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How to Transition From Online Chat to a First Date

Back in 2007 I had my first experience of online dating. I signed up to Match, Plenty Of Fish and eHarmony. Tinder, Happn and these other fancy apps hadn’t been invented.

In fact, apps weren’t even around then!

After completing my profile I sat back and waited for the messages to come pouring in.

They didn’t. Not a single message.

I’m not the best looking guy, but I can scrub up, my profile had a couple of nice photos, highlighted my good qualities, and was free from spelling mistakes.

But still nothing.

Eventually I realised that online dating is heavily skewed towards women. Just like in real life it was up to me as the man to make the approach. And that’s how it remains to this day.

I don’t care what app or dating site you are on, as a man you need to be initiating conversations with tens of girls before you get a response. Right now I would guess my response rate to an initial message is about 5%.

Why am I telling you this? Because if you get a response to your opening message then your odds of getting a first date are excellent, especially if you do it right. I’m talking above 50%.

Most men, however, mess it up big time.

Below I’m going to outline a strategy you can use to ensure you are not one of those men, and increase the number of women you get from online dating to a first date.

I’m not going to teach you what to send in an opening message, or how to engage in the conversation.

This article is about how to go about getting the first date once you have managed to open and get a response from a women.

Your role as a man

The primary aim of chatting to a women online is to meet her in real life. And as the man, it is your job to make it happen.

  • Even if you have model good looks, she won’t ask you out.

  • Even if you have the online banter of Russell Brand on ecstasy, she won’t ask you out.

  • Even if your body is as chiselled as a body builder about to step on stage, she won’t ask you out.

  • Even if your photos show you doing cool activities such as sky diving, feeding tigers, hugging two other beautiful girls, she won’t ask you out.

  • Even if you have the most intense and deep conversation, learning everything about her life, desires and dreams, she probably won’t ask you out.

Yes it sucks. Yes it’s frustrating. But you MUST accept it 100%.

It is your role as a man to ask her out and either be rejected or win the prize.

And if you follow the process your chances of being rejected will dramatically decrease (you will still be rejected though…many times…deal with it).

The purpose of chatting online

In an ideal world you would match someone online, or simply message them saying “meet at mine at 7pm Saturday” and that’s it. But this obviously won’t work. For a women to agree to go on a date with you she must:

  1. Feel attracted. If you got a response to your initial message, she’s attracted to you. It is now your job to amplify that attraction with your attitude. Notice I didn’t say “words”. What you say isn’t that important. What you say is simply a way to convey who you are as a person, and what you attitude to life and dating is.

  2. Feel safe. A woman is at a far greater risk going on a first date than you are. Men are bigger and stronger (mostly) and could easily overpower a woman. She will therefore be naturally anxious about meeting a strange man from the Internet. It is your job over chat to help allay those fears by coming across as someone she feels COMFORTABLE and SAFE going out with. Note that I didn’t say you have to be “nice” to have this happen. We all know guys who are far too nice and this comes across as really creepy, because deep down no-one is that nice and clearly they are hiding something. You can act a little arrogant and cocky and still make a girl feel safe.

girl texting

Bottom line, try not to come across as weird or creepy by begging, pleading, being too invested or acting nice just to get her to agree to go out with you. Don’t message her saying “I’m a great guy really. I’m not a serial killer. I’m a good guy and would never hurt you”. That shit is not only needy but it’s also incredibly creepy.

Chatting online is not about:

  • finding out if she is “The One”
  • getting to know her on a deep level
  • sharing your life history

The purpose of chatting online is to make her feel attracted and safe enough to meet you in person. You can do that other stuff when you start dating her.

Move quickly

Once you feel you have messaged back and forth enough to get her feeling attracted and safe, it’s time to move fast and get something in the diary. Don’t spend any longer than you have to messaging.

Here’s why:

  • Your time is precious. As an alpha guy who has lots going on in his life and is fulfilling his life purpose, you don’t have hours to spend chatting to women online who may never meet you. You need to find out how interested they are as soon as possible. And agreeing to go on a first date with you is a big indicator of interest.

  • She’s chatting with other guys. You have her attention right now, but tomorrow a more alpha guy will come along and blow you out of the water. You must act FAST before she loses interest.

  • Mystery creates attraction. The more you chat with her, the more information you give away about yourself. And the more she knows, not only will you have less to talk about on your date, but her attraction will drop. Think of the strong, silent, lead male roles in movies. You are compelled to find out more about them, what makes them tick, why they are like that.

    If James Bond gave a speech to the women he meets about how he is an orphan and where he grew up and how he feels about what he is doing, those women would not sleep with him. Be a challenge. Be mysterious. Give women the present of trying to figure you out and unlock your secrets. They love it!

    The longer you chat, the more chances you have of screwing it up. It is unlikely that your “witty banter” will increase her attraction over time. In fact, you are more likely to say something that destroys her attraction and you lose her.

  • Weed out the time wasters. Some women do online dating for an ego boost. They have no intention of ever meeting you in person. Don’t waste days talking to these girls. I’d rather know within an hour.

  • Good online, shit in person (GOSIP) Because people online are different to how they are offline. You might have amazing chemistry and conversation with a girl online, only to then meet in person and discover: her photos are old and you no longer find her physically attractive / she doesn’t find you physically attractive (happens a lot!); you don’t like her accent/she doesn’t like yours; her real-life chat sucks (online you have more time to compose a witty response, or even get help from your friends); or something else about her personality that you only notice in person grates on you.

How quick are we talking?

As a rule, aim to arrange a date within 24 hours of her initial response to your first message, ideally within the first session of back and forth messaging. Clearly if she takes 22 hours to respond this might be unrealistic, but still aim for it. Also note that the type of website/app you are using to meet women may affect the amount of work you have to do.

  • “No profile” dating apps/websites. These are apps where people are choosing each other solely on photos, and there is no way to write a profile to express yourself. Examples include Tinder and Happn. You will typically need to spend longer chatting to women on these types of app to build comfort and attraction. 20-30 messages.
  • Profile based dating apps/websites. Examples include OK Cupid, Plenty Of Fish and Match. A well worded profile will build attraction for you (in a greater way than just having good photos. An attractive guy who’s profile is very beta will kill her attraction). You have a head start on the “No profile” apps and can spend less time chatting. Your only role is to maintain the attraction and make her feel safe meeting you. 10-20 messages.

By messages I don’t mean long winded emails. Each message might be a single sentence or even just an emoji. When you read my strategy below you’ll see what I mean.

When to message

Is there an optimal time to be messaging? I don’t pay too much attention to this, but here are some things to consider:

  • I tend to get Tinder matches on the weekend, Saturday and Sunday mornings. I’m guessing girls have been out the night before and still not met the man of their dreams, seen other couples, are in bed hungover, or are just bored.
  • Evenings. After work is an excellent time to message, the later the better. If she’s thinking about you right before she falls asleep it can only be a good thing. Usually people are less busy on evenings earlier in the week, so message Monday and Tuesday evenings.
  • Early morning. I tend to respond to messages when I wake up in the morning, before work. In London, a lot of people are commuting between 8 and 9, and a bit of a flirt relies the monotony of the commute. Only problem, the chat may be terminated abruptly when she gets to work, so be prepared to wait until lunchtime or the evening to resume.

In other words, there is no ideal time to message. Learn the patterns of each girl you are talking to and make decisions accordingly.

Your mindset

When you first begin to push for a first date within hours of getting a response from a women, you may start to feel uneasy. It feels different and wrong. It is scary. Your mind will tell you that you are more likely to be rejected and should prolong the messaging phase to avoid the pain.


You must be totally outcome independent. That means you don’t care if you are rejected (and as I said before, you will get rejected, many, many times). You shouldn’t care if you get rejected because you are an Alpha male and you know you have an abundance of women in your life (even if this isn’t true yet, you must believe it will happen).

Learn not to take rejections or flaky behaviour personally. Accept it. Embrace it. Meditate on it if you have to. Then move on.

Some techniques to help you do this include:

  • Breathing. Take five deep slow breathes before you act. Does what you are about to do/say still feel right? If so, do it. If not, don’t.
  • Understand they are rejecting your approach, not you. They aren’t rejecting you as a person. They are only rejecting the image you have projected to them. You cannot control how others will react so stop trying. Let them feel and do what they want. But keep your shit together and get on with what you want to do. If one girl doesn’t respond move on. This is why you should always be talking to as many women as possible, to stop you obsessing (us guys have a natural tendency to latch onto the first women that gives us a little attention. You MUST stop yourself doing this. Weirdly, the less you care, the more success you will have.
  • Get back on the horse. There are thousands of women who would LOVE to go on a date with you. Go find them instead of crying yourself to sleep over the one women who didn’t want to meet up.

Getting the strategy down

You’ve got the mindset down, and you’ve got a match on Tinder or Happn or any other dating site and the conversation is flowing. It’s time to convert your online chat to a first date.

Step 1: Get her off the dating app/website

After about 10-20 back and forth messages (keeping them short, 1-2 sentences each) you are going to move her from the website or app to WhatsApp. You can use another messaging tool, but I prefer Whatsapp.

Why WhatsApp?

At this point you are probably wondering why bother moving her to another messaging system. I do it for several reasons:

  • Compliance. You want her buying into your frame. You take the lead and she follows. When people do something small for you, they have been shown to follow a more advanced request later (such as meeting you for a date). The leap from App -> meeting for a first date is fairly large. Moving from App -> Whatsapp is a smaller request, and makes WhatsApp -> first date seem that bit smaller of a jump.
  • Commitment levels. She has to take the time to copy your number from the app, add it to her contacts and then message YOU telling you her name. Plus she gets that little nervous flutter you get when you first message a girl, wondering what to say. You’ve forced HER do an approach on YOU! You are setting yourself up as a prize and she is chasing you. How many other men do you think do that to her? You’ve already set yourself apart.
  • Confidence. You’ve subcomunicated to her your dominance and confidence. You are essentially saying “Look, either you move to WhatsApp and we chat, or you don’t hear from me again. Your choice.” That is outcome independence at its best. NO other guys are doing this to her.
  • Join her inner circle. What type of people do you think she has conversations with on Whatsapp. It’s typically reserved for people she knows well, like friends, family and boyfriends. It isn’t for people who she just met online. Once you reach Whatsapp you are once again building comfort, because if you are talking to her on Whatsapp you must be a like a friend or boyfriend.
  • Deleted. Once a women has found someone she will delete her online dating profile. If you were mid conversation when this happens you’ve got no way of contacting her. If she has your number, and the guy she’s dating doesn’t work out, she may want to get back in touch with you. She’s unlikely to re-create an online dating profile just so she can seek you out, but if she has your number in her phone the probability is higher.
  • Change of scenery. Moving from dating app/website to WhatsApp is the equivalent of the classic venue change technique used by top notch seducers. It provides her with the illusion and experience you’ve known each other longer that you really have, because you’ve taken her to different environments.
  • Speed. Remember, the point about chatting is simply to get a first date fast? WhatsApp helps you do this because it is more real-time than SMS or the online dating apps and she will feel more obligated to respond immediately, or within a few minutes, unlike other systems which can take hours. This keeps the interaction flowing and increases your chances of getting a date.
  • Avoid being lost. An attractive women will receive tens of messages through the online dating platform every single day. Weeding through them is no doubt a nightmare. If you don’t respond for a couple of days because you’re busy, she may have either started chatting to someone she prefers, or simply forget to reply. Moving away from the dating platform’s messaging system will ensure your messages get seen, and likely read.
  • Read notifications. Whatsapp tells you when she was last online and if she’s read your message. You can gauge her interest levels by how quickly she responds.
  • Extra info and photos. Another reason I like WhatsApp is it gives you an additional photo of her, and allows you to further gauge her attractiveness. Another tip is to copy her telephone number into the Facebook search. 50% of the time this will reveal her profile, giving you more information about whether she is someone you want to date or not, as part of your screening process. For example, if her Facebook photos showed her smoking, I wouldn’t go on a date with her because I don’t date smokers. She might not have mentioned that in her dating profile. You can also get a sense of her personality from the messages she posts and activities she gets up to. I’ve used this technique before and discovered the girl I was going to meet was using a different name online, and I could tell from her photos she was not emotionally stable. That saved me a lot of grief and trouble down the line. (P.S. the women will do the same to you if she’s smart, and you should be cool with that).

The Transition Request Message (TRM)

Now you know why you need to transition, let’s discuss specifics. It’s really not that difficult. Simply tell her you want to move to WhatsApp and give a reason. Don’t ASK, just lay out what you want to do and then wait.

The TRM should be comprised of 5 parts:

  • Closure to your previous conversational thread. You should initiate the transition on a high point, ideally when you are back and forth messaging rapidly. Don’t do this if you haven’t heard from her in days. Complete the conversation with a funny line.
  • Your request to move to WhatsApp. Lay out what you want her to do.
  • A reason why you want to move. The because is important. Studies have shown that when asking someone to do something for you, giving a reason, no matter how illogical is seems, makes people more likely to comply.
  • Your number. Just put it. No explanation necessary.
  • Your name. Give your real first name. This isn’t strictly required if you are on an app like Tinder or Happn that already show it, but I include it again just in case. You MUST do it if you’re on a dating site that uses usernames. It builds comfort, and for practical reasons she needs to save you in her contacts under something. More often that not her initial message to you on WhatsApp will be “Hi Jack. It’s Emily from OK Cupid”.

Putting everything together, here’s what some good and bad TRMs looks like:

Good TRM example 1

  • Closure: “And that’s why I’ll never ride an elephant again!”
  • Request: “Let’s move to WhatsApp.”
  • Reason: “I don’t always have notifications turned on for Tinder.”
  • Number: “07780123456″
  • Name: “- Jack”

Good TRM example 2

  • Closure: “Haha you make me laugh :)”
  • Request: “Let’s chat more on WhatsApp”
  • Reason: “because the messaging system is a bit rubbish on here.”
  • Number: “07780123456″
  • Name: “- Jack”

Both examples are fun, outcome independent and non-needy. You haven’t asked her to message you or if she wants to Whatsapp. You are an Alpha male and you LEAD. You expect her to follow. If she doesn’t message, you don’t care because you have other women in your life. Chances of success? 80-90%.

Bad TRM example 1

  • “Are you OK if we chat on WhatsApp? Please message me on 07780123456.”

This is an example of what NOT to do. You are supplicating and indicating nervousness by asking if she is OK with something you want to do. It’s needy, and unlikely to work. It comes across as though she is the only women who has ever chatted with you and you are pleading with her to keep talking to you. You’ve also forgotten your name, and haven’t closed the previous conversation. Chances of success? 20% (I totally made up that stat because I never send a message like this!).

IMPORTANT: Please, PLEASE do not abuse her trust in giving you her number by acting like a man-child. Do not spam her with messages or send abusive and threatening messages if she doesn’t agree to date you. I shouldn’t have to say this but some men are idiots.

What if she doesn’t message me back?

Most women will message me within 24 hours of the transition request. If you haven’t heard from her within this timeframe a couple of things might have happened:

  • She’s messaged you through the dating platform. Chances are you have done something wrong and she doesn’t feel comfortable giving you her number. At this point you need to decide whether to quit talking to her and move on, or build some more comfort and try again later. Unless there is a good reason to, I would move on. She may just be online to socialise and has no intention of meeting up with anyone.
  • She’s not that interested. Move on. There’s nothing you can do.

Step 2: First Date Proposal (FDP)

Once she picks up the conversation on Whatsapp, save her name and number in your address book, and continue vibing. You’re all set to make your next move – the first date proposal.

At this point, it’s best to keep up the momentum and pitch the first date during the first conversation, within 30 minutes of chatting to her on WhatsApp.

woman checking phone

If the conversation is flowing, go for it as soon as possible. If you get a sense she isn’t that in to you, build some more comfort by asking about her, before proposing the date.

If you or she is naturally a busy person, you can extend that timeline. Respond when you can. If she takes 20 minutes to respond, mirror that timing.

WhatsApp is more of a real-time chat than SMS (hence why I like it). You can see when she is online and has seen your messages. Therefore, once you get her into conversation, keep responding! Don’t wait. She has her phone in her hand and wants to talk.

How not to propose the first date

Here’s what most men do, and what you should never, EVER do again:

  • Don’t ASK her if she wants to meet up. “Would you like to come on a date with me?”. This is beta. You must have the attitude that you are AWESOME so OF COURSE she wants to meet up with you. You’re the prize here.
  • Don’t ask if she’s free on one particular night. You are boxing yourself into a corner by doing this. She will either say “I’m busy”, then you don’t know if she is lying or telling the truth. You also then have to pitch again (“How about saturday”) and you start to look desperate. You’ve asked twice and are at her mercy.
  • Don’t beg. “Please come on a date with me. It’ll be fun I promise!” Of course it will be fun. The only people who say it will be fun are guys who think it won’t be fun. You are not a salesmen. You are an Alpha male who goes on dates with hot chicks all the time.
  • Don’t worry too much. You have to give the impression you do this everyday (and trust me, you will be able to if you follow the guide). Who cares if she says no. She needs to feel the laid back, confident vibe emminating from you in all your interactions. It will increase her attraction to you.

How to correctly propose the first date

When you’re ready to propose the first date, do it in a similar fashion to the transition proposal. Don’t ask, state. Expect it to happen.

Here’s a great line I learned from I use all the time because it flat out works. Ask:

  • “What’s your diary looking like next week?”

As with the transition message, you should ask this as part of an on-going conversation, not randomly out of the blue.

Notice how you haven’t asked her on a date. But you are implying that you are about to ask her out. It’s highly unlikely that she will respond with “I’m busy everyday next week” because that sounds like bullshit. Very few people have plans every night of the week. It is possible though, but only expect that response 5% of the time.

The only exception is if she is about to head away on holiday. If either of those situations occur, I will say “Cool. Let’s catch up when you get back / next week”. Again, I’m not asking. I’m telling her what is going to happen. She will normally agree. Then don’t contact her until she returns, and meanwhile move on to setting up dates with other women.

When I don’t use the line above, I’ll go with something like “Where in London are you based? I’m not a fan of overly long messaging back and forth so let’s meet up in ‘real life’ (scary I know) and find out more about each other”.

Again, notice how I am not phrasing it as a question. I am giving an excuse to meet in real life (because I don’t like lots of messaging) and am just saying “if you agree that long messaging sucks then you should come on a date with me”. Her response is typically “I’m in X, let’s definitely meet – not a fan of long messaging either”

At this point, she will generally respond with nights she is busy and nights she is free. She knows you are about to ask her out, so will make it clear when she is available.

Good example 1

  • Me: “What’s your diary looking like next week?”
  • Her: “Weirdly I am free every night apart from Thursday. I have mates I promise :S”

Notice how she is QUALIFYING herself to you already! This sets an awesome frame for the first date.

Good example 2

  • Me: “What’s your diary like this week?”
  • Her: “Not much!! Friday my flatmate will invite some friends over… Thursday I have a late meeting that I found out yesterday… But weekends off! You?!?”

Good example 3

  • Me: “I’m keen to discover where to find myself a pink dress and think you might be the girl in the know 😉 What’s your diary looking like this week? – Jack”
  • Her: “ Haha I’m glad I inspired you with my dress. I’m not working this week so I’m around…?

Bad example 1

Here’s an example of what not to do:

  • Me: “Good to meet you last night. Are you around tomorrow (wed) eve? I’m in the area until six if you want to meet after work for a quick drink”
  • Her: “Can’t do tomorrow unfortunately, would Thursday work?”

Notice how I only gave her one option to meet me and she was busy. Luckily I had met her in a bar, not online, and she liked me enough to give me a second chance by suggesting Thursday instead. Most girls, especially if you haven’t met them in person won’t do this and will make you suggest another day.

Also notice how my message isn’t as dominant as the previous exmaples. I’m asking her if she wants to meet me. The saving grace was me saying a quick drink which implies I don’t have time for anything longer and am not going to act needy on the date.

Once you know which days she is free, pitch the date. Remember to keep it non-needy. Just suggest a drink on a date she is free.

If you know she lives close by I always get her to come to near me because I know the bars.

  • “Let’s grab a quick drink Monday in [insert my area of London]. 7pm work for you?”.

Tell her you are getting a drink together. Give her the option of a time.

If I don’t know where in my city she lives in, try:

  • “Let’s grab a quick drink Monday. Can you get to [insert my area of London] easily?”

If she can’t, figure out where she is based and meet in the middle. Some guys would argue that you should arrange the date close to yours so you can take her back to yours on the first date. I generally only do that on a second date so I don’t mind if we aren’t that close.

(Top tip. Have a bar that you go to regularly near where you live and get to know the bar staff. Now when I walk in on a date the bartenders often say hello and shake my hand. When the women I’m meeting sees this it flips her attraction switches in a BIG way. It implies I go out a lot, something which subtley subcommunicates I’m not looking to settle down into a monogomous relationship anytime soon. It also implies I am known, respected and have some sort of status in that domain, all things that women LOVE their man to have. Watch the film Legend with Tom Hardy when he goes into one the clubs he owns with his girlfriend. Every guy shakes him by the hand and every women takes notice)

After the first date proposal, she can either agree or disagree. If you’ve done everything right she WON’T disagree. If for some reason she won’t agree to meet you then consider moving on. She’s said she is free, and you met her on a dating app, so there is something else going on.

The one issue she will have is location. If she wants to meet nearer hers – be careful. You are buying into her frame and she is not putting in any effort to meet you. However, if she sounds very keen and you suspect she wants to be close to hers so you can take you home that night for sex, obviously agree to meet.

As a rule, first dates are on my terms, in my neighbourhood (because I can give the women the best experience). Be the man. Take charge.

Once the date is set, continue on with your original chat for a brief while to prevent buyer’s remorse. Don’t act like your won the lottery and spam her tens of smiling emojis though. You have hot women asking you out on dates every night remember! (Feel free to dance around your house fist pumping the air though, just as long as no-one else sees).

A complete example

  • Me: “What’s your diary like this week?”
  • Her: “Not much!! Friday my flatmate will invite some friends over… Thursday I have a late meeting that I found out yesterday… But weekends off! You?!?”
  • Me: “Let’s go for a drink tomorrow evening, just a quick one after work as I need to be somewhere later. Do you end at 6?”
  • Her: “Can I confirm tonight with you? Because I’m supposed to meet my friend but she hasn’t confirmed yet”

(She confirmed later that day and the first date happened)

What if I get some another response?

If everything has gone smoothly you should get a good response. But occasionally you may encounter the following:

  • She responds but doesn’t answer the question. This happens 5-10% of the time. It’s annoying. Do you follow up and look needy? Do you not response until she rereads your message and replies with when she’s free? Or do you take it as a sign of disinterest and move on to the next women? I don’t have an answer to this. I would suggest it means she isn’t 100% convinced about meeting you yet, but is still attracted and the opportunity is still there. Wait 30 minutes to an hour and if she hasn’t sent another message, it’s time to try again. Don’t get needy and start chastising her for not answering the question. That’s not cool. Remain laid back and confident. She may just need a bit more comfort chat to build some rapport.
  • She asks why you want to know. Respond “So you can come for a drink with me ;)” and then see what happens. If she responds in any other way than telling you when she is available, move on. You did something wrong early in the messaging game.
  • She doesn’t respond at all. She doesn’t want to meet up. Don’t message her again. Move on to the next girl.


In order to maximise the number of first dates you go on when online dating, you must act fast. Move a women from the dating platform to WhatsApp then propose the first date in a non-needy way. Remain outcome independent and don’t ever get hung up on one woman, especially if you haven’t ever met them in real life.

The process is simple when you get the hang of it, and your success rates will improve dramatically. Not only that, but you will have set a Alpha male frame going in to the date and she’ll be looking forward to meeting you.

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