What I Learned From A Week Of Trying To Pick Up Boys On The Train
I’m an awkward girl who went for it.
Ever since I moved to Chicago, I’ve been falling in love with attractive men on public transit. For 60 minutes a day, I’m within inches of hunky dudes of all shapes and sizes—so close I could touch them (and sometimes I do, because have you ever been in a packed train car?).
Suddenly, it hit me: Why was I not seizing this opportunity to meet someone special?
It’s like passing the same shop every day and eyeing that really cute dress that would be perfect for your BFF’s engagement party, except instead it’s a really cute boy who would look equally as cute on you at your BFF’s engagement party. You stare it down every day and contemplate making moves, until one day you’re like, “screw it, what do I have to lose?” (Besides money or pride, but I digress).
And so, for about a week, I put down my book, turned off my Beyoncé and struck up a conversation (or at least tried) with the beautiful boys of Chicago public transit.
I am an awkward person, the type that says sorry to inanimate objects in my apartment. So naturally, I was worried I was going to make a fool of myself. To overcome my fear, I told myself two things:
1. I will never see the majority of these people again, and the ones I do will hopefully become my husband.
2. I’m basically giving free entertainment for everyone’s otherwise miserable commute, so why not really ham it up and put on a show?
My first victim was basically a young Danny Zuko, and I was all about being his Sandy.
Plus, I was wearing tight black pants and the Blue Line was coated in grease. I crammed into that car and hoped to find some “Summer Lovin’” at 7:45am on a Monday.
This was my first shot at love, and it was the most awkward of them all. I was nervous. My knees were weak, palms were sweaty. It smelled like vomit on the Blue Line already. Okay, enough Eminem. I’m just avoiding sharing this humiliating moment.
I weaseled my way next to him and “soft smiled,” which involves no teeth and a lot of chin tucking. He looked down at me and then immediately above my head.
“It’s so crowded this morning, haha,” I said. Real smooth.
He made a pained noise that sounded a lot like a baby seal dying, then turned the complete opposite direction. Ouch. I put my headphones in and pretended I wasn’t utterly humiliated, regretting my entire existence. My bruised ego and I spent the rest of the commute in silence. I’d suffered my first wound on the battlefield but felt determined to conquer the next day.
My second victim was half reading, half sleeping and had my whole heart.
He was doing two of my favorite things AT THE SAME TIME. It was fate. I recognized the book he was reading and tried to act coy.
On the inside, though, I was already planning our literary-themed wedding. Think of the vintage library card Save The Dates! When the seat next to him opened up, I pounced like a TMZ reporter on a Kardashian. It was just after 6pm, I was wearing my best jean jacket and boy did I feel alive.
I had so much left to say, like, “what did you think of the plot twist in chapter four, ” and, “will you marry me?”
I had to act quick since the blonde-headed reader could get off at any stop. I looked directly into his Warby Parker glasses and smiled, this time making sure my chin was in a better position so I didn’t pull another soft smile. Holy spectacles, he was way cuter up close.
“’The Art of Fielding’ is one of my favorite books,” I said. My voice didn’t even crack. I felt good about this.
“I’m really enjoying it so far,” he said. His voice was soft yet strong, like a Brawny paper towel.
And then, in a cruel twist of fate, the car doors opened at the Division stop and he closed his book, stood up and walked out of my life. This must have been what Gatsby felt like when he first saw Daisy. I had so much left to say, like, “what did you think of the plot twist in chapter four, ” and, “will you marry me?”
My third pursuit was my very own Charlie from “Girls.”
This was season 5 Charlie, so he was real manly. The curly hair, the jean jacket, the beard—all of it reminded me of my HBO crush.
I was wearing a dress, though not nearly as swanky and revealing as Marnie’s, and I was ready for a “The Panic In Central Park” moment. I unsteadily approached Charlie when the bus came to an abrupt halt and I lurched forward. He looked at me and grinned. My dopamine levels spiked straight to my underwear.
“Haha, that was close.” The nervous laughter was kind of getting out of hand at this point. He smiled (again!) and said, “Careful, there.”
Wow. It was a panty-dropping combo of Season 1 Charlie’s kindness with season 5 Charlie’s hotness. We spoke for a few moments longer, and as we approached my stop I decided to just go for it.
“We should get coffee sometime,” I said. “I would love your number.”
“I’m actually on my way to meet my girlfriend for coffee right now,” he replied.
I was devastated. Red-faced, a Charlie Brown cloud formed above my head I and sulked off the bus. I was bummed my “Girls” crush look-a-like slipped between my fingers, but proud of myself for popping the question.
I completely struck out for the rest of the week. Not for lack of trying (I even chased a dark haired babe from one end of the train car to the other) but most of the men I tried to approach were glued to their phones, oblivious to my advances.
Here I was, a real life girl, trying to talk to real life boys and couldn’t, because they were too busy chatting up women on the Internet.
And the most ironic, maddening part was what they were doing on their phones. After a quick, subtle peek at their screens, I saw them cruising Bumble, Tinder, Hinge, etc., trying to find exactly what I was trying to find at that very moment.
Here I was, a real life girl, trying to talk to real life boys and couldn’t, because they were too busy chatting up women on the Internet. I’m not saying I’m a better catch than anyone you might find on dating apps, but I am a person and not a photo on a phone screen.
What I learned from a week of trying to pick up boys on the Blue Line:
I realized that doing something that embarrasses the shit out of you can actually be pretty fucking liberating. Though I didn’t find a Blue Line babe to call my boyfriend, I did find the courage to strike up conversations with strangers—a scarce skill in the age of Tinder.
So beware, men of Chicago public transit. If I think you’re cute, I’m probably going to approach you. I might soft smile or comment on your backpack. Whatever it is, I have nothing to lose.
So get off your phones and look up so I can awkwardly talk to you. There’s no app for that.