Does Jake Gyllenhaal know I’m in this room?

Kaitlyn Tiffany
7 min readSep 22, 2018

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 far as I know he never subscribed. He may have used an alias, but odds are low, given the newsletter had 126 readers at peak and most of them were named family members, coworkers, and men I don’t know who reply to my tweets too much. During this time, at the request of an editor at the popular tech website I worked for, I attempted to use my press credentials to interview Jake about his terrible astronaut movie Life, and received an email from his publicist that indicated to me that either 1) both she and Jake had no idea who I was and had become suddenly and indecipherably selective about press opportunities (he has literally done interviews in the last year with websites called “34th Street Magazine” and “The New York Times on Facebook Live”), or 2) at least one of them — and almost definitely her— had every idea who I…

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