Chapter 6 - The Brandon Problem
Jack found out from Marcie.
Not on purpose–she just intercepted him at the espresso machine like it was a gossip toll booth.
“Just so you know,” she’d said, in that casually-concerned tone people use when they’re absolutely being nosy, “Brandon’s been… circling Penelope.”
Jack had done a neutral face. A professional face. A face that said wow, interesting intel, thank you, valued colleague, while his brain quietly set Brandon on fire.
“Circling,” he’d repeated mildly, watching the espresso drip. “Like a hawk? Or like… a Roomba?”
Marcie had snorted, delighted. “Just–keep an eye out, okay?” Then she’d patted his shoulder and floated off to spread the next prophecy.
So later, when he was halfway through a protein bar he didn’t even like, rolling toward the break room, and he caught the tail end of Brandon’s voice–low, smooth, smug in that slightly over-smiling way–
“…she said maybe. So, you know. Progress.”
Jack didn’t stop. Didn’t change pace. He just arched a brow, rolled right past, and made a mental note that Brandon talked about women like sales leads.
It didn’t bother him.
He just noticed.
The way you’d notice a bug on your windshield. Tiny. Irritating. There. And once you saw it, you couldn’t unsee it.
He found her later, of course. At her desk, half-curled in her chair like she was trying to win a posture competition in reverse, hoodie strings knotted, hair up in something that had definitely started life as a bun.
When she saw him, she grinned.
He tossed a foil-wrapped granola bar onto her keyboard. “For the pre-lunch rage crash.”
Penelope narrowed her eyes at the wrapper. “What flavor?”
“Desperation and light judgment.”
“Perfect.”
She unwrapped it without question, took a bite, and leaned back, chair squeaking. Jack rolled up beside her desk, thumb idly tapping the handrim, popped the tab on his LaCroix, and said it casually:
“So. Brandon, huh?”
She paused mid-chew.
He didn’t look at her. Just took a sip like it was plot fuel.
“I didn’t say yes,” she said.
He gave a solemn nod. “No, yeah. Just ‘maybe.’ Which is famously nothing.”
She squinted at him. “Where’d you hear that?”
He finally turned to her, one brow raised. “Penelope. Your dating life has its own Slack channel.”
She snorted. “That’s horrifying.”
“Deeply,” he agreed. “I’m just saying, if you’re going to accept dates from Legal, you should at least announce it like an adult.”
Her mouth opened. “I didn’t accept it.”
“Yet,” he added, smooth as ever. “I’m just prepping for the day I see you in a blazer and ballet flats and know the end is near.”
A smirk. “So you are making fun of me.”
“Only a little,” he said. “It’s not your fault he’s a sentient LinkedIn profile.”
She laughed, head tipping back. And Jack? Jack leaned back in his chair like he was completely fine. Like none of this tugged at anything deeper than surface-level ribbing.
But Penelope noticed the way he didn’t look at her when she stopped laughing. The way his fingers tapped a little too steadily on his wheel rim. The way his smile lingered a beat too long, like he wasn’t ready to let it drop.
“You know I wasn’t hiding it from you,” she said, quieter now.
Jack met her eyes then. Held them. Something flickered there and smoothed out.
“I know.”
Beat.
“I mean, if you were, you did a terrible job,” he added lightly. “You know Marcie gossips faster than she breathes.”
Penelope folded her arms. “So what, are you mad?”
Jack blinked, genuinely confused for half a second. “Mad? No. Why would I be mad?”
She opened her mouth, didn’t have an answer, closed it again.
He gave her a slow grin. “Come on. I’m not mad. Just mildly devastated. I’ll recover.”
She studied him, trying to see where the joke ended. “You’re annoying.”
“You like it.”
Penelope made a dramatic sigh and stood up, stretching. Her hoodie rode up a fraction at the hem, exposing a thin strip of skin, and Jack definitely noticed. But he didn’t comment. He just bumped her hip lightly with his elbow as she stepped past him.
“You gonna go?” he asked.
She paused. “To the drink?”
He nodded, eyes back on his can.
“I haven’t decided yet.”
Jack smiled at the LaCroix tab. “Well, if you do, let me know how many times he says ‘synergy’ before dessert.”
She threw a pen at him.
He caught it, easy, without looking. Flicked it back onto her desk like nothing.
Later that night, Penelope lay in bed with the lights off and her phone glowing beside her, Brandon’s “just checking in :)” text sitting unread at the top of the screen.
She typed a reply. Deleted it. Typed another. Deleted that too.
She thought about Jack’s face. His voice. The way he didn’t flinch. The way he joked instead of asking anything he didn’t want the answer to. The way he’d said I’m not mad like he’d rehearsed it.
And somehow, that stayed with her longer than the maybe-date ever could.
—
Penelope picked the restaurant on purpose.
Across town, borderline inconvenient, dim lighting, no one from the office would ever accidentally be there unless they were having a secret affair or planning to flee the country.
Perfect.
Brandon was already at the table when she walked in—button-down sleeves rolled neatly, watch glinting, hair a little too considered, smiling like the date already counted as a win.
He stood when she arrived. Points for that. She tried to make her face match the effort.
“Penelope,” he said warmly.
“Brandon.” She smiled. It felt… functional.
They sat. Menus. A joke about traffic. A comment about the wine list. Words happening in the correct order.
He wasn’t boring.
He wasn’t rude.
He was fine.
Which somehow made this worse.
Penelope listened. She laughed when she was supposed to. She tried to be present.
But the whole time there was a faint buzzing under her ribs, like being in a room with no windows and a light that hummed.
And then--while reaching for her water--her head turned.
And the world narrowed.
Jack.
What the fuck?
Not five tables away.
He was angled slightly toward a blonde woman across from him, chair tucked cleanly into the space at the end of the table, hand resting easy on his wheel. The woman was leaning in, elbow on the linen, fingers against her cheek. She laughed at something he said—head tipped back just enough, shoulder brushing the candlelight.
Jack smiled back.
God, that smile.
The real one.
The one Penelope earned on Tuesdays and Thursdays and during dumb meetings about brand messaging. Across the top of his monitor when she dropped a meme into his DMs at 9:03 a.m.
The one he didn’t give to just anybody.
Penelope stopped breathing.
She didn’t even decide to. Her body just forgot how.
Brandon was still talking. Something about his brothers. Or baseball. Or a dog. She couldn’t hear any of it through the static.
Jack didn’t see her.
She wished he had.
She wished he hadn’t.
She didn’t know which one would have killed her faster.
She forced herself to look at Brandon again. “Sorry - what were you saying?”
He smiled, easy. “Just that I used to ump Little League. Nothing important.”
She nodded, tried to smile, tried to climb back into the conversation like nothing in the room had shifted on its axis.
But her gaze kept flicking back to Jack.
The blonde reached out—casual, unhurried—and touched Jack’s forearm as she laughed. Her fingers stayed there, light against his sleeve.
Penelope’s heart did something that felt physically impossible - like folding in on itself.
The woman wasn’t doing anything wrong.
She wasn’t dramatic.
She wasn’t overplaying it.
She was just… interested.
And Jack…
He looked comfortable.
Not flirty.
Not performing.
Just… open. Relaxed in that way he got when he decided a space was safe and worth the effort.
Penelope’s hand clenched around her napkin under the table until the fabric twisted tight between her fingers.
Brandon asked her a question. She didn’t hear it.
“Sorry--can you repeat that?” she managed, voice a half-second behind her mouth.
He chuckled softly. “You okay? You seem… somewhere else.”
She swallowed. “No, I’m here.”
But oh god, she wasn’t.
She was at a taco truck on a Tuesday.
At a break room heater with cold fingers.
On her couch playing video games with a man who teased her about granola bars and let her wear his hoodie without asking for it back.
She was everywhere but here.
The blonde leaned in again. Jack ducked his head slightly, smiling in that warm, quiet, I like being seen way that hit like a punch when it wasn’t aimed at her.
Penelope’s throat tightened.
Brandon noticed her distraction this time. He looked behind him.
“Oh,” he said softly. “That’s Jack, right? From product?”
Penelope didn’t answer.
Brandon took his time. Not smug. Not jealous. Just observant.
“He’s great,” Brandon said. “Everyone likes him. Good energy.”
She hated how true that was.
“Looks like a date,” Brandon added gently.
A beat.
Penelope forced a small smile. “Yeah. Looks like it.”
She took a slow sip of her drink.
Didn’t look away.
Didn’t blink.
Just watched the woman laugh again, hand still resting near Jack’s, watched him lean in a fraction to hear her over the noise, the soft give of his shoulders.
And tried very, very hard not to understand what that meant.
—
Penelope walked into her apartment and didn’t turn the lights on.
The door clicked shut behind her. The silence felt thick—like her place had been waiting for her to arrive with something heavy. Like it knew.
She dropped the little cardboard leftover box on the couch and just… stared at it. The perfectly adequate pasta. The perfectly adequate date.
Brandon had offered to walk her to her car. He’d opened her door, even asked if she got home okay.
She’d smiled. Thanked him. Said she’d had a nice time.
She lied.
Not because the date was bad.
Because it wasn’t.
And that made it worse.
She stood in the middle of her living room for a long time. Jacket still on. Purse still hanging from her shoulder. Keys still in her hand.
The memory of Jack’s laugh still echoing under her skin.
That woman’s hand, resting on his arm.
That softness in his face.
Goddamn it.
Penelope peeled off her jacket like it was too tight and tossed it somewhere near the chair. Her shirt came next. The bra. The boots. All of it. She left a trail like she was shedding a version of herself that had tried to pretend the night was normal.
She padded into the kitchen in mismatched socks and ate two spoonfuls of peanut butter straight from the jar.
It didn’t help.
The phone buzzed at 10:42 p.m.
[Jack]
You alive?
She froze with the spoon still in her hand.
Of course he was texting her.
Of course he didn’t know.
Her thumbs hovered over the keyboard.
Saw you.
Deleted.
Nice date?
Deleted.
Why does my heart feel like it's getting ripped out of my kneecaps when another woman touches your arm?
Absolutely deleted.
She typed.
[Penelope]
Barely. Long day.
He answered instantly.
[Jack]
You go out?
Or just buried in spreadsheets and regret?
Her stomach flipped.
She could say no.
She could say yes.
She could say I was five tables away while you smiled at someone else and my soul evacuated my body like a cartoon ghost.
She went with:
[Penelope]
Bit of both.
[Jack]
Sounds about right.
I went out too.
Drinks. Okay food. Weird vibe.
Her pulse stuttered.
He knew.
Or maybe he didn’t.
Or maybe she just wanted him to..
[Penelope]
You with someone?
The dots appeared.
Disappeared.
Came back.
[Jack]
Kinda.
Not really.
A friend of a friend. Felt like a setup.
Not sure what I was doing there tbh
She stared at that for a long time. Typed:
Congrats on your date with a woman who says “namaste” while cutting you off in traffic.
Deleted.
[Penelope]
Did she laugh at your bad jokes?
[Jack]
Pen
They’re not bad.
They’re charming.
She didn’t respond.
The dots popped up again.
[Jack]
You okay?
That was the one that undid her.
Because no, she wasn’t.
Not even close.
But she didn’t know how to say it.
There was no version of the truth that didn’t sound like a confession she wasn’t ready to make. Not here. Not like this.
[Penelope]
Yeah.
Just tired.
Three dots. Then nothing.
Then:
[Jack]
Sleep.
Talk tomorrow?
[Penelope]
Yeah.
Night.
She threw her phone down face-first and crawled into bed.
She stared at the ceiling.
Her chest ached like someone had reached in and rearranged something important without asking.
She replayed the restaurant like a bad movie she couldn’t turn off.
She thought about the way he laughed.
The way the woman leaned in.
The way he looked at ease.
It shouldn’t matter.
But it did.
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