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Jessie wore her hat to school, from school, and when she was alone at night. It was a simple enough hat, in many ways. It was gray, with flinty black specks stuck in the felt. The inside was lined with black satin, and it would slide around on her blond hair whenever she walked too fast. Jessie loved that hat more than she loved her dolls, her blanket, and her best friend Leslie. But that was only because Leslie liked to poke kittens with sticks, and hit Jessie when she felt like it.
To Jessie, an entire world lay inside that simple, gray hat. She only had one friend, and she didn’t like her much, but the hat showed her an entire new world of friends. They were strange creatures, her new friends. Some were very tall and very thin. They reminded Jessie a bit like the weeping willow trees in her neighborhood. They had dark brown eyes that sparkled with tears, and their fingers were so long they could reach across the creek that Jessie played at. Some of her other friends were short, but crystalline. They had bright, mischievous blue eyes and they liked to dance. A few only had one eye, while others had eighty.
Jessie’s parents worried very much about their only daughter. They thought that she spent too much time alone, but they didn’t do anything to correct it. Jessie’s mom worked, and Jessie’s dad worked, and so Jessie spent most of her time with the babysitter. Her babysitter’s name was Ashley. Jessie thought she looked a bit like her mom’s frumpy coat. Ashley had a great, round face with fleshy cheeks that were unevenly stained red. Her body was lumpy and misshapen, and she tended to wear clothes that showed off her belly button, which often had lint in it. Jessie didn’t like how Ashley looked, but she didn’t like how Ashley acted, either. Ashley didn’t even pretend to like Jessie. As soon as she arrived at the house each day, she’d make Jessie do her adding and subtracting, and then she’d be sent to her room while Ashley raided the refrigerator and watched “Friends” reruns. But Jessie had her hat to keep her company.
Jessie would sit in her frighteningly clean room and put on her gray hat, which almost always sagged over her eyes. She would sit there, humming a while, and a few of her real friends would appear. Her favorite was Diggory, who was a tall, thin man with a long white moustache and a squeaky voice. Diggory liked to play cards with her, a nice round of Go Fish or Old Maid. He would tell her jokes, and later, when it was time for her to go to bed, Diggory would tell her stories about where he lived. He’d sit on the edge of her bed, look vacantly at the moon out her window, and spin tale after tale of the large oak by the sea that cried golden thread whenever the stars stopped twinkling. Jessie would then hug Diggory good night, take off her gray hat, and drift away into peaceful dreams. Her parents never kissed her good night.
In school, when Jessie wasn’t allowed to wear the gray hat, she would draw pictures of Diggory, and of Annette, whom Jessie was also very fond of. One time, she drew a picture of the large oak by the sea that cried golden thread whenever the stars stopped twinkling. Her teacher grew very angry with Jessie and crumpled up the picture. “These things don’t exist, Jessica. Get your head out of the clouds,” she would snap. Jessie didn’t like her teacher very much. She was a hawkish woman, with pretty light brown hair pulled back into a forbidding bun. She wore glasses that only covered half of her extremely bulgy eyes, and she wore ugly orange blouses. But Jessie didn’t like Ms. Green because Ms. Green always said that students needed to get their heads out of the clouds. After class, Jessie stole back her picture of the large oak by the sea, and pinned it up in her room. When her father found it, he ripped it up, but Jessie saved all the scraps and taped them back together.
When Jessie was eight, her parents bought her a cat. Jessie named him Kittycat, because he was a full grown cat, but he looked like a kitty. Her parents called him Kitty, but Jessie always called him by his full name. Kittycat became Jessie’s next-best-friend, after Diggory, of course. Diggory and Kittycat got along very well. When Diggory came to play with Jessie, he’d spend a whole half hour telling Kittycat what a magnificent cat he was, and he’d run his long, white fingers through Kittycat’s fur, and let Kittycat play with the ends of his moustache. Jessie would giggle at the two, and Annette, who would sit in a nearby rocking chair, would chuckle at the antics of her friends. Jessie grew accustomed to Kittycat sleeping on her bed at night, listening to Diggory’s stories with her. Kittycat also looked very good in Jessie’s gray hat, which he would wear when Jessie went to sleep.
Jessie’s parents didn’t like Kittycat so much, though. Kittycat liked to dig through their garbage and kill mice and leave them for Jessie’s mom to find. Jessie’s parents got so angry at Kittycat, that they took him to the pound while Jessie was at school. When Jessie got home from school that day, she looked all over for Kittycat. She called for him in her room, in the living room, outside, and all around the block. When her parent’s got home late that night, Jessie cried on her mother’s shoulder about Kittycat being missing. Jessie’s father stiffly explained that Kittycat was too much of a problem for them to keep him anymore. Jessie ran upstairs and put on her gray hat, curling up in the corner of her room and crying. When Diggory asked her what was wrong, she told him, and Diggory cried too. Big, blue tears fell off the ends of his long, white moustache, and splashed on the ground. Between the two of them, they managed to create a puddle of tears.
Diggory told Jessie a story about Kittycat that night. He told Jessie about how happy he was, and how many friends he must have made. Jessie just said “But we were his friends” and rolled over and went to sleep. She didn’t even bother to take off her gray hat. Diggory sat by her side all night, crying his big, wet tears.
When Jessie went to school, she drew a picture of Kittycat, Diggory, Annette, and herself. Her art teacher, Mr. Little, who wasn’t very little at all, told her to “get your head out of the clouds”, and gave her picture an unsatisfactory. Jessie grabbed a paintbrush and threw it at his head. Jessie’s parents were called, and Jessie was suspended for three days.
For three days, Jessie sat in her room, wearing her gray hat. She sat in front of the mirror and stared at herself for hours. She was a thin, small white girl, with sickly looking blond hair and large, sad-looking green eyes. Her gray hat was too big for her, and sat lopsided on her head. Her lips were ragged, and often bloodied, and her clothes, always black, gray, or blue, were wrinkled. She stared at her mirror, and wore her gray hat, and began to imagine the life of Jessica, the girl in the mirror.
Jessica, in Jessie’s mind, was a beautiful, popular girl with eighty billion friends who all loved her. She was a talented artist, and nobody minded if she drew things that weren’t necessarily from the true planes of existence. Her parents loved her, and they never needed a babysitter. She had a cat, who her parents loved, and she didn’t need Diggory or her gray hat. Jessie envied Jessica, the girl in the mirror.
That night, Jessie put on her gray hat, and wished that Diggory would arrive swiftly, and Annette. Diggory arrived first, and told Jessie a funny joke, which made her giggle. Annette arrived soon after, and sat in her rocking chair and began rocking. Jessie sat on her bed and listened to Diggory’s jokes, played card games with him, and when it came time for sleeping, let him tuck her in.
“Tell me a story, Diggory. A really good one,” she begged, clutching her gray hat to her head, tears welling up in her eyes. Diggory didn’t seem to notice, and ho-hummed for a minute, making his moustache twitch. His eyes brightened and he looked down at little Jessie, smiling.
And he told her a long tale about a dragon and tree, and the tree asking only for a friend, and the dragon being its only friend for all eternity. Jessie cried into Diggory’s arms at the end of the story, and then looked Diggory straight in the eye and told him he was to never come back. Diggory blinked and asked her what she meant, and Jessie explained that Diggory and Annette were never to come back, that she didn’t want them anymore, that they weren’t her friends. And Diggory was very surprised and began to cry even more than he had cried when Kittycat left. He begged Jessie to let him stay, and Jessie cried too, but remained firm with her decision. Diggory clutched her tight, and Annette stared silently at Jessie while rocking in her rocking chair, and Jessie took off the gray hat, and they disappeared. Very quietly, Jessie hid the gray hat under her bed, and went to sleep.
School went swiftly for Jessie after that. She made friends with some very nice people in school, who liked her better after she stopped talking about crying oaks and flying fairies and anything weird like that. She started calling herself Jessica. In art class, she only drew realistic things, like cats and dogs and flowers. Jessica’s parents bought her two goldfish, whom she named Gold and Fish, and Ashley, her babysitter, lost weight and was eventually disposed of. Jessica’s teachers never again told her to get her head out of the clouds, and she was rewarded with good grades.
But every night, it was Jessie who would cry herself to sleep, crying for Diggory and Annette and Kittycat and all her childhood friends whom she let go of when she stopped wearing the gray hat. She never let herself wear the gray hat again, though. Not until she was turning sixteen.
On her sixteenth birthday, Jessica went upstairs to her bedroom carrying all the presents her friends and family had given her. A paint set, some books, and a nice, white hat. She sat down in front of the mirror and tried on the white hat. In the mirror, she saw Jessica, who had blond hair with volume, and beautiful green eyes that were dull, and a fair complexion. Underneath it all, though, she saw Jessie. A scared, lonely girl who still was her. Ripping off the white hat, Jessie, not Jessica, began crying and reached underneath her bed, pulling out the gray hat. She had been miserable for so long. All her life, she had tried to please others, and never herself. She had always let others tell her how she was supposed to think. Nobody had ever asked for her opinion, or what she would have liked. Nothing had changed when she had taken off the gray hat. The only thing that had changed was her, and she didn’t like it.
Pulling on the gray hat, she waited expectantly for Diggory and Annette to arrive. She sat on her bed, rocking back and forth, humming a quaint little tune, finally pacing the floor. And finally, when she thought they would never come, Diggory arrived, a bit fuzzy and very blurred, but there. He looked at her wonderingly, and squinted at her, and tilted his head to the side so that his long, white moustache touched the ground. Very slowly, he stretched out his long, white fingers and touched Jessie’s face. She smiled hopefully at him, and he began crying his big, messy tears. She walked over and hugged him, and he cried onto the top of her head. For eight years, he explained, he had sat by the large oak by the sea and cried and cried and cried, but she had never let him return. Finally, he was welcome again.
That night, they played Go Fish and Old Maid, while Annette sat in the rocking chair, watching them. Diggory told her jokes, and she laughed at them. Finally, when it was time for her to go to bed, Diggory tucked her in and told her a sad story of an elf and the river folk. She gave Diggory a hug good night, and then slipped off the gray hat and fell asleep.
The next morning, Jessie woke up and grabbed the gray hat. She put it on her head and prepared to walk to school. If her friends wouldn’t accept her for who she really was- an oddball who saw things that weren’t on the same plane of existence- so what? She was finally ready to make herself happy. She walked to school, and none of her friends noticed the hat. She told them about a sketch she wanted to work on, and how it would be an elf and a river dweller. Her friends asked her questions about it and were very interested. She told them about crying oaks and flying fairies, and they laughed, but not a mean laugh, a nice laugh.
When she drew in art class, her new teacher, Ms. Oats, praised Jessie, saying she had an eye for things no one else could see, and it was nice to see a girl that still had imagination. She hung Jessie’s artwork up all around the school, and the students and teachers liked it too. Her parents would brag about Jessie at work. And every night, Jessie would put on her gray hat, and Diggory and Annette would come, and they’d play cards and tell jokes, and finally, when it was time to go to sleep, Diggory would tuck Jessie in and tell her of a large oak by the sea that cried golden thread whenever the stars stopped twinkling. Then Jessie would take off her gray hat, which she so dearly loved, and would always love, and went to sleep.