Tabloid Flash Fiction: Leonardo DiCaprio and Tobey Maguire Wear the Same Outfit, Again

Can Maguire Recover in Time for Their Double Date?

By Sam Eichner ·

"If you happen to be dating Leonardo DiCaprio (which would mean you're a 7-foot tall Victoria's Secret model), then you have already accepted several nonnegotiable truths before you meet up for a date: he will probably vape, he will probably arrive on a CitiBike, he will use all of this clothes to hide his face from the paparazzi, he might wear a plastic bag just because, and he will not dress up for the occasion. Which is exactly how Leo turned up yesterday to a hang in Soho with model Alina Baikova, an unidentified blond woman, and founding member of DiCaprio & Co.'s P*ssy Posse, Tobey Maquire—who was dressed identically like DiCaprio."

via GQ



“Not again.”

“I thought you were—”


“But you said—”

“Nope. You knew I was wearing this today, Tobey.”

“Sorry, boss.”

theimagedirect.com via GQ

Maguire hangs his head. Leo lifts his chin up and stares at him with those penetrating eyes.

Then he says: “Did you bring the Tic-Tacs?”

Maguire frantically checks his pockets. Finally, he feels something on the sleeve pocket of his bomber jacket. They’re in there. He breathes a sigh of relief, and pulls out a box of wintergreen Tic-Tacs.

“Got ‘em, Leo.”

Leo holds out the palm of his hand and Maguire obsequiously pours a few out. Leo tosses them back.

“So who are the girls?” Maguire asks.

“Alina and her unidentified blonde friend.”

“Cool.” Maguire nods his head. “Cool.”

“Don’t worry,” Leo says, pulling the hood over his baseball cap. “Alina told me her friend thinks you’re cute.”


“Yeah. She loves Seabiscuit. Huge fan.”

The pair walk down the street, Leo leading the way. He puts a toothpick in his mouth. Spying some trash on the street, he stops in his tracks.

“Fucking littering,” he says, shaking his head. He doesn’t make a move to pick it up. Maguire looks at him, then the trash, then back at Leo. Their eyes meet. Maguire bends down to pick up the trash and places it in the bin. The two men continue walking down the streets of Soho.

“Is that my new friend Jonah Hill?” Leo asks, peering down the street. Indeed, Jonah Hill, mankind’s new style savior, is ambling down the block by himself.

“Hey Jonah!” Leo says as Hill approaches. They embrace. Maguire shuffles his feet. “This is my old friend Tobey. You might recognize his voice from Boss Baby?”

“Oh, yeah,” Hill says. “I loved that movie. A baby. Who’s also a boss? Who thinks of that shit?”

“I know, right?” Leo says. Maguire’s face has turned bright red.

“Well, I’ve gotta go nail chill gym style,” Hill says, slapping Leo on the back. “Nice seeing you, man.”

“What a great actor,” Leo says, shaking his head in disbelief at how great an actor and friend and overall person Hill is.

The two continue on down the block until, in the distance, Leo spots Alina smiling and waving and heading towards them. Her friend—tall, blonde, also a model—lags slightly behind.

“Don’t be nervous, Tobey,” Leo says. “We don’t want a repeat of that horrendous double date with Toni and her friend, do we?”

“That was four years ago, Leo,” Maguire says. His palms are sweating. He wants to hide—behind a Spidey suit or, better yet, an animated baby.

Alina and Leo hug and kiss and then Alina steps back to introduce unidentified blonde woman.

“This is my friend, unidentified blonde woman,” she says. “This is Leo and Tobey.”

Tobey and Leo shake unidentified blonde woman’s hand.

“Hey,” she suddenly exclaims. “You guys look like twins!”

Alina and her friend laugh. Leo chuckles along half-heartedly, before shooting a look at Maguire. Under his breath, he whispers: “Next time, I’m fucking bringing Jonah.”

Sam Eichner

Sam Eichner likes literature, reality television and his twin cats equally. He has consistently been told he needs a shave since he started growing facial hair.

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