Chapter 7 - Rooftop Cowards
Jack knew her tells.
The real ones–not the big, performative, table-banging Penelope-isms she gave to the world. He knew the quiet things.
The way she pulled her sleeves over her hands when she was overthinking. The way her laugh got a fraction too sharp when she was dodging something real. The way she tapped her fingers against the side of her water bottle when she wanted to say something but wouldn’t.
Today, she was doing all three.
And trying to pretend she wasn’t.
He watched her from across the meeting table, elbow hooked over the side of his chair, absently spinning his pen between his fingers. The room smelled like dry erase marker and burnt coffee. Leo was at the whiteboard doing unprovoked violence to a pitch deck.
Penelope was pretending to listen.
She had her chin propped on her hand, eyes on the screen, sleeve pulled all the way over her fingers so only the tips showed. Every few seconds, those fingers drummed against her water bottle. Not fast, not impatient. Just…pent-up.
She even nodded once, like she was following.
But Jack could tell her eyes weren’t tracking. They were pointed in the right direction and completely somewhere else.
“Basically, if we reposition the messaging as an experience–” Leo was saying.
Jack leaned in just enough for his voice to carry to her side of the table. “Right now it sounds like we’re launching a boutique yogurt startup,” he murmured.
Normally, that would get at least a snort. Maybe a “stop it” under her breath. Today, she barely smiled. The corner of her mouth twitched, then flattened again.
Barely.
Which meant something was very wrong.
He sat back, pen still spinning, brain already flipping through the list: sick? No. Hungover? He’d seen her hungover; that was louder. Family drama? Work? Him?
The question sat there like a stone.
—
After the meeting, she didn’t walk with him.
She always walked with him.
Usually, there was a whole routine: she’d fall into step beside him as soon as the chairs scraped back, make some crack about the meeting, bump his shoulder with her forearm like punctuation.
They’d peel off at the kitchen, or his desk, or wherever her next chaos target was.
Instead, she stayed behind talking to someone from ops.
Her posture said casual. Her sleeve-covered hands said please don’t ask me how I’m doing because I might tell you.
Jack waited at her desk anyway.
He parked by the corner and spun a slow circle in his chair like he was just…there. Not hovering. Definitely not hovering.
He checked his email. Scrolled. Didn’t read anything. Watched the hallway through the edge of her monitor.
When she finally came back, she stopped short.
“Oh,” she said. “You stalking me now?”
“Obviously.”
She rolled her eyes, but it landed a little short of its usual drama. She dropped into her chair, the wheels squeaking a little, and immediately busied herself with waking up her laptop. She didn’t meet his gaze.
He watched her type in her password wrong twice.
He leaned in slightly, forearms resting on his knees. “You mad at me?”
That got her attention.
Her head snapped up. “What? No.”
He tilted his head, studying her. “Sure?”
Penelope smiled, wide and automatic. It was the smile she used on clients. The one that didn’t quite reach her eyes. “Why would I be mad at you?”
Jack looked at her for a long second.
Then said softly, “You tell me.”
Silence opened between them.
She picked at the corner of a sticky note, worrying it with her thumb until it started to peel. “I’m just tired.”
He huffed out a quiet breath. “You always say that when something’s wrong.”
She shot him a look, a flash of her usual spark. “You always psychoanalyze me when I’m fine.”
“You’re not fine,” he said, sharper than he meant to.
It came out more like a statement than an observation. Her mouth opened, then closed again, like she’d been about to argue and thought better of it.
Jack exhaled, catching himself. He didn’t want to make her flinch. He softened his tone. “Hey,” he said, gentler. “Talk to me.”
She looked at him.
Really looked at him.
Up close, the tells were even clearer. The faint smudges under her eyes. The way her shoulders were slightly hunched, like she was bracing for something.
He watched something flicker across her face–something raw and brief and unreadable–and then it was gone.
“I don’t know what to say,” she admitted.
“Start with the part where you’re avoiding me,” he said quietly.
“I’m not,” she said automatically.
He gave her a look.
Penelope huffed out a breath, cheeks puffing. “I just… needed space.”
Jack nodded slowly, like he was cataloguing the words. “From me?”
She didn’t answer.
Her gaze dropped to the desk. A strand of hair slipped loose in front of her face; she didn’t tuck it back like she usually would.
He felt the sting of it, quick and stupid. Tried not to show it.
And he didn’t push.
Because now he really knew something was off. And it wasn’t about him being annoying in a meeting, or him missing some joke. This was bigger. Older. Whatever it was, it wasn’t starting here.
It was about whatever she saw–or felt, or realized–that she wasn’t ready to say out loud yet.
So he leaned back in his chair, stretching his arms behind his head like he was shaking it off, letting his posture go loose again on purpose.
“Okay,” he said lightly. “Space granted.”
She blinked, caught off guard. “No sarcasm?”
He smirked. “I mean, I’ll still emotionally hover. But at a respectful distance.”
That made her laugh–small, surprised, but real. It flickered like a porch light in a storm.
“Thanks,” she said.
He rolled a little closer anyway, just enough that his front caster tapped the base of her desk. Not crowding. Just…there.
“Pen?” he said.
“Yeah?”
“If you need to say something…” eyes steady on hers. “I can take it.”
She looked like she might.
He saw it. The way her throat worked. The way her hand flattened on the desk like she was steadying herself. Her eyes flicked down to his lap, to the familiar lines of his chair, to his hand resting loose on his wheel. Back up to his face.
For half a second, she really looked like she might.
But she didn’t.
“I know,” she said instead.
And he nodded.
Like that was enough.
Even though it wasn’t.
—
Apparently the universe had decided all their emotional car crashes should be staged between small plates and aggressively dim lighting.
Penelope hadn’t planned to be anywhere interesting. She was meeting her friend Rae for dinner–Rae, who insisted on “getting out of the neighborhood,” which in this case meant “walking two blocks farther than usual from the office to somewhere with twelve-dollar fries.”
“It’s that wine bar place by your work,” Rae had said. “With the hot bartenders. You can just meet me there.”
Penelope said yes because it was easier than saying she didn’t trust herself out in the world right now.
She was halfway up the elevator before it clicked.
The doors slid open into the same lobby she and Jack had rolled through that other night, when he’d casually said, “Come on, I’ll show you the good after-work spot,” and somehow they’d ended up sharing a basket of truffle tots and something that definitely wasn’t a date but also… wasn’t not.
Her stomach dropped.
Of course. Of course Rae had picked this place. God, everything reminded her of him. Pathetic.
This was his spot–the one near the office that wasn’t an accessibility obstacle course. Flat entrance, wide aisles, decent bathroom. He’d mentioned it once on their way out, almost offhand, like a private note in the margins she’d quietly memorized.
She’d just… not connected the dots when Rae said the name.
The hostess led her past the bar toward the cluster of two-tops by the windows.
And then–for fuck’s sake.
Of course he was there.
Same table she’d sat at with him. Chair angled in that familiar way to leave space. Same loose, easy posture.
He was at the end of a pushed-together cluster of tables, three other people squeezed around mismatched chairs and half-finished plates. His cousin–Pen recognized him from Instagram–sat on one side, already mid-story. On the other side, a blonde in a blazer leaned in a fraction, laughing just a little too politely at whatever Jack had just said.
Her stomach dropped so fast she had to pretend she was just adjusting her bag.
“Oh,” Rae said under her breath, following her gaze. “That’s your friend, right? The one from work?”
Penelope’s voice came out thin. “Yeah. Jack.”
He looked annoyingly good. Henley sleeves pushed to the elbow, the soft kind that showed the lines in his forearms when he lifted his glass. Hair a little messed, that lazy half-smile he only wore when he wasn’t trying.
The hostess gestured to a table a few yards away. “Here okay?”
“Perfect,” Penelope said, too fast. She sat down almost before the hostess had finished talking, as if lowering her body would somehow lower her visibility.
Rae slid into the seat opposite her, still sneaking glances. “Cute,” she said. “Built-in dinner and a show.”
Penelope’s jaw tensed. “It’s his cousin. And some friend. And some… extra friend.”
Rae’s eyebrows went up. “Territory noted.”
“I’m just hungry,” Penelope muttered.
“Uh-huh,” Rae said, unconvinced. “Well, good news, they serve food and complicated feelings here.”
Penelope smiled sweetly and flipped her off.
She tried to focus on dinner. Really. Rae told a story about her roommate’s terrible podcast. They ordered too much. They invented a backstory for the couple in the corner.
But her eyes kept drifting.
To him.
Jack was in easy-conversation mode–shoulders relaxed, hands doing that animated thing he did when he was having fun. His cousin was all-in, gesturing with his fork. The blonde wasn’t. She smiled when she was supposed to, did the polite little nods, still half-turned like she could dip any time.
Jack said something that made the table laugh, then turned slightly toward the blonde, not aggressively, just… closer. Like he’d decided the space between them was optional for the length of a sentence.
She shifted without noticing. Shoulders angled in. Elbow slid closer to the table. Her smile stopped being polite and started being real.
From across the room, Penelope watched the whole thing happen in real time–watched the exact moment the blonde went from vaguely amused stranger to oh… hi as Jack did the thing he didn’t even know he was doing.
A minute later, her fingers brushed his wrist as she reached for her glass. She didn’t snatch them back right away.
Jack didn’t flinch. He just let it happen–let it mean whatever she wanted it to mean, eyes still on whatever story he was finishing.
And Penelope felt her stomach do that annoying, unreasonable little drop like: Oh. So we’re doing this tonight.
Her fingers tightened around her glass.
Then he turned.
Of course he did.
Like some part of him had been aware of her presence the whole time and finally decided to check.
His gaze slid across the room and landed on her.
It caught hers like it had been waiting.
For one beat, everything else dropped out–the noise, the clink of cutlery, Rae’s voice, the low hum of conversation. It was just his eyes on hers and the sick, helpless sense that she’d been standing under a spotlight this whole time without knowing it.
In that one glance, she felt naked.
Jack didn’t flinch.
Didn’t wave.
Didn’t smile.
Just looked.
Long enough for her to see the recognition. The flicker of oh. The small tightening at the corner of his mouth that wasn’t quite a wince, wasn’t quite a smirk.
And that was somehow worse.
She tore her gaze away first, staring fiercely at the condensation on her water glass like it had answers.
Rae watched the whole thing happen and said nothing.
For once.
When the waiter came to take their order, Penelope picked the first thing she saw on the menu, pulse still hammering.
Across the room, Jack turned back to his table.
The blonde laughed at something he said.
Penelope forced herself to take a sip of her drink.
It burned on the way down, and not just because of the alcohol.
—
Two nights later, there was a work event–a bar thing for one of the team’s product launches. The kind where you say “just one drink” and wake up the next day in someone else’s blazer with six new Slack channels you don’t remember joining.
The place was one of those trendy rooftop bars near the office, all string lights and succulents and questionable railings. Penelope showed up in jeans and a slouchy tee that kept sliding off her shoulder. She told herself it wasn’t for anyone.
Jack wasn’t there when she arrived.
She grabbed a drink. Laughed too hard at something dumb Finn said about the app crashing “for flavor.” Let herself get pulled into a circle of people arguing about what counted as a sandwich. Pretended not to check the door every ten minutes.
When he finally rolled in, she didn’t look.
Not directly.
But her body knew.
It was like gravity reoriented as soon as he crossed the threshold. The air shifted. Her awareness snapped to the sound of wheels on concrete, the familiar sound of his front caster taking the bump by the door.
He was alone this time.
He did the rounds–clapped someone on the shoulder, let a PM hug him too long, accepted a beer he wasn’t going to finish. The whole time, he stayed on the opposite side of the room from her, like they were magnets someone had flipped.
When he passed behind her for the first time, she felt it.
The faint change in temperature as his body moved into her orbit. The soft scent of clean laundry and whatever warm, impossible thing was just him that her stomach recognized instantly.
She kept her back turned, mouth wrapped around the rim of her glass, pretending to listen to a story about someone’s dog.
They didn’t talk at first.
They orbited.
He’d be at the bar when she was by the rail. She’d move inside just as he came out. Their circles overlapped without quite touching, like the universe was dragging a highlighter over the edges of something and they were both pretending not to notice.
Then someone from marketing told a story that actually made her laugh–big, real, sharp. She threw her head back, balance tipping on the barstool. Her center of gravity shifted a little too far.
She leaned back without thinking.
Into him.
His hand caught her arm before she tipped.
Solid. Warm. Fast.
And she froze.
Jack didn’t say anything right away.
He didn’t let go, either.
His fingers wrapped around her bicep, steadying her. It wasn’t a hard grip, but it was firm enough to remind her of all the places she wanted his hands that weren’t G-rated and how much effort it was taking her not to think about that here.
Her breath caught in her throat.
She turned her head, slowly.
His face was closer than it had been in days. His brows were faintly drawn, mouth soft but serious, eyes searching hers like he could see all of it. Not just the drunk veneer. The jokes. The pretending.
All of it.
“You okay?” he asked, low.
The question wrapped around more than just did you almost fall off your chair.
She pulled away too fast, breaking his grip like it was a hot stove.
“Thanks,” she said, voice too bright. “I’m good. Gravity’s just being aggressive.”
The corner of his mouth twitched, but the worry didn’t leave his eyes. “Yeah,” he said quietly. “That happens.”
He rolled back a half-foot, giving her space that felt both necessary and awful.
She turned back to the bar.
She nodded.
But she wasn’t okay.
Not even close.
—
An hour later, the crowd had thinned a little. The music had gotten louder. The night air had gotten colder.
Penelope found herself at the edge of the rooftop patio, nursing a half-drink and pretending the wind wasn’t biting through her t-shirt. The city spread out below them, lights smeared and soft.
She wrapped her fingers around the plastic cup just to have something to do with her hands.
Jack rolled up beside her like he’d been aiming for the same spot.
He rolled up beside her and let the chair settle, fingers resting on the pushrim, front caster almost kissing the side of her sneaker. He clicked his brakes on without even glancing down. For a moment, he didn’t say anything.
Neither did she.
They just stood there, arm and shoulder almost, but not quite, touching. The air between them felt tighter than the space would suggest.
Finally, he broke the silence.
“You didn’t say hi the other night,” he said.
No accusation. Just a fact.
She kept her eyes on the horizon. “You looked...busy.”
His brows lifted, visible even in her peripheral. “You were there with someone too.”
She thought of Rae’s raised eyebrows, the way Rae had watched that whole silent exchange and politely kept her commentary to herself. She thought of the text from Brandon sitting on her phone, unanswered.
She didn’t answer him.
Jack took a sip of his drink. “She’s my cousin’s friend,” he said after a beat. “Not really my type.”
Penelope tried to sound breezy. “What is your type?”
He smiled, slow and sharp, eyes still on the city. “Still figuring it out.”
She laughed once, too loud. “Bullshit.”
That made him look at her.
Long. Quiet. Steady.
“You’re mad at me,” he said finally.
“No, I’m--” She bit the words off, jaw ticking. “I’m not mad.”
“You’re something,” he said.
She turned to face him then, arm brushing his shoulder.
“Maybe I’m tired of pretending this isn’t a thing,” she said.
The words came out before she could decide if she meant to say them, hanging there in the cold air between them, fragile and enormous.
Silence stretched.
Just the hum of the city below, the muffled thump of bass from inside, her pulse loud in her ears.
Jack looked up at her, really looked at her, like he was trying to read fine print on a document that mattered.
“What is this, Penelope?” he asked quietly.
She opened her mouth.
And for one second, just one--she almost said it.
That it hurt to see him with someone else.
That she hadn’t stopped thinking about his hand on her cheek.
That she was scared to lose him by wanting more, but more was all she could think about now.
The sentences lined up behind her teeth like a crowd at a door.
But they didn’t make it out.
Because if she said them, they couldn’t unsay them. And if she broke this–this friendship, this orbit, this thing that made every day feel like it had a pulse–she didn’t know what would be left.
So instead, she swallowed.
“I don’t know,” she whispered.
It was the smallest slice of the truth she could give him without cutting herself open.
Jack exhaled.
A slow, quiet breath that carried more than she could name. His eyes dropped to the railing, then back to her.
“Yeah,” he said finally. “Me neither.”
They stood like that for a long time.
No confessions.
No explosions.
Just a quiet, brutal kind of honesty. Two people standing on the edge of something neither of them knew how to cross, pretending the view was all they’d come up here for.
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