Online Dating Messaging – How To Write Messages To Get The Date

online dating guide and tutorial - online dating messages

In the previous section we dealt with creating an effective profile, now let’s look at actual communication.  Never forget that the purpose of online dating is to remove the online part, and get to plain old dating as soon as possible.  Until you meet in person and look each other in the eye, all bets are off about anything ever actually happening. Keep this in mind as you exchange messages with someone.

Things are a bit different between a traditional site like OkCupid, and a swipe based app like Tinder, but the same text game rules apply to both.  With OKC many guys do the copy and paste intro message, where the same message is used for every girl messaged.  And only if she replies, do you actually write original thoughts back to her. This approach has advantages from a purely numbers perspective, no time is wasted, so maximum efficiency is achieved in terms of contacting women in a given time frame.  However I’m not the biggest fan, as I found the rate of replies was less than the technique I’ll describe below. But if you do wish to use it, make it fun. I copied a message that an online dating guru used which was a long, rambling and outrageous paragraph about what he would do on a first date. It wasn’t sexual, but it involved stealing a boat, robbing a bank, and I can’t remember the rest.  It matched his crazy profile, which had pictures of him partying, and a written description in the shape of a martini glass.  Perhaps I would have had better results if I had matched my profile to the message like him, but I wanted to be authentic to myself. Another drawback to writing a paragraph intro message, was that it broke one of the main rules of text game – equal levels of investment.

Instead I started writing quick, and short messages that didn’t delve too deep into her profile.  Most of the time they would relate to one of her pics.  Usually it was in the form of a compliment, followed by a question related to it.

For example if there is a pic of her with her dog:

“hey cute dog! What breed is she?”

The more targeted you can make this message, the better.  For example suppose she has a pic of herself on the beach, and it’s captioned – Miami spring break.

“Hey I love Miami! How long were you there? ”

At most I wouldn’t write more than two or three sentences. Beyond that and you are exceeding the appropriate level of investment for an opening message.  While you can follow the same idea with swipe based apps like Tinder, because you have to match with each other first, it’s not quite a cold approach anymore.  In this case it’s not a bad idea to simply use the same opener with everyone.  I’ve experimented with a few different ones, from the funny and bold – “So when should i set the date for the wedding?” to the casual and low on investment – “hey there”.  Both have worked although the initial conversation is different, eventually both conversations will have a similar back and forth banter.  If you’d like some ideas for tinder pickup line openers, check out these two sites by a friend of mine.  I’d recommend cheesy/corny/funny/fun over anything sexual.

On the next page I’ve posted some OKC and Tinder conversations, but before that I want to go over some text game rules.


Match her level of investment.  Investment can be gauged by the amount of text she writes, and the length of time taken before she writes back to you.  If she’s writing one word answers back to you, or taking hours between replies, then clearly she’s not that invested at the present moment.  In these situations take a similar amount of time writing back, and/or reply back with a message of about the same length.  If she’s like this from the get go and there’s no change, then there’s not much hope in things going anywhere.  If results vary, and she’s blowing kind of hot then cold, then it’s probably real life getting in the way, and things are salvageable.  The key is to escalate during those periods of good and quick replies, and push to make future plans, or for a phone call.


Text conversations, like real conversations should have a flow, with a combination of questions and comments.  Asking her questions makes her invest in you, which is a good thing.  However asking question after question results in you sucking all her energy and time, which will begin to turn her off, and cause her to subconsciously change her levels of investment.  It’s really a skill that comes with practice.  In general if you are a good conversationalist in person, then you can be a good one in texting. Both are skills that can be learned or improved upon.


Reward her investment.  If she replies with a paragraph, or is asking you questions, if you consistently write one word answers, or take hours/days to reply when she’s getting back to you in minutes, you are in essence punishing her for liking you. This is not good, and will cause her to develop negative feelings for you, and she’ll look for happiness elsewhere.


In text game, as on a date, it is generally the man’s job to escalate, and she is waiting for you to do so.  Hesitating too long to do this will cause the conversation to run dry, and will sub-communicate a lack of confidence and indecisiveness on your part.  She will lose interest.  Escalation in online game, as mentioned at the end of #1 is making your intent to meet up known, and/or pushing for a phone call.  Talking on the phone is a go to move of mine with online dating.  It separates you from the other guys that are messaging her on this app.  It takes it to the next level, so you can have a real conversation, communicate better, and hear each other’s voices, finally creating a level of intimacy.


This is really for the phone call mentioned in the last tip.  A proper intro phone call should last at least 20 min, ideally 45 min to an hour.  If you can’t talk for that long, then I’d recommend another phone conversation before actually meeting up.  But test the temperature, if she just wants to meet up then go for it.  The conversation should be light hearted banter, and just getting to know each other.  It’s better to avoid more emotional topics, and save them for a face to face.  After you’ve talked for at least 20 min, bring up meeting for a date.  She’ll be down for it.  Settle on a day.  Be flexible and aware that this can change due to your respective schedules.  For first time dates I’ve learned to keep things simple, and I’ll usually just suggest coffee or a drink, and figure out logistics.  Ideally you want to meet up within a 20 min drive or walk of either your house or hers.

To give you a clearer idea of what I’m talking about, the next page has an okCupid sample conversation with my commentary; or if you prefer swipe based apps, the page following that has a sample Tinder conversation with commentary.  If you think you’re good with messaging then skip ahead to my what to do on a date page.


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