I Volunteer | Jack Schlossberg | Friends to lovers

Philly, pt. 1

3 months later

January in Boston was cold and gloomy. On most weekend days it was hard for Annie to justify leaving the house if she didn't have to. But on the third Saturday in particular, she had made plans to meet up with Alex and Michael once the two of them had finished their shifts at the library.

Once they had all gotten to their usual bar, they spent the first 45 minutes catching each other up on their lives—Alex had joined a softball team at work, Michael had just been promoted at his marketing firm (which Annie already knew, and had sent him a venmo to get lunch on his first day with his new title), and both of them were seeing new people (casually, they made clear). She had missed her friends so much, and loved hearing how well they were both doing.

When there was a dip in the conversation, Annie asked the only question she could think of. "So, how's the library?" She propped her elbow on the table and used her hand to cradle her chin.

"Annie you are there every day, you already know how it is!" Alex said back with sass.

"Well yes, but I'm locked away in my office all day. You guys are in the middle of it all."

Alex made a 'you've got a point' face. "Honestly, it's the same..."

"Not as fun without you," Michael said, interrupting Alex.

"True," Alex said, pointing at Michael.

"Well I can assure you, it's not as much fun on the weekdays without you guys either." Annie took a sip of her drink and assessed the food menu. She was contemplating mozzarella sticks.

"So... anything you want to update us on?" Alex directed her question at Annie, raising her brows up and down.

Annie chuckled. "HA, no. Same old same old."

"What does that mean?" Michael asked.

"Texting all the time, talking on the phone occasionally, sending memes. Nothing more than the usual."

"Do you know when he'll be back next?" Alex asked.

"Nope. Probably not for a while though. He won't really come back around until it's time to start planning this year's awards."

Just then, as if he'd heard their conversation, her phone lit up with a text from Jack. She picked it up, looked at the screen, looked at her friends, then looked back down at her phone. "That's crazy. It's him."

What do you have going on in March?

"He asked what I have going on in March." Alex's eyebrows shot up, and Michael suddenly had a grin on his face.

Not sure, why?

I'm giving a speech in Philly and I want you to come with me. Need my guardian angel. "Holy shit, he wants me to come watch him speak in Philly." Another buzz. I'll take care of transportation and the hotel. "He said he'd plan the travel and the hotel..."

"Hotel???" Alex gasped before Annie could even finish her sentence.

"Guys! What do I say!" Annie asked as she started to panic.

"Well, your only option here is to say yes, otherwise I might have to take you to see a doctor for insanity." Alex said.

"What if he's just asking me to go as a friend? I mean, wouldn't I be an idiot to go on a trip with someone I like knowing they don't like me back?"

"Okay first, the only person who knows where Jack's feelings stand is Jack. Second, if you want to go, you should go! Just don't put any expectations on the trip—or him," Alex said. Annie thought about it, decided she wanted to, then hit send on her text before she could stop herself. Yeah, I'm in.

Seconds later he responded, WOOOOOOO!!!

Annie flagged down the waiter. "Hi, can we get two orders of mozzarella sticks please?" Once the waiter walked off, Annie shrugged and said, "I needed something to take the edge off."

"Good call," Alex said with a wink. Michael chuckled.

On a breezy Wednesday in March, Annie stood outside of her apartment with her rolling suitcase and weekender bag sitting on top. She was wearing leggings, her oversized Maine sweatshirt, tall socks, and chunky sneakers. While she was cozy on the outside, her insides were in knots.

Jack had been texting and calling her over the last two months while he planned the trip. The closer the trip got, the more nervous she became. Because at the end of the day (literally), she was going to be staying in a hotel with—and probably sleeping in the room next door to—the man she had real, deep feelings for.

When his truck pulled up to her place, he rolled down his window and yelled, "Uber for Annie," in his most obnoxious Boston accent. He had a hat on backwards and dark sunglasses on—he looked good. She loved him like this. In his natural state. Once she was in and buckled, he pressed the gas and they were on their way to Philly. 

The first hour of the trip was designated to singing various songs from a 2000s top hits playlist. Every now and then they'd sing a ridiculous line of a song and look over at each other and giggle. Annie loved this version of herself that he brought out—the one that could let loose and sing in the car. She didn't have enough of that in her life lately.

After a particularly thrilling singalong to Boston by Augustana, Jack turned the music down and looked over at Annie with her feet up on the dash. "Annie," he said.

"Yes Jack?" she replied.

"Tell me your darkest secret." He slid his sunglasses over his forehead and up onto his head.

"Huh?" she asked, giving him an 'are you serious' look.

"You heard me. Deepest, darkest, secret. Go." He had a mischievous look on his face. It was hard for her to say no to him.

She hesitated. "Okay..." she said as she swallowed. "I'm not sure I ever actually loved my husband."

"Oh shit," he said, his head snapping toward her with a shocked expression on his face. "That's intense."

"Well... you asked," she said defensively, her face turning red with the embarrassment of over-sharing.

"No no I'm glad you were honest, I just... I don't know," he paused. "I was just expecting you to say something like you scan a honey crisp apple as a gala apple sometimes," he said as a small smirk slipped onto his face and then immediately disappeared. He glanced over at her, picking up on the embarrassment written all over her face. "Hey, thank you for sharing that with me."

She locked eyes with him. "Yeah, I mean, it's the truth. I've felt ashamed of it for so long."

"Why?"

"Because it means that whole part of my life was a lie."

"It wasn't a lie, it was a lesson," he said with a soft, genuine tone. His eyes were focused on the road again, but she saw his grip on the wheel tighten. "So, it was really that bad?"

"It was. And it wasn't. It's complicated." He responded with an mmmm sound that indicated he understood. "Okay, so now that I've bared my soul to you, it's your turn."

"I slept with my buddy's girlfriend in college." He didn't turn to look at her. Something told her he was purposefully avoiding eye contact now.

"Jack Schlossberg! Are you for real?"

"Technically," he said, holding a finger in the air, "they had broken up earlier that night, but yeah it was pretty shitty of me."

"Did he ever find out?"

"Yep. Punched me in the face." He pretended to hit his cheek with his fist.

"I'm actually shocked by this."

"Oh come on, no you're not."

"You're right, I always knew you were a slut deep down." He laughed, then held a smile, while a wave of jealousy coursed through her body.