times I thought I was flirting man repeller
5 Times I *Thought* I Was Flirting
07.19.19

My flirting abilities peaked in middle school. It was easy, at 13, to flirt from behind the safety of a computer screen, since all of my romantic relationships took root in the rich soil of an AIM chatroom. While I stumbled and stuttered the first time I told a boy “I like you” to his face, on AIM I gained a reputation as a certified heartbreaker. It was there that I got my first boyfriend, Adam W, whom I promptly dumped for my second boyfriend, Ryan.

Chatting with Ryan via heart emoticons was easy, but the prospect of meeting in person sent a shiver down my spine. Eventually, though, there was no other choice; we would be meeting, at his request, under the bleachers at a high school football game. The first words I spoke to Ryan were uttered under those bleachers, where I extended the small talk for as long as I could bear before we decided to kiss. Ryan told me I tasted like chapstick. I told him I appreciated the compliment. We broke up shortly after, and I soon entered high school only to discover I was not quite as adept at flirting in the real world as I had thought.

In fact, as time has gone on, I’ve come to believe the radar that others use to figure out when someone is flirting with them is broken in me, if not completely absent. Because many times I have thought I was flirting, and many times I have been wrong. Here, dear reader, are five of those times, explained.

That Time I Needed Assistance at Williams Sonoma

An old boss once asked me to help her with a photoshoot. Because my job at that time was to “bring personality” to the social media pages of various cleaning products, I salivated at the idea of escaping the trenches of Twitter to be “on set.” I was filled with visions of flashing lights, brushing hair off of models’ cheeks, and a large snack spread. I was not filled with visions of hefting slabs of marble that she had bought from Williams Sonoma across town. And yet, when my boss handed me a list of “photoshoot errands,” that task was at the top.

The problem was, when I got to Williams Sonoma, I could not lift even one slab of marble, a realization that brought me to tears and confirmed my trainer’s accusations of a weak core. Tragic heroine that I was, a man swooped in and offered to help me carry the slabs back to the office. It became immediately clear that this man was in love with me, but it wasn’t until we were almost back at my office that he offered to have me over for dinner. I smiled. I said yes. I was no longer crying. “Great,” he responded, “my husband loves to cook.”

That Time I Fell in Love on the Subway

Once my roommate got a boy’s number on the subway. A stranger had been flirting with her, incessantly asking for her number, and another stranger came to her rescue—walked up to the two of them talking and claimed to be her boyfriend, just like something out of a movie. I was, of course, envious of her meet cute; I wanted my own subway romance.

I decided to start with suggestive eye contact. During my first attempt, I trained my gaze upon a young man across from me. My eye contact, I was surprised to find, was returned. Staring into each other’s eyes, I felt that the chemistry was so palpable I remember being vaguely worried for the poor souls trapped in our Love Boat (subway car). He broke the silence first. As his mouth opened, I was already prepared to give him my number, my love, my everything.

“What’re you staring at?” he asked me, in a tone that I was dismayed to note was aggressive.

“You,” I whispered back, hoping we could turn things around.

“You’re just a poor little rich girl,” he replied, before taking his leave.

I’m still not sure what he meant, and I still maintain that it’s possible we were flirting, though my friends insist on telling me otherwise.

The Time Sebastian Trained Me

I once hired a one-time personal training session with a man named Sebastian, and soon learned I have trouble interpreting the kind of touching training involves as professional. So when, after an hour of sweaty banter, Sebastian told me to “hit the showers,” it sounded quite suggestive. In retrospect, I may have just smelled. And later, when he slid a pamphlet of pricing options across the table towards me, I realized his kindness was more likely a marketing ploy than a courting exercise. That said, I still see him at the gym from time to time, so I’m open to any signals that suggest otherwise.

That Time I Met a Haim Doppelganger

I’ve left my number for many men and women over the course of my life. Most often I’ll leave it on the back of a receipt at a restaurant or bar, along with a note for them to “Call me!” written in my most legible handwriting. It’s the coward’s way of flirting, I’ll confess, a sort of throwback to my beloved AIM chatroom days. But I like it: If they decide not to call, if they have a girlfriend or a boyfriend, I never have to know. (Although I tell myself they simply lost the receipt and then realize I can never go back to that restaurant again.)

Recently, a bartender was tasked with serving my friends and I. She looked like the most beautiful member of Haim, so I, of course, decided to tell her so. “You look like the most beautiful member of Haim,” I said, and started pulling up photos on my phone. She responded by bringing over three free shots of tequila on the house. I took this as a sign and decided to leave her my number. But in a bout of unfortunate timing, she came to grab the check before I left and saw my note. She smiled at me and said, “I’m not…” and I realized with dawning disappointment that this was simply one more bar to which I would never return.

That Time I Tried to Woo My Pharmacist

Every time I go to the pharmacy, I feel like I’m assisted either by a wildly attractive pharmacist or someone of barely legal drinking age. Nothing like asking the 14-year-old behind the counter for your Plan B to make sure you stay grounded. But with the more attractive (and age-appropriate) alternative, I maintain that flirting with my pharmacist is almost always possible, even when that pharmacist is handing me my prescription-strength Monistat.

According to my mother, I have always had a “weak stomach,” which means I am a frequent patron of my local pharmacy. Upon returning from a recent trip to Costa Rica, I made a trip to the pharmacy to pick up some prescriptions and, on my way through the store, grabbed a few handfuls of Imodium. I placed my goods on the counter, only to look into the eyes of a man who, I am convinced, has a second job as a model. He asked for my name (a good sign). He started listing off my medications while I nodded in an attempt to appear breezy (a hard vibe to pull off whilst calculating how long I could last before I needed access to the nearest bathroom).

When he asked if I needed anything else, I replied, “Just my usual,” expecting a laugh that did not come. This, I will admit, was a less good sign. He asked me to confirm my address, my phone number. “That’s my number, all right!” I replied with, I’ll admit it, a wink. After he bagged my prescriptions and handed them to me, I attempted a sexy waltz out of the store on the off chance he was watching. He never called. But of course, my beautiful pharmacist would never commit such a breach of privacy.


I may look back with nostalgia on the days of AIM and away messages, but in today’s world of Tinder and Bumble, I’ve found that it’s still possible to flirt sans verbal communication, so I remain hopeful. I’ve got a classic opening line, a profile picture in which I’m wearing a beret, a bio that explains my cat allergy. For all the perils of the apps, I can at least find solace in one certainty: We are flirting.

Gif by Emily Zirimis.

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