The Southwest Airlines Flirt

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photo by SkilliShots

This new Southwest Airlines service to Chicago has Minnesotans giddy. Instead of wasting another night at the CC desperately hoping for a Josh Hartnett sighting, we can hop down to Wicker Park and hope for a Kanye sighting. It's the small things in life.

Like picking up women on the plane.

A friend recently called with frantic news to inform me of the great Southwest flirt. He flies around the country on Southwest. He also boned a girl in a Vegas handicap bathroom, for what it's worth.

"Dude," he says, "It's perfect if you play it right. You get to pick your seat."

He went on to tell me about the Southwest flirt. For a lonely man new to the airline, it works like this:

Pre-boarding: Southwest has their passengers line-up in a bus style formation. Here is where you can scope the action. If you're lucky, a hottie will be a number or two away. The key thing is not to fret. Pick the top five hottest girls. Rate them. It's okay. You're already using a plane flight as way to meet women, what's another step down the lonesome road of desperation?

Boarding: Now it gets serious. Be sure to board late, but not too late. You want to board the plane just after all the hotties. And if you have an iPhone, take it out; the little wonders work like invisible spray. The ladies won't know what hit them, until you start hitting on them. Something we'll get to later.

Picking a seat: Usually, hot girls sit next to the window. Not sure why, but they do. Here, your tardiness comes in handy, the bitch seat will be open. Take it casually, do a nice nod and take out the emergency landing card. Chicks totally dig guys who read emergency landing cards.

The flight: Pull out the provided magazine. Flip to the end and start filling out the cross words puzzle. No need to be correct with your answers, just be sure to fill in every box. She can't help but notice your skills. If she really stares just mutter, "I got addicted after seeing the Will Shortz documentary." Chicks totally dig Will Shortz.

The flight (continued): Once you reach a cruising altitude, stare out her window. She'll think you're staring at her, then notice you're not, even though you are. Now's the time to drop the bomb. A subtle, "You from Chicago?" works great. Then casually name drop Northwestern, it doesn't matter if you didn't go there, she'll never know. It's a big enough school. If she presses, just say you did j-school at Medill. Chicks totally dig journalists.

Even if all they do is provide nonsense for a living.

But trust us on the Southwest flirt. It's cheap. And the girl is stuck with you.


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