoid of calls to action -- clear, easy calls to action -- she's not going to know what to do with that message... or if those calls are too complicated, she's going to feel unmotivated to comply... and unless she's crazy into you, she isn't going to do a thing.

Compare the following short messages:

Message 1

Lily, hey. That sounds like a wild experience you had with the apartment flood. I'm glad MY apartment is high enough in my building I don't have to worry about that!

No big plans for the weekend; just hitting the beach on Sunday maybe.


Message 2

Lily, hey. That sounds like a wild experience you had with the apartment flood. I'm glad MY apartment is high enough in my building I don't have to worry about that!

No big plans for the weekend; just hitting the beach on Sunday maybe. What say we head there together? I'll bring some food and we can do a picnic.


Which message is more likely to get a response?

Which message is more likely to get a useful response, that moves the interaction forward?

That's right; Message 2 is vastly more likely both to get a response, and to get a useful response. That's because it includes a clear call to action and it makes it a LOT easier for Lily to decide how to respond.

The response Ted guides her to responding with is, "Sure, the beach sounds fun! What time do you want to meet?" He makes it very easy for her to know what to do next; thus, he also makes it a lot more likely she responds.

In Message 1 there's no clear way for Lily to easily respond back; she'll write a response if she's chasing very hard, but even then it isn't going to be the best kind of response; it'll most likely just awkwardly try to force rapport where no doors had been left open for it (by Ted).

You need to make it easy for women and help them think to avoid ending up with message abandonment issues.

Do these things:

  • Ask simple questions
  • Share simple stories that don't require much analysis
  • Add clear calls to action that are easy to say "yes" to

Those three things will improve your reply rates to the messages you send so much you'll want to shake my hand.

Finally, walk a mile in her shoes. This should go without saying, but you'd be surprised how often messages get written without a guy stopping and considering how a girl will receive them.

Still these days I'll be about to hit "Send" on an email or a message I'm sending to someone, and I'll stop, read through the message as someone else, and realize, "Whoa, this is still way too long, I need to cut out some paragraphs," or, "Oh man, I'm just talking about myself here... this sounds totally self-absorbed and not like I have any consideration for them at all," and I'll go back and make edits.

Always take the time to imagine how you'd receive a message like the one you're sending if you received it from a stranger. If you'd feel a little annoyed at the length or the tone or you wouldn't know how to respond to it, you have some edits to make.


What a Good Online Dating Message Looks Like

online dating messageI'll note that while I don't talk about online dating a whole lot on here, I used to do it quite a bit as a supplement to meeting women in the real world. It's useful too for getting good at learning how to write to women and finding out what's effective and what isn't.

You'll want to keep in mind our three rules from the beginning of this post:

1. Keep it short,
2. Help her think, and
3. Walk a mile in her shoes.

That means long, detailed first messages are out.

I know, it's tempting when you read a great profile or find a girl you're REALLY excited about to write her a novel telling her everything about yourself and relating it back to her -- such a message can even feel like a masterpiece as you put it together -- but take it from me (having written many such masterpieces in the past) -- yeah, those don't work.

No matter how beautifully constructed such messages may be, no matter how much of a perfect match the two of you really are, a girl's going to see a monster message like that, and instantly click the "back" button.

So it's got to be short.

You've also got to help her think and make it intellectually undemanding. Even if she's a Ph.D., she doesn't want to come home from a tough day at the office, open up her inbox, and find a message challenging her to share 3 unique things about herself or define her favorite 19th century poet. She's going to hit "back" on that one too.

So it's got to be easy and it's got to help her think.

And you've got to be thinking about what mindset she's going to be in while reading this. She's probably reading a ton of messages from men -- it's an online dating website, after all -- and she's hearing a lot of the same thing -- a lot of:

You're so beautiful. I think we should go out.

and a lot of:

Hi Casey, my name's Charlie. You seem nice. What do you do for fun?

and a lot of:

If you like this picture of my dong, there's a LOT more where that came from. 555-555-5555. Call me and let's set it up for a hot, sweaty night of ass-smacking ridiculousness.

so you know she's getting tired of that. So you also know you've got to be different, intriguing, and light -- she should enjoy getting a message from you.

So a good online dating first message ends up sounding like this:


Bienvenido & Your Art


Hey Casey. Welcome to town; hope the locals haven't been too rough on you. It's only bad until you're initiated ;)

So, found it cool that you're an artist as well. Too forward of me to ask what kind of art...? Going to rule out stonecutter, since it doesn't look like you have the forearms for it..

Anyway, cool to meet you.


The base content -- welcoming her to town because she's new; asking her what kind of art she does -- that's going to be pretty standard; lots of guys will have asked her that. But if you throw in some unique perspectives -- joking that she doesn't look like she'd be a stonecutter, telling her the town's only bad until she gets initiated -- you're a lot more likely to capture her interest and get a reply.

Also note that this message is short; it helps her think by giving her an easy way to respond to the next message ("haha"ing about the stonecutter comment / the "getting initiated" comment and responding to the question about what kind of artist she is); and by providing a lot of unique language and phrasing, it keeps things fresh for her and sees it from her perspective, providing a message she'll actually want to read.

Here's another potential opening salvo:


Whatever you do, make sure you don't open this message...


Stella, hi. Saw that you classify yourself as a "free spirit," which I'm guessing means you do things like spend afternoons in the sun and... trespass on personal property, maybe (if you're a free spirit like I'm a free spirit, anyway :D ).

Chapel Hill caught my eye -- that's my second favorite part of town. How long've you been there? Maybe I've bumped into you there before (or trespassed on your personal property...).


All the same points as the last message, except pay special note to the attainability statement in the first paragraph ("if you're a free spirit like I'm a free spirit, anyway :D"). If you take that statement away, the first paragraph sounds a little rude / accusatory. You might not notice that unless you take a moment to walk a mile in her shoes -- but as soon as you do, and you add that statement in there, now suddenly you've transformed an accusation into a neat little "us vs. the world" sort of set up.

There's also a "theme" in this message, of trespassing on personal property. It's a little funny the first time, and it's unexpected and a little funny the second time. It ties the message together and makes it stronger, and you've quite possibly created an inside joke all on your own (she's likely to write back joking about trespassing on personal property next time if she has a decent sense of humor).

Now all you do is trade a few short messages focused on getting to know her, and by the second or third day the two of you correspond, you ask for her contact info / set up a date.

I specify the day instead of the message here because there's a chance you trade 10 short, jokey messages back and forth in a day, or one message a day, and it isn't the message count that matters so much as how comfortable she's gotten with you.

If you wait until day four or later to try to set things up, chances are that attraction's expired to the point that it's too far gone and she'll just be evasive or say "no."


What a Good Email Looks Like

Emails tend to look similar to online dating messages, except a little bit meatier and less focused with capturing short attention spans. If you have a girl's email, chances are you've met in person and exchanged some conversation already at this point.

A good first email to a girl looks like this:

Gina, hi~

Great meeting you yesterday. Was awesome to both find the book I was looking for and make a cool new friend at the same time. Books and a bonus!

How'd that test you had today end up going? Hopefully you aced the hell out of it and were the first one done, and all the other students glared at you in envy as you glided out the door to take the rest of the day off.

Thinking we ought to grab a bite or a drink sometime soon. Let me know if a weeknight or the weekend is better for you, and we'll set the unstoppable gears of planning our liaison in motion.

Talk to you soon~


Note that, again, we keep it relatively short, though not so short as an online dating message since you're already familiar with this girl at this point and she's familiar with you.

You help her think -- telling her that you like her, without being overbearing about it; asking her how her test went, and then painting a rosy picture for her so she feels good even if it sucked; and including a call to action at the end.

And finally, we think about it from her perspective -- keeping things both interesting, and upbeat. If she's had a hard day of test taking, offering her an upbeat alternative gives her the chance to escape into your message -- and a date painted as an escape sounds quite inviting too.


Learning to Write Killer Messages Every Time

online dating messageMessage writing can feel daunting at first, but understand that it's both a skill and an art -- like well nigh everything else. It's something you improve at with time, and it's something that if you remember to apply the fundamental rules of success to it, you'll maximize your chances of doing okay at from the outset.

Once again, those fundamental message-writing rules are:

  1. Keep it short,
  2. Help her think, and
  3. Walk a mile in her shoes.

If you're a message writing novice, I'd suggest setting up some free accounts on online dating sites like PlentyOfFish.com and OKCupid.com and playing around with headline writing (headlines are what get women to read your messages) and message body writing (the body, in conjunction with an engaging or intriguing headline, is what gets you replies).

The lessons you take away from online dating message writing can be readily applied to email writing, texting, even voicemails, phone conversations, and face-to-face interactions. You get pretty rapid feedback -- if women aren't responding, or if they're taking a long time to write back, or if they're writing back but their responses are tepid, you know you've got some revision ahead of you.

And whenever you aren't getting the results you want, take it back to the basics, and ask yourself if you're keeping it short (long messages are scary), if you're helping her think (is it easy for her to understand you and respond to you?), and if you're walking a mile in her shoes (is she going to want to read your message, is she going to enjoy it and feel good, and is she going to want to write back and have further interaction with you?).

Happy messaging, and see you on here again.


Chase AmanteAbout the Author: Chase Amante

Chase woke up one day in 2004 tired of being alone. So, he set to work and read every book he could find, studied every teacher he could meet, and talked to every girl he could talk to to figure out dating. After four years, scads of lays, and many great girlfriends (plus plenty of failures along the way), he launched this website. He will teach you everything he knows about girls in one single program in his Mastery Package.


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Kash's picture

Does this article apply to social websites such as Facebook, twitter, etc?

BFJ's picture

Just found this article from last year and as much as I like and and plan to give the ideas some play time my experience has been pretty different. I think most of it is your pictures and a little luck but I'll report back if I'm proved wrong after trying your ideas. All the women that I picked-up on line were caught with humor, nothing else has worked. An Irish woman included that she missed men with an Irish accent - I sent a quick message that said "I can totally fake an Irish accent you should hear it!" - two year relationship, another said she was looking for men over 45. 43 at the time I sent her a message that just said, I'll be 45 in a couple of years, you should wait for me" - had a date the next night. Go figure.

jason gray's picture

So I met a girl online, we exchanged a few great emails over the day, she would reply right within an hour or so and had a good connection going.
I asked her what she did for work and she responded with something about being a numbers person and asked what I do..
charming and witty as I am I took this opportunity to say, if your a number girl how about you give me your's and i can tell you about my construction business over the phone
she responded with something along the lines of awesome as you are not comfortable yet maybe later..after we got get to know one another.

i then emiled her a message with 3 things:
1 a cleverly worded joke about how i like that she didn't fall me trying to get her number there, knowing my humor and the pervious messages thats not the problem i don't think
2 told her about my job
3 changed the subject to something other then my job. so top 5 tv show's.Problem is I rushed and forgot to ask her to tell me her's and she never responded.

what should i do, wait it out a more couple days or email her bringing up something else or lastly move on. don't really want to cus of all the girl i've met so far she the only interesting one

Anonymous's picture

She's already over you. Your first mistake was backing down. If she says no, you must reciprocate, not explain away and sacrifice your integrity in the process. It only makes her lose respect for you, as weird as it sounds since you were answering her questions and complying to her guidelines. It's more the process than the actual subject of the conversation. I believe it's been compared to dancing. Somebody has to lead, and if she was the type to do so, she would have started to after you offered.

che's picture

hi chase,

discovered your site a month or two ago, wish i'd discovered it 20 years ago! or at least 5 years ago when i first heard about 'pickup' ...

are you still based in beijing? if yes, then you may well be familiar with a smartphone app, Wechat, which can be used to search for and chat with other users. i guess it's like a combination of MSN messenger and sms text messaging.

this could be a valuable tool for meeting girls. i've had varying results with my experiments but i'm having a hard time. haven't managed to meet someone face to face yet.

i have no problem with text messages- keep them, short, don't try to build rapport and focus on arranging a meet, but that's with people you already met face-to-face, or dated already ...
how can we go about creating attraction and comfort with a girl using this new medium?

perhaps you could write a post about this? thanks ...

couple more things - what's the situation with coaching? i'm in shanghai and may be interested.
if you're ever in shanghai i'll buy you a beer,


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