Chapter 7
Lucky
I pull onto Winnie’s street in my tricked-out Chevy Tahoe that cost more than some starter homes. It’s midnight black with tinted windows, custom leather seats with baseball stitching, and wheels that gleam like they were waxed by angels.
It’s fancy and expensive but it’s just a Tahoe. A vehicle that many average American men drive. I’m staying in my “average guy” lane.
Compared to what most of the other guys on the team drive—Ferraris, Lambos, a vintage Aston Martin in Penn’s case—I’m practically low budget.
I park at the curb and look at my surroundings as I get out.
The house is tucked on a quiet, tree-lined street on the outskirts of Squirrel Hill—close enough to borrow the charm, far enough out that it might actually be affordable.
Normally, this neighborhood leans pricey, but this street feels like a hidden pocket where the real estate gods forgot to update the listings.
Winnie’s home is a small Craftsman-style bungalow with a wide porch, mismatched flower pots, and a wind chime shaped like a sun that looks like it would make the best kind of music.
It fits what I’ve observed about her—at least online and that bit of time we had this morning. Whimsical, warm, slightly offbeat.
I take a deep breath and head up to her door. She opens it before I can even knock.
“Hey,” she says, her voice clear but her expression decidedly nervous.
I will say… she looks incredible. Jeans, boots, a green cable-knit sweater that hugs her curves in the right places and makes her eyes glow like spring.
Her hair is barely past her shoulders, cut in loose layers that aren’t curly but aren’t straight either.
They sort of flow this way and that in a windblown way.
I note she’s wearing makeup, but it’s minimal and accentuates her features—full lips, high cheekbones and well… those eyes.
“Hey,” I echo. “You ready for your aggressively average date?”
She eyes the Tahoe. “That’s not exactly average.”
“What do you mean?” I ask, swinging my arm toward the SUV. “It’s a Chevy. Heartland of America and all that.”
She raises an eyebrow and nods. “It’s got custom rims and red calipers.”
“Whoa,” I say with a hum of appreciation and clutch at my heart. “You know cars.”
She smiles in a self-satisfied way before stepping out onto the porch. “My oldest brother Eli is into them. I’ve learned a few things along the way.”
“Well, my argument would be that compared to what some of my teammates drive, my SUV is practically a soccer mom minivan.”
Her laugh is quick and easy. After she locks her door, I offer her my arm. “My lady.”
Winnie snorts in a very unladylike way but slips her hand into the crook. “I think I’m already regretting this.”
“Too late,” I say as we traverse the sidewalk to my Tahoe. “You made a TikTok promise. And I brought more snacks.”
She freezes mid-step. “You brought snacks?”
“Glove compartment. Gushers and Peanut M&Ms.”
Her eyes widen. “Those are elite-level snacks.”
I open the door for her and she uses the running board to slide into the passenger seat. “Obviously. I may be many things, but snack selection is sacred.”
I make my way around to the driver’s side and note that Winnie is checking out the custom leather interior, the carbon fiber trim and stitched leather.
“I figured this was the happy medium,” I explain as I start the engine. “Still has power seats, though.”
She smirks. “My ten-year-old Honda has power seats. Big deal.”
“Exactly,” I say with a wink as we pull away from the curb.
“Where are we going?”
“I figured we’d start easy. Casual restaurant, best burgers in the city. Followed by some candlepin bowling.”
“Candlepin?” she asks, angling slightly toward me.
“The pins are skinnier. Balls are smaller. It’s weird and delightful. Very average-first-date energy.”
“It does indeed sound average,” she says. “I approve.”
We’re halfway to the burger joint before she finally asks what I was kind of hoping she’d bring up.
“So… are you going to TikTok this date?”
“I don’t know. Should we?”
She lifts a shoulder. “I’m not sure. I mean… I put this challenge out there for my followers to go on the journey with me. I envisioned me giving a summary at the end of each date, but you’re well known on the platform, so it’s not like it’s odd for you.”
“I’m cool with it if you are,” I say, and then an idea strikes. “How about we both sit down together after the date and tell everyone how it went?”
Her head turns my way, eyes illuminated by the dashboard lights and sparkling with interest. “That’s not a bad idea.”
“We can take video during the date, if you want,” I suggest. “I know to most people that would be weird, but for two elite TikTokers like us, it’s just a normal day.
” Winnie laughs and I love the rich huskiness of her voice.
“Except let’s agree no weird editing, no thirst-trap clips, unless you want a slo-mo of me bowling.
I’d be okay with that and might even flex a forearm muscle for you. ”
“Oh, please no,” she says dramatically. “Not arm porn. I’m not sure my viewers would recover.”
We laugh and I glance sideways at her quickly. “Why do you do it?”
“TikTok?”
I nod.
“I started it as a joke. Bad date venting, mostly. But then it turned into this… thing. People liked that I was unfiltered. And I realized how rare that is—being authentic. And well… that’s not hard to do, so I kept doing it. Little did I know I could make money at this gig. How about you?”
I check my rearview mirror to change lanes. “I started mine for fun. Locker room bits, chirping the guys, stupid snack reviews. Then one day I lip-synched to a Taylor Swift song and the algorithm declared me hot and funny.”
“You are funny,” she says quietly, then clears her throat. “And maybe also hot, but let’s not dwell on that.”
“Too late. You said it out loud.”
She flicks my arm and we both chuckle.
I turn into the lot of a retro diner not far from her house. Neon signs. Classic cars. Waitstaff on skates.
“You’ve been here before?” I guess.
“Only a hundred times. This place was a treat for my parents to bring me and my brothers.” I can tell by the excitement in her tone that this was a good choice. “I haven’t eaten here in a long time, though.”
Twenty minutes later, we’re seated in a retro booth lit by neon glow and string lights, sharing a basket of curly fries alongside our root beer floats.
Winnie dips a fry into her ketchup with surgical precision. “Let’s talk expectations. You’re not looking for anything serious, right?”
I chuckle as I drag a fry through her ketchup. “You’re not holding back, are you?” I glance at her as she sips her float and awaits my answer. I’m slightly distracted by her full lips that are, not going to lie, fully kissable. “Define serious,” I say.
“You know… like marriage, mortgages, joint Costco memberships.”
I fake a shudder. “God, no. I’m barely holding it together with my existing cable package.”
She snorts and nearly chokes on her drink. “Good. I like to start all first dates with a clear understanding that we’re emotionally stunted.”
“I prefer the term selectively mature,” I offer. “Like, I do my own taxes, but I also cried when I lost my AirPods.”
That gets me a real laugh and her eyes shimmer with amusement. I mean… she finds me legit funny and I love making people feel good.
We fall into an easy rhythm. She asks about the team and I ask about how she handles all those tiny humans at school. We both agree that group texts are a scourge on humanity and that brussels sprouts are a scam, no matter how much you char them and slather with balsamic.
When she’s relaxed enough to lean her chin on her hand and just… look at me, it hits hard. That spark.
Not lightning, not fire—but something hot and small that hums in my chest.
Dinner is everything a first date should be—no awkward lulls, no uneasy small talk. We dine on burgers and I learn she hates mayonnaise, loves trivia, and has an irrational fear of mannequins.
She learns I cried at the end of Finding Dory and that my mom still sends me home with leftovers when I visit her in Boston, even though I tell her it’s hard to carry on the plane.
“Tell me more about your family,” she says eventually.
“My mom’s a badass.”
“What’s her name?” she asks, and I love that she wants that level of detail. Names are personal and it shows she wants a deeper understanding of me.
“Rosa DeLuca. She’s Italian, which means she loves fiercely and has no tolerance for bullshit. All the guys call her Mama Branson.”
Her eyes soften. “What about your dad?”
“Skipped out after I was born. The only thing I have from him is his last name. My mom raised me and my older sister, Daniela, on her own. Worked two jobs, never missed a practice, still calls me every Sunday and about a dozen times in between.”
“She sounds wonderful,” Winnie says with a heartfelt sigh.
“My mom made me the man I am,” I say with deep pride. I tell Ma that all the time.
“Did she really name you Lucky?”
“No. Sadly she went with a good Italian name… Matteo. Matty to most family and friends.”
“Then where did Lucky come from?”
“I was born on a Friday the thirteenth, during a thunderstorm, and my nonna swore I was cursed. She was dramatic like that—told my mom I’d bring mayhem with me wherever I went.
But then, stuff kept going my way. Like, stupid little things.
I’d trip on a sidewalk and fall right onto a pile of leaves instead of cracking my head.
I’d find money in parking lots. I got picked to ride on the Zamboni at my first hockey game.
Just weird things that we deemed to be luck. ”
“So you were called Lucky.”