August 23

Stop overthinking: Here’s how to do texting between your second and third date


If you’re an evergreen like me, and you’re suddenly faced with someone you’re interested in, things can feel scary.

Really, really hairy.


You start overthinking every text message you send her. And if she doesn’t reply in 12 hours, you think,

It’s up. I’m dead.

She’s gone.

Relax, you don’t have to overthink every single aspect.
Relax, you don’t have to overthink every single aspect.

How do you progress to the next date, and the next, and the next, so that she eventually comes to become your girlfriend?

We speak from experience, not expertise

Know this. We aren’t the kind of guys that have a long track record of dating.

For most of school, we were nerds, studying.

And for most of the advice given here, it’s given by men who’ve struggled.

Understand the life cycle of a date

Dates can be like buying shares on the stock exchange. Come again?
Dates can be like buying shares on the stock exchange. Come again?

If you think about dates, you would realise why dates, can be a little like buying a stock. Yes, I’m talking about those shares listed on the stock exchange.

Of course, your date is not a stock. This is an analogy.


Imagine you were a trader that traded stocks daily.

You’ve a pretty good idea of your investment philosophy.

And you go and buy it. In this case, you go and meet someone whom you think will match.

But not every stock you buy will turn out to be a winner. In that case, you end up selling them.

In fact, in the first few days, you will experience fear as you see the markets gyrate.

In much the same way, even during the first date, if you felt great, and you saw her laughing to your (lame) jokes, you may still be fearful of moving it past the initial meeting.

How do you move past the initial meeting to something richer and fuller?

Be clear after the first meeting

From my conversations with others who have dated, and successfully moved past the first date, to the second, to a relationship, they tend to be clear.

If you’re interested, say something like,

Hey, I really enjoyed your (quality), where you (follow up with an example).

I’d be interested to meet you again. Would you?

If you’re scared, I get it. But being mixed in your signals, and expecting the lady to read your interest is not the best. Hiding your interest behind the phone of a screen, can be a cop out for what dating ultimately is – courage and valour to go for what you want.

From what I’ve seen, ladies do prefer men to take the lead, and to show interest.

See the inherent good in the date

Yes, you’re going to be scared of what the date thinks of you, especially if you feel positively towards the person.

And you might be scared she’s going to ghost you, and disappear.

But think about it this way. If your date ghosted you after the first meeting without explaining, that might reflect more poorly on her, than on you. Especially if you didn’t do anything criminal.

You might have been insensitive in the way you texted her. But good, emotionally mature people know how to draw boundaries, and say,

Hey, that hurt.

Why not assume this?

What if your date was trying the very best she could?

Go after those who show interest

Chasing dates who just aren’t interested just wouldn’t work.
Chasing dates who just aren’t interested just wouldn’t work.

Recently a good friend told me,

If someone is not interested, even if you play a perfect hand, it’s not going to work.

On the other hand, if someone is interested, love covers a multitude of sins.

Yes. Even during the beginning, when you’ve barely known the person for more than the 2 hours that you’ve first met.

If that person is interested, whatever you do might be read with curiosity and openness, rather than just suspicion and ill feeling.

I’ve been there. Where I’ve spent hours thinking of the perfect message to type, sent it, and then seen the lady saying,

I’m uncomfortable going out on a walk with you.


I’ve prayed and don’t think this is the right thing for me at this moment.

Yet on the other hand, when I’ve screwed up badly with messages that seem insulting and insensitive, dates have come back and followed up over and over again. This isn’t to boast.

But it’s to say one simple thing.

If someone is interested, it will be both parties trying.

So why do we find it so hard to believe this? Why do we find it so hard to believe in the beauty of mutual attraction? Why do we force ourselves to chase people who are not interested in us?

Why do we believe ourselves so unworthy of love?

Our childhood traumas remind us of pain

I confess. I’m that guy who over-reads … everything. If you’ve taken more than 16 hours, I think

I’ve been found out as the imposter. I’m dead. This is over.

You too?

High five.

But if we look at our past, we will see signs of where we’ve been abandoned and thus hurt.

We bring that hurt forward.

The time when mummy left you at the childcare and came late. Or when Dad told you that you just had to hold his hand, but ended up losing you at the crowded mall.

Or the time when you were 15, with your first love, and she just disappeared. One day you were friends, and the next day you were not.

Understanding that won’t make you feel immediately better, but it offers clues to help you to feel a greater empathy and compassion for the wreck you currently are.

Don’t label yourself. It can cause more pain than good.
Don’t label yourself. It can cause more pain than good.

Keep breathing

Telling you not to overthink is going to be tough. Because yes, we know that feeling. Where you are analysing how long she’s taken in the past to reply your message, and then you look at the current interval of non replies, and you think the game is up.

You’ve offended her, and it’s over.

Or you try to read and re-read the subtext of what she says, and you wonder if you’ve missed something.

You find yourself slowly unable to concentrate on the work.


It’s going to be alright. Dr Val Gonzales, my therapist for the past 6 years, deals with people struggling through their emotions by teaching them this framework.

Trigger – thought – emotion – action

The key is being aware of the thoughts running through your mind, and reframing them. For example, you might say:

What you think Reframe it as
She’s not replying me, I’ve screwed up big time and lost her. I’m learning how to be more patient with my expectations of reply speeds
I’ve said something wrong I’m learning how to speak more sensitively

Knowing these principles, here’s what you can do better.

Arrange the follow up within a week

If you’re interested in her, take the lead. Meet her in the week. If she is attracted to you, she would reciprocate. My understanding of dates is that if they are interested, they are willing to meet you once a week.

It also offers a healthy space between dates for you to start longing for each other. You definitely don’t want to be bored of each other.

Text as you would a friend

Don’t let the conversation die a slow death like your potted plant.
Don’t let the conversation die a slow death like your potted plant.

I’m not a texter.

My frequency of replies is 3 days. On average.

Don’t follow me.


You will lose all your dates that way.

If you can have a conversation with your date about what is the frequency she expects, have it. Ask her, “what are your expectations around texting?”

But it’s also vital to stay in regular contact. There are no rules around this. But some helpful guidelines:

  1. Show care – if she says she has an exam or big meeting, wish her the best in the morning.
  2. Ask her about what’s important to her
    1. In the first date, probe for ideas around what she enjoys. Talk about those things.
    2. Mix emotional contrast. Don’t talk about heavy things all the time.

Be yourself

And as much as this is cliché, be yourself. If you end up someday with her, you won’t find a healthy marriage built upon a mirage of who you actually, really are.

This applies to all things. If you won’t spend 12 minutes looking through the chat history, scrolling and scrolling to find signs and clues of why your date isn’t replying for friends, then don’t do it for her.

She is special. But hold your horses.

Concentrate on a life outside of her too. She isn’t the only thing that’s important. Your career, your purpose. Your goals.

All these are important. And ladies like men whose focus isn’t just them, but on a bigger, wilder adventure.

Because they know that the life they will lead with this man won’t just be a boring adventure spent on the couch pigging out with Netflix, but on a meaningful and purposeful one.

This is hard. Don’t get me wrong.

Especially when you’re unused to dating, having a girl finally show interest in you can feel like the wildest thing that you need to work hard at.

One way is to pray and commit it to a God. Knowing that there’s a greater being in control can help you rest your faith. But if you are agnostic, write a letter of love to yourself. Each time you face fear and anxiety around the date, catch the thought, and reframe it.

You’re really, really worth loving

It can be hard for you to believe this.

But I want to say this,

you’re worth loving.

And only you can believe that for yourself.



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