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Illustration: Kim Rosen

Test-driving pick-up lines

Two single writers try out their best pick-up lines.



“I’m not straight,” [a lie] “but there’s just something about you that’s so intriguing.”
I nervously approach my target at Logan Bar & Grill (2230 N California Ave, 773-252-1110): mid-thirties, clean cut. When I deliver the line, I get a bewildered, “Really? Why?” As I muster a response, a woman appears from the fringe like a lioness protecting her cub. I failed to notice his wedding ring.

Sean, 35, says he was flattered a lesbian (he believed me) would think he’s intriguing, but he had no idea I was hitting on him. He adds that while it was a great conversation hook, were he single he’d assume it would go nowhere. “She’s never gonna switch teams.”

“Why don’t you join us?”
When I spy a tall, curly-haired cutie at the Charleston (2076 N Hoyne Ave, 773-489-4757), I ask if he’d like to sit down with me and my wing-women. He smiles and says “maybe.” I say, “I think you should, sooner rather than later.” He nods amicably but returns to his friends.

When I ask how I performed, Joe, 30, says my line didn’t feel specific. “Plus, there was no extra seat.” (Whoops.) He figured we had made contact and would know where to find each other. What could I have done differently? His answer: Go to the bar, alone, smile and make eye contact. “That’s the green light,” he says.

“What’s up with the beard?”
I’m drinking with a friend near the door of Rainbo Club (1150 N Damen Ave, 773-489-5999) when a tall, scruffy guy walks in. After I throw out my facial-hair line, we start talking, and his friend, also cute, joins in. Soon, there’s an easy banter among the four of us.

Alex, 26, tells me it was a great pickup line. “You appealed to my sense of vanity.” I ask if ladies approach him a lot and he unabashedly says yes. “I’m kind of lazy. I appreciate being hit on and I don’t necessarily conform to mores on dating.”—Erin Ensign


“Are you Jamaican? Cuz you’re Jamaican me crazy.”
Losing track of how much liquid courage (read: cheap bourbon) I’ve consumed at Four Moon (1847 W Roscoe St, 773-929-6666), I slide over to a blond, athletic-looking 24-year-old named Cindy. She looks disconnected sitting at a table of giggly GFs. Maybe my cheeseball line will break her out of the apparent funk.

Nope. “That’s fucking awful,” she replies, disgusted. Her advice: “Recite a random fact that you learned that day—something geeky but adorable to break the ice.”

An eavesdropping bro butts in: “When’s the last time you had that bean smacked?”

That bean?!” Cindy screeches.

“See? Now you’ve got her attention.”

“I feel like Richard Gere right now. I’m standing next to the pretty woman.”
I’m at Underbar (3243 N Western Ave, 773-404-9363), convinced I just hit on the last person on Earth who hasn’t seen Julia Roberts play a hooker. But then 23-year-old Ellen Page look-alike Lauren lets out a delayed but flattered giggle. “It was a really cute surprise,” she says.

Despite the praise, Lauren advises that women prefer less gimmicky game: “Compliment her eyes! It’s like you’re looking directly into her soul.”

Lauren’s friend adds her own seduction story: “A guy got down on one knee and asked me out to pancakes.” Genius.

“I agree with Prince: You don’t have to be rich to be my girl.”
Prince’s “Kiss” bubbles out of the speakers at Nick’s Beer Garden (1516 N Milwaukee Ave, 773-252-1155), when I spot Brittany, a leather-jacketed fox in her late twenties. Suddenly, I feel inhabited by the Purple One’s silky-smooth spirit.

“If you were Prince,” she responds, “I’d go home with you.”

“But I’m not Prince,” I say.

“I know you’re not. That’s the point.” Ouch.

That’s what I get for trying to ride the coattails of the original Sexy MF.—Jake Malooley

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