I Volunteer | Jack Schlossberg | Friends to lovers

Hope it goes well

The Saturday after the Profiles in Courage Awards was significantly chillier than the previous week. The cool October breeze had just gotten that bite to it, and the wind speeds had increased. Annie had some time in the morning before her volunteer shift at the library, so she and Alex decided to take a walk on their favorite path along the Charles River. Annie spotted Alex's blonde pigtails and red beanie from 100 feet away.

"Look at you all bundled up," Alex said, looking at Annie's Boston College sweatshirt layered over a white turtleneck. "Very Princess Di."

"Thanks, your beanie is pretty cute too," Annie said, plucking the top of Alex's cap.

"So I'm dying to know, where did you and Jack disappear to the other night?" she asked, wiggling her eyebrows at Annie.

"First of all, Jack and I didn't go anywhere," she said sternly. "And second of all, I told you I was going to get some air and you told absolutely no one when they got worried," Annie said, playfully pushing Alex's shoulder.

"Oops," Alex said, the corners of her mouth stretching across her face. "I might've been... preoccupied."

"Well..." Annie paused, gesturing for Alex to continue on with details.

"He's so cute Annie," Alex said, jumping up in the air and clapping her hands together once. "I can't stop thinking about him. And his freaking arms. And his chest. And his abs."

Annie chuckled. "Did you at least get his number?"

"Duh! But to be fair, I got everybody's number that night. I just haven't decided what to text him yet." She took a breath, then quickly snapped her head toward Annie. "Wait, did you text Jack??"

"Hell no. What on earth would I even say?"

"I don't know, send him a picture of something at the library??"

"Tempting, but no. He asked me to get dinner with him and I said no, so that might come off as sending mixed signals if I turn around and text him."

"Annie what the hell," Alex stopped in her tracks. It took Annie about 10 steps to realize Alex wasn't right beside her anymore. When she turned back, Alex was leaning on one leg and had her arms crossed. "First you didn't tell me you met Jack, now you didn't tell me he asked you out?"

"Okay wait, I was going to tell you about meeting him, but you and Michael jumped right in to dogging on the green line. And I swear I was going to tell you about the dinner, I was just waiting until I saw you in person because I didn't want you to freak out." Alex uncrossed her arms and took a few skeptical steps toward Annie. "And he didn't ask me out, it was just a friendly dinner," Annie said in a higher octave than before.

"Can I ask why?

"Why what?"

"Why you said no?" Alex's voice softened, like she knew this might have to do with Annie's divorce and didn't want to upset her if that were the case.

"I mean, look at me," she looked down at her gray sweatpants and sweatshirt with a hole in the left armpit. "I don't think I'd mesh well into his life." Alex opened her mouth like she was about to disagree, but Annie cut her off. "Plus, my divorce isn't even legally finalized. It just felt too rushed."

"The rushed part I will give you. The other one, about you not meshing, I refuse to let you believe that."

"Alex he's a Kennedy. He wears suits and gives speeches to rooms full of millionaires. What would possibly make you think I could be with someone like that?"

"Ok yes, he does wear suits and give speeches, but he also goes to bars with his friends, paddle-boards daily, and runs around New York in his sweatpants too." Annie shot her a skeptical look. "I've seen the man's TikToks. And I know you have too," she teased, poking Annie's arm. "He's the most down-to-earth trust fund baby on the planet."

Annie chuckled. "You're right, but it still stands. I can't even think about dinner with a man right now. No matter how gorgeous his face is."

"Fair," Alex said, linking her arm through Annie's as the two continued walking up the trail.

Later that night, after she had gotten back from the library shift, Annie was cooking in her kitchen, wearing her favorite flannel pjs with a 90s country music playlist on in the background. As she pushed ground beef and peppers around a pan on the stove, she heard her phone buzz on the counter. She looked over and saw Jack's name on her screen.

I feel morally obligated to let the library staff know that you only volunteered because of the gift shop discount. She smiled right as another text came through. So sorry, my hands are tied.

Is that so? I guess I'll just have to tell your mother how much you despise speaking at the awards every year.

Hmmm, I'm almost certain I said the speaking made me nervous, not that I despised it?

I'll paraphrase.

Touché, Annie the Volunteer. She bit her lower lip as she re-read his messages. Right as she set her phone down, she heard it buzz again. Favorite bar in the city?

She thought about her answer for a few minutes. She really only ever went out with Alex and Michael after work, so she didn't know many bars. 

I feel like I should say Parla, but my real answer has to be Hopewell on Comm Ave.

Excellent choice. I'll be back in Boston in January. You, Alex, and Michael will meet me after your Saturday shift. She was stunned he remembered that detail. And somewhat flattered.

Deal. Can't wait for my dart redemption arch.

We'll see about that.

3 months later

Annie got to the bar 15 minutes early to give herself time to cool down. She'd spent the day running around town going to the laundromat, the grocery store, and the body shop for an oil change. She had just enough time to run home and change into a pair of faded jeans, a Maine sweatshirt, and her favorite New Balance shoes before getting on the T toward the bar. She sat and read her Kindle for a few minutes until she heard a familiar voice across the room.

"You know, a lobster roll in Maine might just be one of my all-time favorite foods." Her green eyes met his brown ones. When she made a confused face, he pointed to her sweatshirt.

"Oh wow! You know, I think you might actually be the first person in existence to like lobster from Maine," she said sarcastically as she stood up to greet him.

"Can you at least say hi before you roast me?" he asked, finally reaching her with his left arm stretched out for a hug. He wrapped his arm around her shoulder, and she could smell his spicy deodorant. He smelled so good. He looked so good. He was dressed in a sweatshirt and jeans, similar to her, and he also had a black ball-cap on backwards, his curls tightly tucked away tonight.

"You're early," Annie said with a smile once they were both seated.

"I'm the son of a diplomat. Of course I'm early," he grinned.

"Fair. So I meant to ask, what brings you back to Boston?"

"Oh right, the Prince and Princess of Wales are visiting the library so my mom and I are going to greet them, show them around, you know just kind of hang with them." He clocked the surprised expression on her face. "You didn't know this? I figured the library staff would've told you?"

"No, I had no idea. I haven't had a shift in a few weeks, so maybe I missed the announcement?" She looked down at the table with wide eyes. "I can't believe I didn't know this! That's so freaking cool."

"Yeah, I'm pretty excited." He picked up the menu, covering his face. A moment later, he pulled the menu down to reveal only his eyes. "But I've been more excited to see you and your friends." He winked, and she felt her cheeks blush.

Just then, the door opened and her two friends walked in together. Despite the distraction, Jack and Annie didn't break eye contact until Alex and Michael had reached the table.