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The Time I Almost Married Jake Gyllenhaal

When destiny calls.

By Morgan LongfordPublished 3 months ago 9 min read
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The Time I Almost Married Jake Gyllenhaal
Photo by Ben Rosett on Unsplash

‘Twas Winter, in the year of our Lord 2011 (roughly,) when I almost married Jake Gyllenhaal.

Jake Gyllenhaal has been a celebrity crush since the Donnie Darko days, picking up steam in the Bubble Boy era, and gradually growing stronger and stronger. You may think adult women don’t get celebrity crushes, but you’d be wrong. We do. Sometimes, they are childhood crushes that have followed us into adulthood, and sometimes it is a new, budding imaginary romance in middle age, but I don’t know that we ever move past them. So anyhoo. Jake Gyllenhaal.

I moved to Austin, Texas in 2009. I was working at Whole Foods at the downtown Austin location (only one of two in Austin at the time, not that it’s relevant, although maybe it is. Who knows. But felt worth the mention.) I worked in the Bakery department, which meant that some days you would work the cake counter, some days, the bread counter, and somedays, you would be stranded by your lonesome over on what we called “Candy Island.” It is long enough ago now to say with confidence, I have no idea if that is what customers knew it as. I also haven’t been in that store for years, so I don’t even know if it is a thing anymore, or if it has been remodeled into something else. But for us, I think most of the Bakery team dreaded Candy Island shifts, unless you worked a mid-shift. And even then, it was awful for reasons I will soon discuss. In addition, it was tedious, and yet boring, and it was pretty solitary because you were mostly alone, which I would probably long for these days, but as a brand-new person to Austin, with no friends, Candy Island was a sad little place.

The morning shift at candy island meant setting up tiny little rows of truffles, barks, and toffees, assembling and preparing the chocolate on the gas stove for the dreaded chocolate fountain. The closing shift had to do it all in reverse, but cleaning the chocolate fountain took forever- using a spatula to get as much of the liquified chocolate off the different tiers and center spiral into a giant bowl, trying not to leave any behind but also trying not to spill (because it was a pain in the ass to clean) and was messy as hell. But what may have been the worst- aside from having to wear the ugly, ill-fitting chef’s coats (and if you worked a mid-shift, all the good sizes were gone, so my 110-pound frame would just be swimming in a XXL like a child playing dress up in their parents’ clothes, floppy arms and all- never felt sexier let me tell you,) was the way people would gather around the tall glass and watch you fill the cannoli shells from the fountain, or dip the strawberries.

At first, I felt like a bit of a celebrity, putting on a performance of grandeur, delicately dipping each strawberry just right, making it look like living art, an installation, woman and food, courageous, brave, INNOVATIVE. I am here to tell you, that wears off pretty quickly, and then you just feel like a circus monkey doing tricks for the spectators. The way people would press their faces and their grimy ass hands all over the glass to get a closer look like I was part of a traveling side-show, but no one was throwing dollars at me to perform. I don’t blame the people- I’m sure it was mesmerizing to watch, and getting a perfectly filled cannoli is, in fact, an art form. Not to mention, Whole Foods was listed as a local tourist attraction at the time, so people came expecting to be impressed and entertained, and whoever was at Candy Island was the main act. (Sidenote: not only was it a tourist attraction, a must-see Austin landmark, but it was also a hotspot for date nights, which I found insanely bizarre, but alas.) Lastly, Whole Foods Lamar was the go-to spot for celebrity sightings. And this is where Jake comes in to play.

Once chilly winter day, I was working at Candy Island, precariously stacking truffles and dipping berries. I popped my head up from the candy case to check for customers, and There. He. Was. Jake Gyllenhaal in the flesh, not ten feet from me, pushing a shopping cart like he was just some normal guy and not, in fact, Jake Gyllenhaal. I did a double take - it couldn’t be, could it? AND THEN I IMMEDIATLEY LOOKED AWAY. My eyes could not handle the beauty of this man. My SOUL could not handle the beauty of this man. But this was Jake Gyllenhaal, I couldn’t NOT look. I steadied myself, steeled my composure and turned around, to take in the glory that was him.

He was tall. Impeccable posture. Impossibly beautiful. Like. More so than onscreen with all the proper lighting and makeup and everything, and I don’t even know the physics of that. He was wearing a chestnut brown coat, that if I remember correctly, was corduroy and struck me as vintage. This was it. My moment. Of all the celebrities to cross my path, it was the one I daydreamed of for years, the lion king, ruling over the land of Morgan. I prepared myself for our future, imagining that he would come to my counter, order a salted caramel or earl gray truffle, something classy, and when our eyes met, the world would stop spinning for us both right then and there. Love at first sight. Amore on Candy Island. And then, the horror when I remembered I was wearing an impossibly large chef coat, stupid non-slip Shoes for Crews and a Whole Foods hat of some sort. HOW CAN I WOO JAKE GYLLENHAAL WHEN I LOOK LIKE A TODDLER IN MY DAD’S CLOTHES? Instead of fireworks, the embers just blew away in the wind, gray and ashy, taking all the possibility of a life of Hollywood glam and private jets and paparazzi with it. I could’ve died.

Which is fine. I suppose. He never came to the counter anyway, because of course not. Do people like him even buy chocolate? Do they stay away from sugar and carbs and processed meats so they can walk the earth like Adonis? I was spared the humiliation, saved from imminent mortification only to remain a peasant. Or was I? When I got off of work that afternoon and texted my best friend, she told me I had to find him, and that it was “my destiny.” I couldn’t argue with her. Per the tabloids, he had recently gone through a breakup (with the ever-lovely Taylor Swift, and this didn’t complicate things for me then as it would now,) and I could be the one to mend his heart and make him feel complete. The rebound was really the reason- they had to break up so that we could be together. Kismet. So, my best friend and I devised a plan.

We looked at all the top hotels in the area, deciding which would be the most likely place for a celebrity on the go. We decided that Jake would be more of a lowkey vibe kind of guy, not as flashy, and drawn towards local joints versus chain hotels, no matter the caliber. From there, we looked at what bars or music venues would be close by, for nightlife with anonymity. Together, we decided that for sure, he would be staying at the Hotel San Jose- a boutique hotel on Austin’s famous South Congress Avenue- and that he would be at the famous Continental Club that night to take in some live music in a dimly lit bar, where he could go unnoticed under the light of a neon moon. From there, I would go downtown, saddle up to the bar of the Continental Club, where obviously Jake would be sitting solo, and strike up a casual conversation. And this time, I was prepared with a smashing outfit, makeup and hair done, and not a Shoe for Crew in sight.

I was ready to shine, to meet my future husband, and live a life of luxury and leisure as the mysterious, non-celebrity woman that stole his heart. The only problem that arose was that when I got there, there was a cover charge, and I was broke AF. I barely had enough money for a drink once inside, let alone pay to get in. I texted my best friend, let her know that I couldn’t get in and our efforts were all in vain. And then she did what any reasonable best friend would do and told me she would send me a check to reimburse me, (Venmo didn’t exist yet,) that I had to get inside, and money couldn’t keep me from my destiny that was Jake Gyllenhaal. So, I used whatever cash I had to get in, and probably put my drink on a credit card, which is how I paid for just about everything those days because my $400 checks barely covered rent, let alone anything else, and sat at the bar waiting for the man that would make me a Mrs. To arrive.

He never did. To this day, I can’t explain it. I was certain that my best friend and I had chosen correctly, that the plan wasn’t a plan as much as it was divine guidance and intervention. But Jake wasn’t there. Not even the internet could offer any sightings or insight into his whereabouts! I assume he was in town for a few days- hence the grocery shopping- but he was never to be seen by these eyes ever again. Not in person, at least. Maybe I should have made an excuse to talk to him, ask if he needed help finding arugula or something. Maybe I should have broken the ice with jokes about oversized uniforms or offered him a chocolate. I could have reminded him he didn’t get out of that plastic bubble to play it safe, Vato. I should have reminded myself that I didn’t get out of that plastic bubble to play it safe! I suppose it’s for the best. I have a really good life now. I have a wonderful family. My children’s book, Annie the Adventurer, could very well be the best-selling children’s book of all time and I will create my own first-class lifestyle, and live a life of luxury that I designed. And don’t have to deal with the “paps” all the time. But maybe, if I had done any one thing different, I would be writing about my wedding to Jake Gyllenhaal instead of how I almost married him.

pop culturemarriagelovehumorcelebritiesbreakups
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Morgan Longford

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