I Volunteer | Jack Schlossberg | Friends to lovers

Our thing

On October 22 Annie woke up with a massive headache. The awards started at 4 PM, but she had to be at the library at 7 AM, so she got up at 5. After she brushed her teeth and hair, she did her usual light makeup and changed into her work clothes (black trousers, white flowy top, black loafers).

She'd just sat down when her phone lit up with a text from Jack. Today's the day. Let's kill it, champ. She reacted to the text with a thumbs up, rolled her eyes, and put the phone face down on the table while she continued getting ready.

She was out the door at 6:15 and pulled into the parking lot at 6:55. The usual crowd was already there; Susan, the other museum and program directors, and the four library interns—Alex, Michael, and the other volunteers would be arriving in the afternoon to hand out programs outside. She was shocked to also see Jack there, talking with Susan. His hands were in the air and he was pointing at the stage as if he were giving her layout tips.

Despite her desire to avoid him, she walked toward them and addressed Susan. "Good morning, what are we talking about?" Annie asked.

"Good morning, Annie! I'm so glad to see you," Susan said.

"Morning sunshine," Jack said to her as she kept her sights on Susan.

"Hey Jack," she said dismissively. "Where would you like me first, Susan?" she asked.

"Actually, you stay here with Jack and take over for me. We're talking about where the press should stand. Last year they were in the way of the audience and we don't want that to happen again."

"Alright, can do," she said reluctantly as Susan began walking away. "So, what were you thinking?" she asked Jack, still facing forward.

"Can we talk first?" She could feel him looking at her, but she kept her eyes on the stage.

"What's up?" she asked.

"I haven't heard from you in four days. I was starting to get worried."

"We've gone four days without talking before, Jack," she said flatly.

"Right, but never after you've walked off when we were hanging out." Now she turned to him.

"You know what, you're right," she said sharply. "I have been avoiding you. I don't really want to talk to you. You were very inconsiderate, and you hurt my feelings." She crossed her arms over her chest. "There, does that make you feel better?"

"No, it doesn't actually." He crossed his arms over his chest as well. "You told me everything was fine?"

"Well, I thought about it some more and I changed my mind."

"Well that's not fair."

"Neither is having a secret girlfriend and not telling someone who considered you their best friend about it." His face lit up.

"I'm your best friend?" he asked softly. Her face went blank.

"Yeah, so what."

"You're mine too, Annie." A smile climbed up his face, then fell slightly. "Which is why I'm so sorry I've hurt you. I really didn't mean to."

She turned back to face the stage. "It's fine. But we really need to tackle this press issue or I might lose my job, and then it won't be fine."

The rest of the morning went by productively. Annie got pulled away by Susan to talk with the press, so she (luckily) didn't have to interact with Jack for a few hours.

At some point Jack snuck off to go get ready, and when he returned he walked in with his family in tow—and Courtney by his side. Her glossy blonde hair was down to her elbows, and she was wearing a sleek black dress with a sweetheart neckline and no jewelry. She was very much giving Carolyn Bessette Kennedy, and it made Annie roll her eyes without even realizing.

As Annie was sorting through pamphlets and programs, she saw two tall figures step into her line of sight. As much as she hated it, she couldn't help but think that they looked good together.

"There she is," Jack said playfully punching her arm.

"Hi Jack," she said with a fake smile plastered on her face. She turned her head to face Courtney. "Hi Courtney, it's nice to see you again."

"Likewise," Courtney said cheerfully. "I'm going to go find the ladies room, I'll meet you at our seats," she said, planting a kiss on his cheek. The temperature of Annie's blood increased by at least 50 degrees.

"Hey I just wanted to ask again if you were okay. I'm sorry to be a broken record, I just keep upsetting you without meaning to." His tone was so earnest that she almost felt bad for being upset.

She sighed, then gave a small, genuine smile. "We're fine, Jack. I promise." He returned her smile, and placed his hand on her upper arm.

"I'm really glad," he said. Their eyes stayed locked for a few seconds before she finally looked away.

Jack didn't stick around after the awards this year. He, his family, and Courtney left shortly after the ceremony to have dinner with some other very important people that Annie didn't recognize.

The whole night she had been an anxious mess, barely keeping it together, and it had nothing to do with the event and everything to do with Jack. On her drive home she called her sister and ranted about what an asshole he was, and how much he hurt her. Her sister listened but was wise enough not to interject. She knew Annie didn't really feel this way, she was just in the heat of the moment.

Despite the anxiety, Annie was able to fall asleep fairly quickly. She slipped into a deep sleep, and was woken up only by a knock at her door the next morning. "Just a second," she said, groggily.

She looked at the clock—10 AM—and threw on a sweatshirt and her glasses before opening the door. When she saw him standing there, she felt like the breath had been knocked out of her for a second. "Jack?" she asked, confused.

"Expecting someone else?" he chuckled, tilting his head to the side.

"No, no... I just... where's Courtney?" Annie's eyes started to wonder around the hallway.

"She's back at the hotel. This is just our thing, you know?"

"What's our thing?"

He revealed the brown paper bag that he'd been hiding behind his back. "I got two bacon this time." He winked.

"So how'd you meet?" Annie asked reluctantly as the two of them ate their sandwiches on her coffee table.

"Her parents know my parents, so we'd kept each other company through a few boring dinners." Of course she has rich, connected parents, Annie thought. "But then I saw her at another dinner in April and the conversation just really clicked that time for some reason."

"April?" Annie asked, her heart sinking.

"Yep," he said, blissfully unaware how much she was hurting. After a few moments of silence he said, "I know you'll like her once you get to know her. She's really fun." Annie replied with a low mmhmmm and took a bite of her sandwich to avoid responding. "In fact, I was thinking maybe next month we could make a trip back up here and the three of us could get dinner."

"The three of us? Why?" Annie asked.

"So you can get to know her," he said matter-of-factly. 

"Why is it so important that I get to know her?"

"Because it means a lot to me?" he asked, confused.

"But why? Why do you care if I like her or not?" Annie knew she was getting unnecessarily defensive, but she couldn't stop herself.

"Because you're my best friend, and she's my girlfriend. And I would love it if the two of you could be friends."

"Jack, I'm happy for you," she lied. "But please don't put an expectation on me to be her instant bestie. That's not fair." Her words came out harsher than she meant for them to, yet she still added, "You picked her, I didn't."

"You're right. Will you just promise me you'll try to get to know her? You don't have to like her... yet."

"Yes. I will try." No, she wouldn't.