Chapter 5
Chapter Five
Brittany
The tiny Italian café greets us with a rush of warm air scented with garlic, tomato, and freshly baked bread.
After the biting cold of the skating rink, it feels like stepping into another world—one where my breakup with Cal doesn’t exist, where I’m not temporarily homeless, and where Weston’s smile as he holds the door for me somehow makes everything seem a little less … broken.
I’m still trying to reconcile this confident, handsome man with the awkward boy I barely knew in college. The boy with the glasses who used to hang around my big brother has transformed into someone who makes my heart flutter in ways I’m definitely not ready to acknowledge.
I’m not dating anyone anytime soon.
“This place is adorable,” I say as we follow the hostess through the dimly-lit restaurant filled with small tables covered in checkered cloths and flickering candles. Frank Sinatra croons softly from hidden speakers.
“I found it by accident during a lunch break a few years ago,” Weston says, his voice close behind me. “Best mistake I ever made.”
The hostess leads us to a corner booth partially secluded by a decorative wine rack. It feels intimate without being overtly romantic, which is … perfect, for whatever this is.
“Thank you,” I tell her as she hands us our menus.
As I slide into the booth, I realize I’m still wearing my beanie and hurriedly pull it off, probably leaving my hair looking like a static-charged disaster. I run my fingers through the blonde strands, attempting to tame them while Weston shrugs out of his puffy jacket.
“You don’t have to fix your hair,” he says, catching me mid-primp. “It looks nice like that—natural.”
I feel my cheeks warm, and it’s not because of the restaurant’s heater. “Thanks. I guess I’m just used to having it perfectly put together for work. Courtrooms aren’t exactly forgiving of bedheads.”
“I can’t imagine having to be ‘on’ like that all day,” he says, unfolding his napkin and placing it on his lap. “I’m pretty sure half the guys I work with at my office haven’t combed their hair since 2018, I think.”
I laugh, picturing a room full of disheveled programmers. “That sounds amazing, honestly. Sometimes I dream about showing up to court in sweatpants.”
“You could start a trend,” he suggests, his blue eyes crinkling at the corners. “Power sweats. Very authoritative.”
The waiter appears at our table, and Weston asks if I’d like wine. I nod, grateful for something to ease the lingering nervousness I feel.
“Red or white?” he asks.
“Red, definitely,” I reply.
Weston smiles. “A Montepulciano then,” he tells the waiter, who nods approvingly.
“Good choice, sir.”
As the waiter walks away, I raise an eyebrow. “Wow, I didn’t know you were such a wine guy.”
Weston adjusts his collar. “I’m not … it’s just one of three wines I can pronounce without embarrassing myself.”
I laugh, tucking a strand of hair behind my ear. “Well, you pulled it off perfectly.”
We fall into an easy conversation about the menu, debating the merits of classic spaghetti versus more adventurous options. Under the table, our knees accidentally touch, sending a jolt of awareness through me. We both shift quickly, creating a careful distance.
The wine arrives, and as we clink glasses, I find myself studying his face—the strong jawline, the bright blue eyes that seem to notice everything.
He looks nothing like the nerdy college kid I vaguely remember.
This version of Weston fills a space with quiet confidence, even as he makes self-deprecating jokes about his skating abilities.
“I honestly thought I was gonna break something out there,” he admits after a sip of wine. “Preferably just my pride, but possibly an actual bone.”
“You were pretty good on the ice,” I tell him.
“Pure survival instincts. I just didn’t want to embarrass myself in front of you.”
Something in his tone makes me look up sharply, but his expression gives nothing away as he studies the menu.
After we order—fettuccine for me, lasagna for him—the conversation drifts easily, and before I realize it, I’m telling him about a case I’ve been working on. A complicated property dispute with a lot of moving pieces.
“That sounds intense,” he says.
“It can be,” I admit. “But I kind of like that part.”
Weston studies me for a moment. “So, what made you want to become a lawyer?”
The question catches me off guard. I roll my wine glass between my palms, thinking. “My parents split up when I was young. And after that, everything felt … unsettled. A lot of change. A lot of tension.”
He stays quiet, giving me space.
“Parker and I were in and out of courtrooms for a while,” I continue. “Custody stuff. Meetings. Waiting rooms. We spent a weird amount of time there as kids.”
His jaw tightens slightly.
“I remember watching the lawyers more than anything,” I add. “Especially the women. They were confident. Calm. They walked into emotional situations and didn’t flinch. They asked the right questions and controlled the room.”
I lift my glass, turning it slightly. “Law felt like a way to take chaos and sort it out. Or at least try to.”
“And now?” he asks.
“And now I get paid to untangle problems.” I smile. “Which, turns out, I’m pretty good at.”
He grins. “Sure sounds like it.”
“And what about you?” I ask. “How did you get into programming?”
His face lights up as he tells me about his first computer—a hand-me-down his uncle gave him when he was nine. “It was already outdated by then, but I thought it was magic. I took it apart within a week, trying to understand how it worked.”
“Were your parents mad?”
“Furious.” He laughs. “But then I put it back together, and it ran faster than before. That’s when they realized I might actually have a thing for computers.”
I lean forward, charmed by his enthusiasm. “So, what you’re saying is … you were always a genius?”
“Hardly.” He snorts. “I once tried to ‘fix’ our microwave and nearly burned the house down. My mom still hides the screwdrivers when I visit.”
Our food arrives—steaming plates of pasta that smell divine. As we eat, our conversation flows from workplace stories to favorite books to the weirdest things we’ve seen on the New York subway. It’s so natural that I almost forget this is the first time Weston and I have really talked.
“So,” he says eventually, his tone careful, “I hope this isn’t overstepping, but … are you doing okay? With everything?”
I know what he’s asking about. The breakup. The sudden homelessness. The complete derailment of the future I thought I had.
“I’m…” I start to say “fine” automatically, but something about his genuine concern makes me pause. “I’m getting there. Some days are better than others.”
Weston nods, twirling his fork thoughtfully.
“Cal and I were together for three years,” I find myself saying. “He proposed on Christmas. I broke my apartment lease to move in with him, and three weeks later, he decided we ‘weren’t working.’” The bitterness creeps into my voice, despite my best efforts.
“That’s rough,” Weston says softly. “I’m sorry.”
“The worst part is that I didn’t see it coming,” I admit, staring into my wine glass. “I thought everything was great. I had this whole future mapped out—marriage, career path, eventual kids. And then suddenly…” I trail off, not wanting to get too deep into it.
“Sometimes the things we think we want aren’t what we need,” Weston says, surprising me.
I look up at him. “That’s … actually profound.”
He shrugs. “I have my moments. They’re rare, but they happen.”
Something about his modesty, the way he downplays his own wisdom, touches me. The restaurant’s ambient noise seems to fade as our eyes meet across the table.
“Honestly, I’m not sure I even know who I am without Cal…” I hear myself saying. “It’s so weird how you can have a whole identity wrapped up in someone else.”
I don’t mean to confess all this, not out loud. But when I risk another glance at Weston, he hasn’t looked away. In fact, he’s leaning forward, elbows on the table, as if he’s genuinely invested in whatever I’m about to confess.
And now that this idea has been articulated, it claws its way through the air, desperate to be heard.
“For so long, I was just ‘Brit and Cal.’ I let my hobbies slip away—painting, spending time with friends. It was always about … us. I prioritized him, and in the process, I lost myself. I traded late-night talks with my friends for quiet evenings where I barely spoke.”
Weston’s expression softens. “That sounds hard.”
“Honestly, I didn’t really realize it until now,” I admit. “But I feel like I’m starting over…”
“Maybe this is your chance to rediscover what makes you … you,” Weston offers gently. “You get to decide who you want to be next.”
I lean back in my chair, my thoughts swirling as his words sink in. I take a sip of the Montepulciano and then gaze at Weston, his features softened by the warm glow of candlelight. There’s a kindness in his eyes that makes me feel safe, understood, in a way I haven’t felt in a long time.
“I hadn’t thought about it that way,” I admit. “But … maybe it’s a chance to become … who I’m truly meant to be.”
Weston smiles, a genuine warmth that reaches his eyes. “You have a blank canvas in front of you, Brittany. And now, you get to paint your own masterpiece.”
I giggle at that, feeling lighter than I have all day as we finish up our meals.
“So, what about you?” I ask as I finish off my fettuccine. “Parker mentioned you’re on a mission to find ‘the one,’” I say, making air quotes.
Weston groans, covering his face with his hand. “I swear it’s not as desperate as he makes it sound. I just … I don’t know. I like the idea of having someone to share my life with.”
“There’s nothing wrong with that,” I say softly.
“Tell that to Parker.” He snorts. “He thinks I’m pathetic.”
“Parker thinks everyone is pathetic,” I remind him. “It’s his default setting.”
“True.” He laughs. “It doesn’t help that pretty much everyone I know, aside from your brother, is in a committed relationship. It’s hard not to want that, too, you know?”
“Totally.” I nod. “I mean, I honestly thought I would have kids by now.”
“Tell me about it. Now I’m gonna be an old dad. Or worse, just a funcle for all my friends’ kids.”
I raise a brow. “A funcle?”
“A fun uncle.”
“Oh my gosh.” I laugh at that. “You would be a funcle for sure, but I get what you’re saying. You want to be a dad.”
“Yeah. A fun one.” He smirks.
We both chuckle and reach for the breadbasket simultaneously, our fingers brushing over a piece of focaccia. There’s a brief pause, a moment where neither of us moves, before Weston pulls back slightly.
“You take it,” he offers.
“We could share,” I suggest, breaking it in half without thinking.
We both fall silent as we eat our halves of the bread, the flavors of rosemary and olive oil filling my mouth.
When the check arrives, we both reach for it at the same time.
“I’ve got this,” Weston says, his hand covering mine on the leather folder.
“No way,” I argue. “We can split it.”
“Please,” he insists. “It was my suggestion.”
“But—”
“Consider it a welcome back to the single life dinner,” he says with a smile that melts my resistance.
“Fine,” I concede, pulling my hand away. “But next time’s on me.”
“Deal.”