Credit: Alison Segel

There are several times in my life where I’ve flirted unsuccessfully:

-Age 5, when I put on my mother’s bra and stuffed it with toilet paper in order to impress my then neighbor, 80’s actor Steve Guttenberg.

-6th grade, when I memorized all the lyrics to Coolio’s “Gangsta’s Paradise” and performed them for my crush during recess.

-3-years-ago, when I drank too much at a party and asked my love interest to dance. He gave me water and called me an Uber instead.

Essentially, I’d define my flirting style as “full Josie Grosie.” So much so that last week I found myself looking up “how to flirt” on Google (no judgment please, this is a safe space.) I ended up on a WikiHow page that laid out explicit directions.

For one week, I decided to take advice from this WikiHow article on how to flirt.

I would practice one skill a day, and hopefully, by the end of the week, go from a Josie Grosie to a Jessica Rabbit. (Shh, just go with it.) These are the results of that incredibly scientific experiment.

Day One Advice: Look and Feel Your Best!

This was hard for me right now. I recently bleached my hair Khaleesi white and as a result had so much breakage that my hair resembled a mullet with little baby bangs that differed in length and split at the ends. As Paris Hilton would say, “that’s hot.” But if I’ve learned one thing, it’s this: beauty comes from within, and confidence is everything. Unfortunately, right now I was only confident that I was not looking my best.

should I flirt at this person?
should I flirt at this person?

Day Two Advice: Find good conversation starters!

Here is WikiHow’s suggestion on how to start a conversation with a stranger: “You seem like a math whiz. Can you help me do this algebraic equation?” I wasn’t sure if this was directed at high school students still in math class, if WikiHow wanted me to have a boyfriend who was good at math, or if this would work for anyone. It seemed oddly reminiscent of the one liners pick up artists use. Either way, I was committed to HARD HITTING JOURNALISM and my love life. I gave it a shot.




Maybe not.Day Three Advice: Smile with your eyes.


I did not know that Tyra Banks wrote advice for WikiHow! Listen, your girl (I’m your girl) has been studying smizing ever since I watched my first episode of America’s Next Top Model. I’ve just never done it AT someone before. But you know what they say, eyes are the mouths of the forehead. Since this week was all about trying, it was time to… try.

First, I “smiled with my eyes” towards a hot guy on my street as he walked by. He noticed me 0%.


Next, I decided to smize in the direction of the hot barista I’ve had a crush on for the past few months. He knows my name by heart. Unfortunately, he thinks my name is Jessica, but either way, I think we potentially have something special brewing. This is how it went down.

Me (smizing): Hey! Can I get a large iced coffee?

Him: You betcha. (pause) Is there something wrong?

Me: No. No, why? (still smizing)

Him: I thought you were glaring at me. (laughing) You look furious.

Me: What! Hahahah! (awkward laughter that goes on too long, I look potentially crazy)

Him: Ok bye! Good to see you, Jessica!


My smize looked more like a scowl. Maybe smizing wasn’t for me. No more smizing. Good chat.

Day Four: Use body language and break the touch barrier.

Personal space? Not on my watch! I actually had a coffee date today with a guy I met on an app. Typically, I tend to be a little reserved and closed off. My shyness can read as friend zoning. Day 4 was going to be an interesting experiment.

When we met for coffee, I gave my date a long hug. I lingered a bit too long. When we parted, prolonged eye contact. A deliberate smile.

I echoed my date’s body language. I laughed when he laughed. I smiled when he smiled. When he said something personal, I touched his arm. I played with my hair. I accidentally brushed my foot against his and giggled. It all felt incredibly inauthentic. I was acting. I was putting on a show. I wasn’t present for a second of it.

He asked me out on a second date.

Day Five: Compliment your crush early on in the conversation…BUT don’t come on too strong.


He never responded. I thought by Day 7 I would at least hear something, but no. Maybe starting OFF with a compliment was too aggressive? I didn’t think so. If I throw my phone into the ocean now, will I still be able to finish this article?

Day Six: Make eye contact, wink, bat your eyelashes, or raise your eyebrows at your crush.

Easy enough. I don’t have a crush though. But I’ll practice the techniques, and I’ll practice them EVERYWHERE, with EVERYONE! I had two major activities for the day: a job interview, and my yearly checkup at the gyno.

Here’s what I learned for the day.

Making intense eye contact, winking, and batting your eyelashes while in stirrups at the gynecologist makes for a really uncomfortable experience.


Winking and raising your eyebrows during a job interview makes you seem like you’re a fraud/liar. They don’t like it!

Summary: the eye stuff did not feel flirty.


I’ve decided to make up my own rule. Here it is: following rules off the internet on how to flirt is dumb. Unless I am an X-Men or Kate Upton, I probably can’t squint at someone or ask them questions about math until they like me. So here it is: I think I’m just going to continue being myself. Being real is the best flirting style there is.