Flirting my way through Cuffing Season

A report from my month-long attempt to talk to men in the wild

In October, I had dinner with a few friends and we somehow got around to the topic of cuffing season. The next day someone shared this meme in the group chat, whereupon we all realized that we were wildly behind schedule:

Who starts “scouting” for cuffing season in August?? Also, who are these people who can find enough prospects to date so that by September they’re picking their TOP candidates?? Most people I know have a hard time meeting one person normal enough to get an overpriced coffee with on a weekend morning, let alone multiple.

I have never succeeded at securing a boyfriend during cuffing season. I’ve never been a first-round pick, a second-string alternate, or even considered for the draft, to use some sports analogies with only a vague understanding of what they mean.

Despite being very out-of-shape in the dating department, I decided to gear up for the winter ahead. For the entire month of November, I set a personal goal to flirt with five men a week. No, not from the comfort of my iPhone by using a dating app: I was going to venture out and flirt with men in person, or “in the wild”, as the youths now call it.

Formulating a flirting game plan

Scouting officially began while out on Halloween, when I met a hot guy dressed in a black trash bag who told me he was a raisin and that he worked as a sous chef at a fine dining restaurant, thus fulfilling every sexual fantasy I’ve ever had about Mr. Yes, Chef himself. Unfortunately, I did not get his number because he left the bar to go to another party and said he would come back, but in a plot twist everyone reading this will see coming, he did not and I went home.

Most of my flirting attempts occurred at coffee shops, because that’s where I spend most of my time as an unemployed person contributing to society by helping baristas pay their rent. During the first week of the flirting challenge, I smiled at a cute guy sitting across from me. He looked up and gave me a warm smile in return. Was it true love?!?!?!? I wondered. Is it really this easy?!

He was sitting slightly too far away for me to say hi, so I texted a friend to formulate a game plan. This was her response:

I did not Airdrop him a nude, but I was learning that approaching attractive people in public takes a certain amount of finesse. Or when in doubt, politely ask if they wouldn’t mind moving their laptop bag so you can sit next to them, and maybe flash a little cleavage while you check your email.

Let the awkwardness ensue

When you try to talk to men in public, you learn two things: 1. the nicest, friendliest men are married, and 2. the cutest ones are usually gay. There were times when I felt bad after striking up a conversation with a guy and then saw that he was wearing a wedding ring on his left hand, while he continued to tell me about the book he was reading that his WIFE’s book club had selected. I nodded enthusiastically as he described the entire plot of said book, wishing I could interrupt and just say, oh sorry, dude, I was only talking to you because I’m a lonely single woman trying to find a husband of my own: a guy like you who is down to join my book club and read The Seven Husbands of Evelyn Hugo, not because you’re a big Taylor Jenkins Reid fan, but because you love the crap out of me and would do anything to keep the spark alive (is there any hot sex in this book? Where does it fall on the heat scale?) I would ask you but you’re married and don’t want you to think that I’m flirting with you, which was my original intention from the start, but let me back out of this conversation as awkwardly as possible.

By week three, I thought I’d hit my stride when I met a guy at a networking event who was very flirty with me—not the other way around. I also got this close to going to a screening of “American Psycho” (the perfect first date film, right?) with a guy who works behind the counter at a neighborhood food truck, but the movie was sold out.

Last weekend, a few lady friends and I decided to go out to the bars and try to meet men. Were we successful? Absolutely not. Did three-fifths of the lady gang spend the entire night on their phones, not looking or talking to a single man? Absolutely yes. Did one of my friends bravely walk up to a guy who looked exactly like Timothee Chalamet and ask him what’s next after his recent appearance on SNL? Actually yes—and he played along by doing a perfect Timmy impression. But we all still went home alone to our queen-sized beds, weighted blankets, and emotional support animals that serve as a substitute for a real human to cuddle with.

Keeping score while not scoring

Here’s a breakdown of my flirting stats, to use some more vague sports terms:

Week One: 2/5 flirts
Week Two: 3/5 flirts
Week Three: 5/5 flirts
Week Four (Thanksgiving): 2/5 flirts
Week Five: 5/5 flirts

Total number of men flirted with in the wild: 17
Total number of men who flirted with me: 2
Phone numbers exchanged: 3
Number of flirty texts received or sent: 0
Number of dates this month: 0
Number of hookups that resulted from my flirting efforts: 0
Number of times I felt completely hopeless about my love life and was convinced I will die alone: 1,895

So, as you can probably tell, after a full month of “scouting” for cuffing season, I failed to secure any prospects to keep me warm this winter. I was not crowned the MVP of flirting. This late in the season, I would have to make an incredible comeback worthy of an ESPN “30 for 30” documentary to make it to the championship game. On a more positive note, I now have an entire roster of married men who would just love to be my friend and hang out platonically.