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Does Jake Gyllenhaal know I’m in this room?

This is a question I ask myself about 40 times a day, because I guess I just sort of assume that wherever Jake Gyllenhaal is, he’s working hard to figure out what I’m doing. Such is our bond. Such is my belief that I’m young and hot enough to command space in the brain of an A-list celebrity who has rejected Anne Hathaway and Chloë Sevigny in his films.

Just kidding! As I am constantly reminding everyone: I wrote a free weekly newsletter about Jake Gyllenhaal for a full year. And as…


A deli Q&A with Jessica Friedmann, which helped

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On Australian journalist and memoirist Jessica Friedmann’s first-ever day in New York City, she was supposed to meet me in the lobby of the Ace Hotel to do an interview about her essay collection Things That Helped: On Postpartum Depression. I had to email her from the bar to tell her we’d have to improvise, as there were no empty seats. I should have known that would be the case because there are never any empty seats, and in the moments of sending the email and looking around for her, I was…


How social media can turn your infatuation into a one-woman surveillance state

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Photo by DESIGNECOLOGIST on Unsplash

It was late spring in Manhattan. An old, minor Tinder fling replied to one of my tweets while I was sitting on the C train, drinking vodka from a seltzer bottle, heading to a birthday party I didn’t feel like attending.

I hit the tiny heart under the reply and thought, “I’m gonna make him show up later, just to prove that I can.” (I was honestly kind of a dick that year!) And so we kissed for like, 11 seconds in the street after the birthday girl had gone home and after the friend who was crashing at my…


If we lived here, we’d be alright by now

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TLA

It’s Wednesday night in Philadelphia, and the kids clamoring into line in front of the Theatre of Living Arts are the only people on the street. I have a rock made of bread in my stomach. Two girls in crop tops are turned away at the door because, not only are they visibly drunk, they’re also holding open containers and breathing beer into a security guard’s face while he reads the post-Millennium birth dates on their drivers’ licenses.

Tonight is, kind of, a pit stop on Brockhampton’s Love Your Parents tour…

Kaitlyn Tiffany

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