How cool should you play it with a pretty girl?

I made a TikTok today that got me thinking about something stupid I used to do when I’d meet a girl I was attracted to:

I’d play it cool.

Way too cool.

Not show my interest.

And miss out on her for it, even when the girl had straight-up APPROACHED ME!

Yeah, this led to many a regret and many a missed connection. College me had the right idea though, even if he applied it shoddily in the field:

You don’t want to come on too strong with your interest in a girl. You have to pace yourself initially, and let her “come to you” to a certain extent. Otherwise you risk getting needy and ruining the sexual tension.

The question isn’t WHETHER you should play it cool, OR show direct interest in a girl. You need to do both. But what’s the ideal ratio here?

When do you transition from one to the other?

Like all tactical moves in dating, CONTEXT determines efficacy. For example:

If I’m chatting up a girl sipping coffee at a cafe, I’ll express my interest pretty soon after saying hello and asking her how her day’s going. “I thought you were cute and felt like saying hi”. Whereas if I’m chatting up a pretty server at that same cafe, I’ll make some high-energy small talk, then NOT go in for the kill, at least not on that same day.

Going in for the kill and expressing direct interest with the cute customer would be bold, while with the cute server, it’d come off as needy and socially disconnected in most circumstances (at least until she’s more comfortable with you).

In the former context, expressing direct interest quickly works because:

1. It’s now or never, you don’t know if you’ll be running into this girl ever again. It’s BOLD to show desire for her and risk the sweet feeling of rejection instead of risking letting her go forever.

2. It’s socially calibrated. You have no reason to talk to this girl besides your desire to hold hands with her (after marriage), so you gotta be honest. She already knows why you’re talking to her! In this case, it’s actually NEEDY to hide your desire.

Whereas “long gaming” works in the latter context because:

1. You’ll likely see this girl again if you frequent the place. You have the opportunity to build sexual tension, mystery, and fantasy over a while. Let her feel the twinge of uncertainty. “Is this guy REALLY attracted to me or just being friendly?”

(then you can go in for the kill sometime down the line when it feels right)

2. Again, social calibration. You can afford to let her come to you. There’s ALREADY a contextual reason for you to be chatting each other up, so jump on it. Go with it. Showing direct interest way too quickly would usually mean coming on too strong.

So. General rule.

With some exceptions, you’ll have to hold off on showing interest and instead “long game” a girl you meet in a group context (ex. her work or yours, through your friends, at a social hobby), and “short game” a girl you meet one-on-one (ex. street approach, she’s a cute + very receptive stranger you chatted up at a party)

Have some awareness, gentlemen. The balance between being pushing and pulling, and how much of each to employ in a certain context, can take some getting used to. You have to show interest in the girl, but not be needy about it. You have to like her and desire her, but not come on too strong. You have to lead the interaction forward, but let her come to you.

Knowing exactly when to push a girl and exactly when to pull a girl is an intuitive feeling…

But maybe you’re disconnected from your intuition, or you ignore it. Maybe you fear rejection, and you’ll be like my past self for it – Not asking out the cute girl doing charity work who you serendipitously ran into again, even when she looked at you like a deer in headlights waiting for you to do it. Not jumping on the girl at the party who looked at you that same way, even after you’d already gotten her hooked and curious and sexually tense. Not asking the pretty beach volleyball girl for her number when you had to leave with your friends…

And forever regretting that missed connection.

What’s stopping you from moving things forward with the girls you like, or maybe even meeting them in the first place?

See me in coaching when you’re ready to tell your fears to fuck off, and live a dating life with no regrets.

– Ben

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