Men – How to Flirt via Texting to get a 1st or 2nd Date

By June 19, 2019 Advice for Men, Blog

Men, how to flirt via texting to get a 1st or 2nd date!

Let’s say you have met a woman at speed dating, a singles event, online dating or in real life and arranged to meet.

What you do next matters and will determine if you get a 2nd date.

Too often men get the date and don’t do anything in-between arranging the date and the actual date.

This the number one reason men don’t get a 1st or 2nd date!

I know you are focussed on the outcome of getting her on a date and see texting as a way to arrange that!

But texting is so much more!

When you flirt by texting you are  building your connection with her and if you miss this step, it could be where you are going wrong.

Instead of focusing on the end game, it is important to flirt with her by text to build the connection in the meantime.

Believe it or not, being able to flirt by text message will make you irresistible to her.

Think of being able to flirt via text as being like Sales!

The best way to get someone to buy something from you is to show them the benefits first!

This is what you are doing when you flirt and are playful via text.

The number one thing most women are looking for is the guy who can make them laugh, who has a sense of humour and who is fun. That is why it is important to show her that side of you by being able to flirt by text message.

When you do this, she will look forward to your messages and she will also look forward to hanging out with you.

Attractive women often have more than one guy who is interested in them so it is important to be in the front of her mind and stand out from the rest in the right way.

Texting is a simple way that you can do this.

It allows the girl the opportunity to see you as fun and to be able to see herself enjoying your company. If she can’t see herself enjoying your company, she is not likely to go out with you.

You can start this from the beginning with the very first message you send.

Maybe you don’t know how or you have been caught in the ‘playing it safe’ trap.

It will take some practice and seeing what works for you and your personality.

But no matter what your personality is, it is time to stop being boring and to stop sending boring messages.

I realise that your main purpose of texting will be to get her meet you face2face but to successfully be able to do this, you need to first work on building the connection and triggering her emotions.

You can easily do this by using texting to flirt with her and make her want to meet you! In sales terms you have a warm lead!

How to Flirt via Text

Here is the how to flirt by text message!

Get rid of the small talk and pointless conversations. Like ‘Hey’, ‘How’s it going’, ‘What’s happening’.

Women get overwhelmed by these messages and they are pointless as they don’t build a connection or encourage a conversation.
Stay away from the formal, the logical and the plain boring.

The whole ‘tell me about yourself’ is off putting, boring and too loaded with the possibility of saying things that either of you just don’t like.

Those types of conversations are better saved for getting to know each other down the track.

Those types of text convos rarely build anticipation or lead to a fun date. They don’t motivate the girl to want to meet you and that is what you are aiming for.

Remember if she can’t see herself having fun with you then she probably won’t go as she will do anything to avoid a boring and awkward date. In fact, she would rather binge watch Netflix!

Here’s what to do:

  1. Use something amusing from when you met or the last time you caught up.
  2. Try something funny from your day
  3. Funny take on a compliment

1. Flirt using something from when you met or the last date

When you met, you will have had a conversation and started to build a connection and attraction. Think back to what you talked about and there will be something that you could use.

Again, use something funny, unusual or interesting that you talked about.

You could continue a joke you shared together, mention what you are binge watching on Netflix, or the latest episode of that show you both like or challenge/admit defeat on something you debated.

This will help remind her why she chose you at speed dating or why she enjoyed meeting you.

Maybe on your first meeting you talked about travel and you remembered her saying something about traveling. You could text:

I have never been to Bali, I know I must be the only Australian who hasn’t gone! But now I am sitting at my desk daydreaming of going, you made it sound so good!  How’s your day going?’

You will get added brownie points for remembering what she said – girls love that you have listened to them.

Or you could try something simple like “Is it too soon for casual texting? After all, we just met!’

Make sure you have a question to keep the conversation going.

2. Flirt by being Funny about your day

What did you do today? Think of something that happened that was different, interesting or that was funny. There is always something that you can spin to make it fun, even the most boring things can work!

If you are having trouble thinking of something then maybe it is time to start getting out more or simply start to think outside of the box.

Many people simply say good morning, but you could put  a fun spin on it like:

‘Good morning. Another day, another dollar! Who am I kidding I wouldn’t get out of bed for a dollar. Have you got a busy day ahead of you?’

I will give you an example here with something boring to help you out:

Maybe you just had lunch, a boring text would be ‘Just had lunch, how’s your day going.’ It doesn’t create any sense of fun. But take that lunch and add something that is interesting, weird or funny and you get a better reaction.

Here is an example:

Instead of saying ‘Just had lunch’ you could say ‘So hungry today, gave in to the Jiffy van, I may live to tell the tale! How’s your day?’

Or ‘I just had a killer sandwich that felt like it was crafted by the gods… so good!

It allows the girl to play along with the conversation.

Here is how it could play out:

You: ‘So hungry today, gave in to the Jiffy van, I may live to tell the tale! How’s your day going?’

Her: ‘Ha, ha what delicious treats did you give in to? My day is great, went with the healthy boring salad option’.

You: ‘Gave in to a heart attack in a bag – a pie! It tastes awesome and beats your salad don’t you think?

Her: ‘Omg I totally agree, it’s cold and wet and the thought of that salad isn’t doing it for me. Although I will be able to tell the tale!

The 2nd one:

You: ‘I just had a killer sandwich that felt like it was crafted by the gods… so good! Hope your day is going well and your lunch it as good as mine?’

Her: ‘Thanks, day is delightful. Wow, where did you get it from, you are making me hungry!’

You: ‘I made it with my own bare hands, if you are lucky enough I might make you one, one day’.

Her: ‘Lol, so you are comparing yourself to the gods now!!! Good to know you don’t suffer low self-esteem!’

You: ‘You’ve worked me out and discovered my secret super power! Clever you!’

Of course, how it goes depends on the person you are texting and what you feel comfortable sending. It is playful, fun and not boring and will leave a smile on her face and looking forward to your messages.

One rule to remember is to always keep it positive and don’t put yourself down. The other thing to remember is to not bombard her with text messages, allow the 1:1 ratio for texts.

3. Flirt by using a teasing compliment

Women love compliments but this can be tricky. Often men give over the top compliments about superficial stuff or act too cool and won’t give any compliments.

Neither works well and will not get the results you want.

With online dating girls’ inboxes are often full of inane compliments like:

  • God, you are so beautiful .
  • You’re hot
  •  Why is someone like you single

Because they are so overused they seem insincere.

For compliments to work with someone you barely know they should be specific about them or they should just be fun and  you can use compliments that make you both look good.

Give her a fun specific compliment and include something cocky about yourself.


These are simply suggestions to help you be more creative, fun and flirty with your text messages. Remember it is always important to be yourself as that is what she liked in the first place.

Dare2Date is here to help you and if you are struggling knowing how to flirt via text messages, contact us by text or email to arrange some support.

Happy dating.

Debbie xxoxx

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