Anatomy of a Failed Pick-Up

On weekends, I live a second life as a hostess at a chain restaurant in downtown Chicago. Overall, I like to describe the experience as “humbling.” And sometimes- on a rare occasion- I get a phone number.

Hi Charlie.

Enter Charlie.

(Disclaimer: Charlie was drunk. This particular level of suaveness can only be achieved after a certain point of intoxication.)

The following steps explain how to not get a lady:

Step 1: Over-complimenting

Contrary to popular opinion, there is such a thing as being too… whatever you call this. Throwing down amazing amounts of “beautiful, gorgeous, pretty, sexy” isn’t going to do anything for you, other than leading you to be categorized as “sketchy” or “creeper.” Certain things are only beneficial when they’re sincere. Disingenuous complimenting will get you nowhere.

Also, there’s absolutely no way to look sexy in that work uniform. Have you guys seen slip resistant shoes? Yeah.

Step 2: Living across the country

There’s nothing like admitting you live in LA to a girl in Chicago.

Step 3: “Sweetie”-ing

Never acceptable. Unless you are my grandfather.

Step 4: Impressive levels of forwardness

While telling me that upon admiring my existence at the host stand, you came to the conclusion that you wanted to kiss me is one thing, blatantly telling me you want me without ever having an actual conversation with me is super special. Meaning not okay.

Step 5: Then followed by asking her what her interests are

You can’t tell me you want to have sex with me and then ask me what my interests are. We’re way past trying to get to know each other, sir.

Step 6: “Am I a women’s issue?”


Step 7: Making assumptions based on major/college

I made the mistake of assuming everyone in Chicago knows that Columbia means Columbia College Chicago and not the super prestigious Columbia University in New York. I told Charlie I was studying journalism and he told me all about liking smart girls. When I corrected him about my school, he did the whole well, then, I’m into artsy girls, too. Listen up. Stereotypes are never cool, but seriously, don’t insult a lady’s intelligence.

Step 8: “Did I give you enough material?”



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