I Volunteer | Jack Schlossberg | Friends to lovers

Wtf is going on

She didn't go out with Preston. Something in her gut told her she would just be going to spite Jack, and that didn't feel fair. Alex and Elle supported her decision, even if Alex's support was mostly biased toward the fact that she was convinced Annie and Jack belonged together.

"So if you're turning down Preston because of your feelings for Jack, what does that mean?" Elle asked Annie over the phone one night in October.

"I think it means that Jack is officially affecting my ability to date other people. And if I can't date other people..."

"Then you're finally going to try to date him?"

"Exactly." She heard Elle squeal from the other side of the phone.

"Okay so what does this look like? Like, how are you going to approach it?" 

"I guess I just have to be direct. When I've tried in the past, I got cut off or chickened out. But I just can't do that this time."

"I support this so much. You've got this."

"I fucking hope so."

The Profiles in Courage Awards were set for October 22. On the 18th she got a text from Jack. Meet at the Esplanade dock? I have a surprise. :)

See you there! she responded to Jack before sending 911 CODE RED IT'S HAPPENING to Alex, who responded with 15 heart emojis.

As she walked toward the Esplanade, her chest was burning. She was finally going to do this, for real. No more hiding or waiting, she was going to put it all on the line because she really cared. And she wanted him. And she was pretty sure he wanted her too.

When she was a few hundred feet away from the dock she could see his dark tousled hair, even though her view was partially obstructed (she'd recognize that hair anywhere). She ran her hands through her hair, adjusted her zip-up hoodie to fall slightly off her shoulder, and stepped onto the dock with a smile from one ear to the other. Her smile fell instantly as Jack came into view—or rather, as the woman with him came into view.

Sitting next to Jack was a tall blonde woman in leggings and a sports bra (much different vibe than Annie's faded blue jeans and BC sweatshirt), his arm resting on her shoulder as he watched her tell a joke. Both of them were laughing.

A moment later his eyes met Annie's, and he threw his hand up. "Annie! Over here," he said. Despite the crippling anxiety that was now coursing through her, she walked toward them. Jack stood up and stuck his arm out to give Annie a side hug. A side hug. A fucking side hug, she thought to herself.

He whispered in her ear, "It's good to see you." Then at full volume he said, "Annie, this is Courtney." The blonde woman stood up to give Annie the lightest of hugs and a pat on the back.

"And how do you two know each other?" Annie asked skeptically, her eyes wandering back and forth between the two of them. Courtney snorted.

"So, we... we've actually been seeing each other for a few months," he said, his head facing Courtney who was standing next to him. Annie's heart sank into her stomach and proceeded to melt there. "But it's been under wraps. With the whole Vogue thing, I just try to keep that stuff private."

Her mind blanked, but she knew she needed to say something. "You? The man who posts his every waking thought? Private?" she narrowed her eyes at him.

"What'd I tell you?" he said looking at Courtney again. "Isn't she funny?" Courtney sat back down onto the dock and he squatted next to her. "You going to join us?" he asked, looking up at Annie.

"Oh, I was," Annie said, racking her brain for a good excuse to leave. "But then I remembered I have like 100 things to do back at the office to get ready for next week."

Jack squinted his eyes in confusion. "But it's Saturday? I know Susan doesn't have you working on the Saturday before the busiest week of the year? She's usually a proponent of resting up before the craziness."

"No, no, it's not Susan. It's just me and my very long to-do list. I haven't managed my time very well lately," she lied.

"Oh, okay," Jack said standing up. She loved the way he towered over her. "Well, do you want any help?"

"No, no," she stuttered. "I'm all good, I swear. Just need to tie up a few loose ends." She gave Jack the best smile she could muster, but knew it was probably not very convincing. Before Jack had a chance to respond, she looked past him to Courtney and said, "So nice to meet you."

"Yeah," Courtney responded. "You too. I'll see you next week."

"Next week?" Annie blurted out before she could stop herself, the question directed at Jack.

"Yeah, she's coming to the awards as my date." For a second she could have sworn she saw an apologetic look wash over his face, but it was gone before she could be sure.

"Wonderful," she said tightly. "See you both then." As she turned and walked away, her eyes stung with tears of hurt and disappointment.

"A few months??" Alex yelled through the phone. "What the fuck does he mean 'a few months'??"

"I'm just as shocked as you are. Really," Annie said.

"But, a couple of months ago..." Alex started.

"We were in Philly together, I know," Annie interrupted in a somber tone.

"Right. He was literally making out with you. And now he's saying he had a girlfriend?"

"I mean maybe they got together after Philly. 'A few' could mean anything."

"It just doesn't make sense. He makes out with you, and then turns around and starts dating a random girl?"

"I mean Alex I did shut him down. He kind of had every right to move on."

"Why are you defending him?"

"Because I'm just trying to process everything fairly. I'm so mad, and I'm so sad, and I just have to believe he wouldn't hurt me on purpose. I need you to help me think positively about this."

"You're right, I'm sorry," Alex said. "You're a more understanding person than I am." Annie chuckled. "But let the record show that I am team Annie all the way, and that he's just made my shit list."

"Fair."

The rest of the day dragged on. All she thought about was Jack: where had she gone wrong, what signs did she miss, etc. Not to her surprise, he texted her that night.

Get everything done?

Yes!

I'm glad. Bummer that you couldn't stay, though.

Right. Sounds like I'll be getting to see more of Courtney shortly, though.

You're not mad, right? She gulped. Was he referring to her being mad that he had a girlfriend when they both clearly (maybe not always so clearly to her) had feelings for each other?

About what?

That I kept her a secret. A sigh of relief.

I mean, a heads up would've been nice.

That's fair. I'm sorry. I could tell something was off with you. She'd rather him think she was mad about the secret part (which she was) than him know she was mad that he yet again rejected her without even knowing. 

No worries.

I hope not. Can't have my girl mad at me, now can we?

She sent a screenshot of his texts to Alex along with the message What the fuck is going on.