Do you have problems escalating on dates with women who are shy?

A lot of men tell me if a girl is shy, they don’t know what to do and feel uncomfortable “making a move” in fear that this will make the girl feel uncomfortable, so they play it safe, stick to conventional topics, avoid touching and at the end of the night get a quick kiss on the cheek if best.

And then they rationalize - well, the girl was shy, there was nothing I could do there.

Recently I had a few back to back dates with women who were pretty shy and yet still by the end of the night we were either kissing or going back to mine. So let me tell you in 3 steps how I handle my dates with shy women. And the last step is one of my favourite techniques to make all of this work.

Step 1 - Realize they are there for a reason

Sometimes shy women won’t give you many attraction signals, and a lot of guys start doubting if the girl even likes them.

If a girl came to see you, that in itself is a massive signal of attraction since most attractive women don’t go on dates just because.

Especially if you approached her in real life and talked to her before, that conversation made her like you enough to show up on a date with you.

So even if she is a bit cold and stiff at the beginning of the date, it doesn’t mean she doesn’t like you. It usually has to do more with how they are than with how you are.

In my experience the reason a woman is shy is because of her own insecurities. Maybe she was raised in a conservative country where women are judged for “going too fast”. Maybe she has been rejected before and that affected her a lot, and her own ego is trying to protect herself. Maybe she just doesn’t have a lot of experience on dates and doesn’t know what to do.

These are usually the real reasons rather than how she feels about you, especially if she is cold in the first part of the date.

Step 2 - Don’t wait to escalate

A lot of guys make the mistake of assuming they shouldn’t escalate with girls that are shy. They conclude that these girls go slow and hence you need to spend hours chit chatting or have 2 dates before you can kiss and other foolish assumptions.

The real reason guys don’t escalate is that they fear getting rejected, so they try to delay the escalation in hopes of minimizing the rejection.

Look, if you want to wait for 3 dates to kiss a girl, you can do it but if a girl feels you want to escalate things with her but don’t, that’s not an attractive behaviour. Also if you keep things logical with no flirting, chances are you won’t even get to the 2nd date.

So escalate just like you would on any other date. The difference with other dates is that with shy girls - there will be more “rejection” in the beginning.

You might try to sit next to her and she will move back. You might take her hand and she might take it back.

Most men think this is bad, but actually these mini rejections are good if you know how to handle them. If you do it the right way, they actually help you in the escalation process

Step 3 - Break the 4th wall

A lot of you might be thinking - dude, if the girl doesn’t want to be sitting next to you, you shouldn’t try it, you are making her feel uncomfortable.

What actually makes girls uncomfortable is you being uncomfortable around her. If you want to do something but hesitate, send mixed signals - these things make her uncomfortable.

As illogical as this sounds, her mini-rejecting me makes her more comfortable. Here’s what I mean.

Usually shy girls have trouble expressing their emotions and feelings in general. So when she pulls away when I try to sit next to her, rather than being frustrated or hurt by this, I smile and just say something like “so you are going to make it difficult to flirt with you tonight. It’s okay, I like it”

By saying this I break the 4th wall and verbalize what’s happening. After I do this a few times with different variations, they usually feel more comfortable verbalizing their own feelings. And then they usually tell me that in their country this is not something that usually happens, in her past dates this is not something that usually happens or something similar. But the underlying message is she likes me escalating, she is just not used to it because of her past experiences.

And what happens to a human being when they verbalize their own feelings in the open? They get more comfortable

This is the key. When I try to sit next to her, I don’t even care that much if I end up sitting next to her or not at that specific moment. What’s important is that I want to make her comfortable enough to express her own feelings.

And when she pulls away, sees me unaffected by it, and then I even verbalize all of what’s happening - the shy girl opens up, starts expressing her emotions and the ice curtain starts dropping.

And once this moment happens, usually they are not shy anymore and start reciprocating on emotional and physical escalation.

You can do the same thing with emotional escalation - if you just get the shy girl to open up emotionally, that will also help a lot to get her more comfortable.

And do girls like this? Many women have told me or sent me a text message afterwards thanking me for helping them open up. Some have even said that they see themselves differently because of our experience together and they feel “more liberated” from their past chains of cultural judgment or judgment from past relationships. So in a way, you’re actually doing them a huge favour which is my favourite thing about this.

Calibration

A quick disclaimer - if you haven’t dated a lot and are more of a beginner, I would advise you don’t try this yet and go a bit slower.

Carrying out stuff like this with shy women requires quite a lot of calibration on your part and knowing when to escalate and when to pull away, otherwise yes, you can risk making the girl too uncomfortable.

But if you are more advanced and have the basics of flirting and escalating down, feel free to try this.

It’s not something I read in a book or post, I just naturally practiced this sequence with shy women. And after it worked many times I noticed these patterns and put it in my own words.

And if you happen to date a lot of shy women and don’t want to go on 3 dates before making a move, this could be a good tool in your arsenal.