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Our Date with Drake in N.Y.C.

What Is It: A group date with a cardboard cutout of Drake – a.k.a. Aubrey Graham, a.k.a. America’s Sweetheart – in New York City

Who Tried It: Maria Yagoda and Grace Gavilanes (Features Writers-Reporters)

Level of Difficulty: 2/10 (Only because someone legit tried to pick a fight with the cutout, which was traumatizing for all.)

Part One: Pre-Date Butterflies

Maria: Since the moment we met, my colleague Grace and I have fantasized about taking a life-size cardboard cutout of Drake on a date. (That’s right. Even our wildest fantasy involves a toned-down cardboard version of him, because the idea of kicking it with IRL Drake is so, so, so hopelessly elusive.) As is true of all magnificent ideas, the origin story is murky, but grew from our mutual love for Aubrey Graham and our lifelong dream: spending a romantic evening with him, complete with snacks, photo ops, activities, pointing and laughter (i.e. the sort of activities you set to jovial montage music). After Drake, dressed in a tux, arrived in the mail, we spent two weeks working with him watching over us in the office as we planned the big night, growing evermore alienated from colleagues who were A) creeped out by the fact that cardboard Drake managed to make eye contact with them wherever they were in the office B) small-minded C) jealous.

When the day finally arrived – just a few days before his October 24 birthday – I caked my face in powder and lipstick and tried on several different outfits, opting for something casual: curve-hugging jeans and a cropped sweater. Grace and our other Drake #sisterwife, Julia Emmanuele, left work early to get to the very important work of sweeping Drizzy off his feet. (Literally. Because cardboard cutouts can’t walk. The technology just isn’t there yet.)

Part Two: Duane Reade Run

Grace: You’re about to judge me, but just like that adorable 4-year-old girl who had a CVS-themed birthday party, I, too, am fascinated with pharmacies. The cheap chocolate! The fluorescent lights! The lipstick on clearance! What is there not to like? (Answer: Nothing. Pharmacies are flawless.) So, it only felt right to take our cardboard husband (spoiler alert: He proposed to the three of us at the end at our date – turns out we’re that charming) to the mecca of all things amazing. As soon as we stepped off the escalators and made our way to the makeup aisle, we were instantly greeted by three staffers who were just as infatuated with Drake as we are. Selfies were taken, breakup texts were sent to boyfriends and touch-ups were given. (Unlike us common folk, Drake is never caught with a shiny nose or forehead.)

Part Three: Tim Hortons

Maria: Before really diving into the date, we wanted to show Drake that we both cared about and respected his Canadian heritage. (Also, no first date is complete without an inaugural cream-filled doughnut to set the mood.)

Part Four: Times Square

Grace: I think I can speak for Maria and Julia when I say that our trip to Times Square proved to us how compassionate and non-confrontational Drake really is. We visited the ever-congested Olive Garden, took pictures with a giant Hello Kitty (his idea, not ours) and definitely, maybe, kind of attended a Broadway show. It would have been picture-perfect if it weren’t for Drake’s enviable frame/cult status. We should have known! What was supposed to be an intimate first date turned into instant chaos after a heckler flicked Drake’s neck and a passerby commented about his one-dimensional frame (“he looks thinner than he does on stage” – he’s insecure, okay?). It took everything in us not to break out in the best moves (read: all) from “Hotline Bling” to signal off a dance battle right then and there. That would be downright humiliating for them. Drake’s response to the insults? “What happened between us that night? It always seems to trouble me.” And he let it go.

Part Five: Bryant Park

Maria: The sun was setting. A glow hovered over the park, a quietness. I was struck by this horrific, sinking feeling that I may never hang out with Drake again. We all sat down at a table, and I rummaged some more Tim Hortons out of my bag, for us all to share. Grace pulled out some grapes she had. We were mostly silent, but happy. I mean, we had just done the damn thing. We had spent an evening with a cardboard version of the most dapper guy in the world.

At the end of the night, I wanted some alone time with him, so I took him to the park’s fountain. I grabbed some moist (how?), crumb-covered (how?) pennies from the bottom of my purse and made a wish: Let this night last forever. I threw the coins over my shoulder into the fountain. (Sorry, parks department, for polluting your fountains.) Tragically, my wish didn’t come true – the night had ended. Probably because I’m telling you the wish now. You’re never supposed to reveal the wish.

Anyhow, we brought cardboard Drake back to the office, where he will rest until we have the courage to ask him out again.

Part Six: What We Learned

Maria: Follow your dreams.
Grace: I feel invincible. Like a mothaf—–‘ legend.

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Reinaldo Massengill

Update: 2024-09-18