How a software developer almost gave up on his dating life

I want to tell you a real life story that illustrates why it’s important to keep going through the rejection storm and what good can come out of it.

A few weeks ago I was going out during the day with a guy who is a very serious, analytical software engineer. This was our 3rd session together.

For context, he had never done cold approaches during the day before so during the first 2 sessions we got him to deal with approach anxiety and learning how to properly stop and open, and the goal for the 3rd session was having longer chats with women and trying to get phone numbers.

Anyways, he starts off pretty rough – 5 approaches and all complete rejections where girls are just completely walking past him and ignoring him.

He hadn’t experienced this kind of rejection storm even during his first 2 sessions, so he is becoming visibly even more nervous which in turn makes his body language and tonality way worse.

I can see that his subconscious mind is trying to ‘protect himself’ from the rejections by making him speak quietly, avoiding eye contact and trying to become invisible.

Big problem.

I’m telling this to him, so he is aware but that obviously doesn’t help much because even if you’re aware of it, it’s quite hard to fight your subconscious mind.

So I tell him two things:

One – let’s go back a step. The goal for this session is not anymore to get numbers or chats but simply being able to stop a girl and giving her a compliment.

When you break down a bigger goal into smaller goals, it’s much easier for you to achieve them – same in dating. And if a goal is making you way too nervous and paralysing you into not taking the best action, it’s good to break it down a little and take it slower.

Two – more importantly, we need to take this session as a learning lesson to learn how to deal with rejections and not to see them as something negative.

I ask him – “What are some good things about getting rejected?

He doesn’t really have a clear answer. So I tell him –

Look, many things.

It means you’re taking action in the first place. Which is the most important thing in this process.

Also every rejection gets you closer to meeting your dream girl.

Also it builds your mental strength and fortitude you will need in your life when really big problems come and sh*t hits the fan.

Also it’s good for learning how to deal with rejection because you need to be okay with it (rejection) to be a cool, attractive guy girls will like. So be grateful you have a chance to practise it”.

Anyways – for the rest of the session he keeps getting mostly rejected and even though my pep talk helped a bit, I’m still worried how this is affecting him.

At the end of the session, I ask him how he feels.

He says this definitely was the toughest session so far and he’s not sure if he can do this.

I tell him to go home, make some nice meal for himself to celebrate his achievement (because no matter what – he pushed through today), do the homework I gave him and I will see him next week. It will be another day.

He agrees.

I meet him 7 days later in the exact same spot.

We spend a few minutes talking about his week and how he’s feeling.

He says that he feels more nervous than before because of so many rejections he got last time.

You did great last time and most importantly you showed up today. If you keep going, results will eventually come sooner or later” – I’m trying to encourage him.

We do the warm up exercises and it’s time to start approaching for real.

We see a beautiful girl walk past by us and I tell him to go.

He goes in and sort of stumbles through the approach.

I’m thinking this will be a quick rejection – but no. She actually stops and they start talking.

I can hear through the microphone that he sounds quite nervous (as it’s his first approach of the day) but it’s slowly going away.

His voice is becoming calmer and louder.

The body language slowly relaxes.

They are talking for a few minutes already and they seem to have a pretty good vibe. I’m already super happy for him.

Then she says she’s actually going to a museum right now and she has an extra ticket. BINGO.

It’s turning into an insta date.

He is becoming slightly nervous again because he has never been so far in the interaction but he deals with it well and they start walking.

I’m texting him trying to encourage him and give him some sort of game plan.

I give him some conversation topics, ideas on how to flirt and what to do after the museum.

Most important thing for him (as with many guys I work with) is to show intent and be flirty so I send all caps


Finally I tell him:

Most importantly, enjoy this! This is why we do this – to make new connections with women we like and have adventures like this that hopefully go somewhere. Enjoy the moment!

I watch them enter the museum and his mic disconnects.

I’m walking back home extremely happy and proud of him eagerly waiting to find out what happens.

Then I realise that no matter how it goes – the most important lesson here is that a lot of bullsh*t we face trying to improve our dating lives will only have value in hindsight.

What do I mean by this?

All of the rejections he faced the previous week – it didn’t seem like they are worth anything.

But after today – they are what made him into a guy he was today and got him this amazing adventure with this girl.

If he had quit after the 3rd time – he wouldn’t have this date.

So that’s what I want to leave with you here – improving your dating life is hard. It’s challenging.

But if you quit – you won’t get the payoff of these challenges.

So keep going.

Hope this helps.

Any questions – let me know.

Other articles