How To Properly Hit On The Waitress

An unpredictable opinion, written by Will Collette

She looked like Taylor Swift.

Not the new edgy Taylor, the innocent one who looked through a window in the
original “You Belong With Me”. Black, thick framed glasses, long curly hair, and a
smile with deep red lip stick. Lawd, Jesus.

This Johnny Rockets waitress was a babe. And I was determined to get her
number. If you’re interested in what kind of date I would have taken her on, check
out the chapter on Tinder in The Art Of Unpredictability.

But you can’t just hit on the waitress. She already deals with that garbage all day
from a thousand other guys like you. Plus, it’s literally her job to be nice to you.
This isn’t the right venue.

But she looked like Taylor Swift. If I walked out on this, it would have been the
biggest ‘L’ since I bet a grand on black at the roulette wheel and lost (true story – 3/10 – wouldn’t

I had to come up with a way to win this girl’s attention, and obviously, her
number. I needed something…Unpredictable.

First off, I told her she looked like Taylor Swift. So we could at least establish that
she was attractive without directly saying it. “You’re hot” is not the opening line to
use on your server, gents.

Polite “yes, ma’am’s” and “no, ma’am’s” helped push me away from the creeps
who come in and order a burger and stare at this waitress from a distance. Now
I’ve established that I was at least a gentleman.

I still couldn’t directly ask her for her number. Especially in front of my friends. So
we came up with a plan:

“I want to take a photo of my friends by the mall fountain,” I told her, “but when
we tried earlier, the security guard got super mad that we stood on the ledge.
Which kind of makes me want to try again. Do you think we’d get in trouble?”
“Probably.” She said, smiling. “But I still think you should do it.”
“You’re right,” I said, signing the check, “we’ll come back with an update.”

I didn’t want to be a jerk to security, so I asked them if we could take the photo
with their permission, this time.
“NO. I’m in the middle of something.” He said, in an aggressive tone.
Alright, Paul Blart. Simmer down.

“Isn’t that a stuffed animal you’re holding?” I said, looking at the little owl in his
“The answer is NO.” He said, storming off.

Apparently, someone left stuffed animals around the mall with notes that said
“take me home.” Either this was serious terrorist activity, or someone had some
unpredictable ways of giving back to the community. Either way, I had to return to
Johnny Rockets empty-handed.

“So the photo didn’t work out,” I told the Johnny Rocket’s Taylor Swift
doppleganger, “security was still upset.”

“Well at least you tried.”

“Yeah,” my blood pressure started to build, “I promised myself I’d do this
challenge where I’d take every chance I could for 21 days. Now, I don’t believe in
asking a waitress for her number while I’m a customer. But since I’m no longer a
customer, can I ask you now?”

She smiled.

“I have a boyfriend.”


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