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17 cringe-worthy Chicago pickup lines

Written by
Madeline Wolfson
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Dating has gone mostly digital and we’d like to think we’re moving towards a more respectful, less objectifying mode of making that first connection. Still, there’s always someone eager to lay down a cheesy-as-deep dish pickup line, undeterred by rejection or rolling eyes. Here are 17 Chicago-specific, totally cringe-worthy lines for you to use at your own risk.

You must be why they call this the Windy City, because you’re blowing me away.

Is this seat taken, or has someone else already called dibs?

The trains aren’t the only thing elevated at the moment.

I've had a dry spell longer than the Chicago Cubs—wanna help me make it to the World Series?

Let's eat an entire deep dish pizza and go into a food coma together.

Is that Cloud Gate in your pocket? Because I can see myself in your pants.

Have we danced together at the Owl before?

Let's make like Clark the Cub and watch baseball with our pants off.

Have I seen you at the Art Institute before, or am I remembering a different masterpiece?

You may not be a Divvy bike, but I’ve been checking you out for almost half an hour.

Can I get you another Malort?

Did we travel back to 1871? 'Cuz it feels like we’re on fire.

Are you a state or local politician, because you look scandalous.

Like the Chicago River, I’ve been known to go both ways.

Have I seen you on Empire?

Turns out I didn’t need to go up to the top of the Sears Tower to get the best view in Chicago.

I know you just toured the Robie house, but how would you like check out another Wright house? Mr. Right.

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