A Guide to Kissing on a First Date

The fairy-tale ending is just four simple steps away

Sten Sootla
4 min readOct 14, 2019
Photo by Alora Griffiths on Unsplash

The best thing in the world: sex. The second best thing in the world: a kiss. Absolutely the worst thing in the world: depriving yourself of the former by not going for the latter.

It’s hard, I know. Heck, the very first woman I dated at fourteen, it took me ten dates to muster up the courage to finally give it to her hard on the lips. That’s a whole month of four hour walks in -25 degree Estonian winter. To this day, some parts of mine are shrunk from the cold, if you know what I mean.

Ten years and hundreds of dates later, I’m an absolute beast though. Now the only action I take is lip action. Here’s how to make it happen:

Start the evening with a hug

A hug shows your date right away you mean business. Go in strong — confident and comfortable. Go in with a stable, steadfast walk, your back straight and arms wide open. Go in looking like a goddamn Japanese airplane doing a kamikaze.

And don’t forget to smile — from ear to ear — while you’re at it. I’ve found it best not to look depressed when trying to wrap myself around strangers. It’s weird, especially to someone you’ve barely met before. Instead, peer straight into their soul. Make an effort to exhibit the full set of your teeth. That’s charming, especially to someone you’ve barely met before.

Make physical contact throughout the night

The secret to a great first kiss is for it to be natural. It’s quite unnatural to touch someone’s mouth with your mouth before touching her arm with your arm. A great kiss must, therefore, follow a repertoire of finer maneuvers.

In general, you want to establish yourself as someone touchy without coming across like you have a fetish. You want to build up and slowly escalate physical contact throughout the night, to the point it feels awkward not to launch into a make-out session. Remember: physical attraction is best shown physically.

A hug was a great start, but a mere formality. The second touch is the magic one. It’s also damn cringe. Your best bet is to distract her while you’re at it, so the weirdness wouldn’t register. As if it’s accidental. Here’s a definitive list of field-tested techniques that don’t work:

  1. stretching your arm out on the table and praying for the best
  2. playing rock paper scissors, hoping you can envelop her rock in your paper
  3. palm reading

This works: casually brushing one of her body parts while getting up to have your bathroom break. You do the deed and immediately flee the scene so as not to face the consequences. Genius.

But how exactly do the logistics work, you ask? What if she’s simply out of reach to be poked? This brings us to the next point…

Sit next to her

It’s not often that I’m sexually aroused during a dinner date. One time, I low-key was. I could see she was, too. The problem: a hard, long piece of wood between us. No, not that… A table, of course.

Forget fancy restaurants. Forget stools. What you’re looking for is an intact piece of material that allows you to slide closer to her covertly. A park bench. A picnic blanket. Perhaps a small boat with bench seats. Whatever. My last date was at a bar on a couch. We kissed.

I’ll throw in a quick FREE guide on choosing which side to position yourself on. Pimple on the left cheek? Sit on the left. Pimple on the right cheek? Sit on the right. Pimples on both cheeks? Sit at home until you’ve got that shit taken care of.

Be willing to lose her

You’re comfortable with each other. You’ve hugged. You’re touching and she doesn’t seem to mind you actually do have a fetish after all. You know full well the time is ripe for a strike. But no matter what, you just can’t bring yourself to do it.

You’re worried you may be misreading her. Trying and failing would set your emotional development back years. It’s safer to keep on talking and looking her in the eye in a way you think is romantic but is actually just plain eerie. You take comfort in the illusion of success. I call it the Shutter Island effect.

The good news: it’s normal. The bad news: you really do have to kiss her to kiss her. The solution: accept the possibility of humiliation as a fact nature, and go ahead anyway. As Neil Strauss, the famous pick-up artist put it: “To get a woman, you have to be willing to risk losing her.”

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Sten Sootla

Building robots by day, thinking hard how not to become one myself by night.