Chapter Text
Every time Gregory Bridgerton developed a crush on a girl he would write her a letter. He had no intentions of ever sending it to them, don’t get him wrong, but it became a coping mechanism for him to lay out all of his feelings without dealing with something he’s become too familiar with in the 17, almost 18 years he’s been alive - rejection.
He wrote six letters. The first one was to Lucy Abernathy, who he had a crush on for the latter half of year 7 after his very first kiss during spin the bottle. He wrote one to his brother’s wife, Kate, one to a girl from sleep away camp, and three to Hermione Watson for the three years that he’s loved her.
Gregory Bridgerton has been in love with Hermione Watson since he met her at swim tryouts freshman year. Despite his desperate attempt to keep his crush a secret, by the end of the year, their entire team and the entire school knew about the giant crush that he had on Hermione. Halfway through sophomore year, Gregory was determined that if the whole school already knew that he was in love with Hermione, he was going to do something about it. His feelings for Hermione did not dim or waver over the years. If anything, with each rejection, his fondness for her grew even more. According to his sister Hyacinth, in the three and a half years that he has known her, he has been rejected by Hermione 48 and a half times, with the half being that time he slipped and fell into the pool before he could attempt to ask Hermione if she wanted to get milkshakes after swim practice.
The more she blatantly rejected him, the longer the letters he wrote to her at the end of each school year were. He poured everything out in those letters, telling him about how he felt disconnected from his brothers on most days, with two of them being married with families of their own, and the other one trekking around the globe. He told her about his lack of experience with girls, and how he was failing AP Statistics. He even wrote about how his brother Anthony is the only father he’s ever really known.
Knowing his family, specifically his sisters , he really shouldn’t have left the letters in his desk drawer. But Gregory never claimed to be the smart one in the family. And after a particularly petty argument with Hyacinth, she sent out all 6 letters in a state of vengeance.
Obviously, he didn’t know anything about that until it was too late.
“Gregory, can we talk?” Greg looked up from where he knelt, tying his shoe. The blinding 3 o’clock sun hits Hermione’s face in a way that made her look angelic.
“Yeah, of course, Hermione,” He responded, grinning toothily at her. “How can I help you, m’lady?”
She sighed and opens her backpack, taking out three familiar-looking envelopes that varied in bulkiness. He gulped, knowing exactly what they were. “How did you get those?” He demanded.
Hermione looked at him, confused. “They were in my mailbox this morning. Listen, Gregory, I know you mean well but this is getting out of hand. How did you even know my address?”
Gregory wanted to melt into the floor. “Did you read them?” He asked, ignoring her question. He felt like he was going to faint. What the fuck was going on? This was his actual worst nightmare come to life.
She sighed again before answering. “I skimmed the first one,” she said, holding up the smallest of the three envelopes. “But if I’m being honest, even then it was all too much.”
In a flash, he reached out and ripped the letters out of her hands, breathing a sigh of relief when he saw that the letters he wrote sophomore and junior year were still sealed. Those two were more personal, and Gregory did not need Hermione reading his deepest insecurities if this was how she reacted to his first letter.
“Wha-” Hermione sputtered, surprised by his sudden movement. Undeterred, she continued. “Look, Greg, you’re a nice guy but I am just not interested in you like that. ”
Gregory stood up, and looked over the top of Hermione’s head, not wanting to hear her reject him for the 49th time. His eyes caught at a flash of white. With a jolt, he realized that it was Lucy Abernathy. And she was coming this way. Holding an envelope. Fuck.
She stormed up to them, eyes blazing. Without thinking, Gregory grabbed her and pressed his lips against hers. He felt her stiffen but did not push him away. He pulled back and wrapped his arms around her, pretending that he was embracing her so she could hear what he had to say. “Play along, please,” Gregory whispered desperately in her ear.
He pulled back and tucked a strand of her white-blond hair behind her ear. “Hey, babe.” He said to Lucy. She stared back at him in shock, but still didn’t say anything. He turned back to Hermione, arms still around Lucy. “You remember Lucy, right?” He asked, “my girlfriend?”
He knew the answer to that question. Of course, she knew Lucy. Everyone in the school remembered the blowout fight the two of them had the summer before high school. It was the talk of the school how the two of them who have been friends since birth stopped talking right before they started attending the same school again. Because of where the three of them lived in town, Hermione didn’t go to the same middle school as Greg and Lucy. He remembered hearing Lucy talk about her best friend Hermione during lunch in middle school and was shocked when Hermione laughed awkwardly and said that they weren’t friends anymore when he mentioned Lucy to her.
Hermione’s hair shot to her hairline. “Your what ?”
“His girlfriend.” It was Lucy who spoke this time, and Gregory turned to her in shock. “Well, it was great to see you Hermione but we have to go,” she said, grabbing Gregory’s hand and dragging him away.
“Where are we going?” He sputtered, almost tripping trying to keep up with her fast pace. She didn’t respond, just kept walking until they reached the bleachers by the football field. She spun around abruptly, letting go of his hand, and silently handed him back the letter.
“Thank you?” he said meekly.
She tinkered out a laugh. “What was that? Saw the letter in my hand and wanted to recreate the moment you described in vivid detail?”
He rubbed the back of his neck awkwardly, mortified at the fact that she actually read the words 13-year-old Greg put on paper. “No, no that wasn’t what that was. I’m so sorry about that. Hermione was confronting me about the letters I wrote her and it was so embarrassing Luce, my god. And then I saw you and panicked and I didn’t mean to do that but -”
Lucy held up her hand, making him stop short. “Hold on. Hermione got a letter too? And here I was thinking I was special.” She joked.
Gregory chuckled. He and Lucy have never been friends, but they got along well. “No, I wrote letters to three other people. Hermione is one of them, and another was to my brother’s wife.”
Lucy laughed, incredulously. “Kate?” She asked, before taking a moment to ponder that. “No, I get it,” she said, decisively.
“I was 14! It was before they got married!”
They drifted into comfortable silence. Lucy hummed, hesitating before she asked. “Why did you send me the letter now? Trying to shoot your shot before we graduate in a few weeks?”
Gregory laughed, amazed at how nonchalant she was being. If he got a love letter in the mail, he would be shouting it from the rooftops and would’ve posted about it on every form of social media he has, including linkedin. “Honestly I have no idea how the letters got sent out. I literally didn’t even address them. It was probably one of my sisters. Scratch that, it was most definitely Hyacinth.”
Lucy rolled her eyes at him. “So I’m your girlfriend?” She teased.
He jolted. “What?” He asked, dumbly.
“Dude, you literally kissed me and then told Hermione fucking Watson that we’re dating. Did you already forget? It wasn’t even ten minutes ago.”
“Right, yeah.” He laughed awkwardly, “sorry about that. I’ll find Hermione and tell her it was a joke tomorrow, I promise.”
Lucy didn’t respond. They lapsed into silence but it wasn’t comfortable this time. Gregory felt more and more on edge the longer she stayed quiet.
“I’m-”
“What if you didn’t?”
They spoke at the same time. Gregory gaped at her for a second, not sure if he heard her correctly. “What?” He asked, eloquently.
She blushed, before looking him square in the face. “What if you didn’t? She repeated. “We can start dating. Not for real obviously. We can just let her think that we are dating, at least for the time being.”
He stared at her, at a loss for words. “Why would you want that?”
She shrugged. “It’ll get my ex off my back for one. He won’t leave me alone.”
Gregory winced, remembering the toxic relationship that Lucy was in for the majority of sophomore and junior year. They weren’t friends, but he remembered hearing about and witnessing the numerous amount of fights the two of them would have, regardless of where they were. In the halls, at lunch, even in class.
“And, most importantly, maybe it’ll finally get Hermione to notice you. It’s been painful watching you get denied for 2 years straight,” she grinned, can not help but tease him.
“Have you ever considered law school? He asked, instead of providing an answer.
“Is that a yes or no, Bridgerton?”
“Do you think it’ll work?”
“Maybe. I’m not sure.” She hesitated. “I’ve known Hermione my whole life, though. And I can tell you with certainty that the one thing she hates is not getting attention. If a guy who’s been asking her out for the entirety of high school started dating someone she hates, she’s gonna go nuts.”
“If you think it’ll work, then I’m all in.” He said, holding out his hand for her to shake.
She shook it.