Updated Dec 4, 2025 • ~11 min read
The drive home Monday morning felt completely different from the drive to the vineyard.
Savannah sat in the passenger seat of Barry’s car, their hands intertwined on the center console, watching the vineyard disappear in the rearview mirror.
Three days ago, they’d been friends pretending not to be in love.
Now they were… what? Together. Dating. In a relationship.
Her boyfriend was driving. She had a boyfriend. Barry was her boyfriend.
The thought made her want to laugh and cry and kiss him all at once.
“You’re doing it again,” Barry said, squeezing her hand.
“Doing what?”
“Thinking so loudly I can hear it.”
Savannah smiled. “Just processing. This weekend was a lot.”
“Good lot or bad lot?”
“The best lot.” She squeezed his hand back. “I just keep waiting for reality to catch up. For this to feel weird or wrong or complicated.”
“And does it?”
“No. That’s the scary part. It feels completely right.”
Barry brought her hand to his lips, kissing her knuckles. “We don’t have to figure everything out today. We can take it slow.”
“Slow. After ten years.”
“Okay, slower. Normal-relationship slow. Not glacial-pace slow.”
They’d said goodbye to everyone that morning. Skylar and Roman were heading straight to their honeymoon in Italy. The rest of the wedding party was scattering back to real life.
Emery had pulled Savannah aside before they left. “So. You and Barry. Finally.”
“Finally.”
“How does it feel?”
“Terrifying. Perfect. Like everything just clicked into place.”
“You two are going to be disgustingly happy together, aren’t you?”
“Probably.”
“Good. You deserve it.” Emery hugged her tight. “Don’t overthink it, Sav. Just let yourself be happy.”
Now, driving back to the city, Savannah was trying to follow that advice. To not overthink, to just be.
“So,” Barry said, breaking the comfortable silence. “Do we need to have the talk?”
“What talk?”
“The ‘what are we’ talk. The boundaries and expectations and where-is-this-going talk.”
Savannah considered. “What do you want?”
“I want you. However you’ll have me. But I’d like—” He paused, choosing words carefully. “I’d like to do this right. Take you on real dates. Meet for dinner, not just group hangouts. Hold your hand in public. Call you my girlfriend without it being a secret.”
“I’d like that too.”
“And I want to be exclusive. No dating other people, no confusion about what this is.”
“Barry, I haven’t wanted to date anyone else for ten years. I’m not going to start now.”
He smiled, relieved. “Good. Neither am I.”
“So we’re official. Exclusive. Boyfriend and girlfriend.”
“That still sounds weird to say.”
“We’ll get used to it.” Savannah shifted in her seat to face him better. “What about our friends? Do we make some big announcement or—”
“Everyone already knows. We couldn’t announce it louder if we tried.”
“Fair point.”
They stopped for coffee halfway home. Stood in line together, Barry’s arm around her waist, completely comfortable.
The barista smiled at them. “You two are cute together.”
“Thanks,” Savannah said, blushing. “We’re new at this.”
“Really? You seem like you’ve been together forever.”
After they got their drinks and settled back in the car, Barry said: “Ten years of friendship will do that. We already know each other better than most couples who’ve been married for decades.”
“Is that going to make this easier or harder?”
“Easier, I think. We’re skipping all the ‘getting to know you’ awkwardness. We already know the hard stuff—each other’s flaws and bad habits and annoying quirks.”
“You snore,” Savannah said.
“You steal all the blankets.”
“You organize your books alphabetically by author.”
“You have seventeen different coffee mugs and use the same one every day.”
“You make spreadsheets for everything.”
“You’re always exactly seven minutes late to everything.”
They grinned at each other.
“See?” Barry said. “We know all the terrible stuff. And we still want this.”
“We really do.”
The city skyline appeared on the horizon. Reality approaching fast.
“Where are you dropping me?” Savannah asked. “My place or—”
“Your place, I figured. Unless you want to come to mine?”
“I should go home. I have work tomorrow and laundry and real life to deal with.” She paused. “But maybe you could come up? Just for a bit?”
“I’d like that.”
Barry pulled up outside her apartment building forty minutes later. Helped her carry her suitcase upstairs. Stood in her living room looking suddenly awkward.
“This is weird,” he announced.
“What is?”
“Being in your apartment. We’ve hung out here hundreds of times, but now it feels different.”
“Because we’re dating.”
“Because I want to kiss you and I don’t know if that’s okay or if we’re doing the slow thing or—”
Savannah crossed the room and kissed him. Long and deep and full of answer.
“It’s okay,” she murmured against his lips. “Kissing is definitely okay.”
Barry’s arms wrapped around her waist, pulling her closer. “Good to know.”
They stood in her living room kissing like teenagers until Savannah’s phone alarm went off—reminder that she had a work call in an hour.
“I should let you go,” Barry said reluctantly. “Let you settle in.”
“When can I see you again?”
“You want to see me again? Already?”
“Always.”
He smiled. “Dinner tomorrow? Actual dinner. Like a date.”
“A first date. After ten years.”
“Better late than never.”
After Barry left, Savannah unpacked in a daze. Put her bridesmaid dress away, started laundry, tried to transition back into real life.
Her phone buzzed with texts.
Emery: How was the drive home? Did you define the relationship?
Savannah: Exclusive. Official. He’s taking me on a real date tomorrow.
Emery: CUTE. I’m happy for you.
Thaddeus: Glad you two finally pulled your heads out of your asses. Barry’s good for you.
Skylar (from the airport, apparently): Thank you for making my wedding even more romantic by finally getting together with Barry. You two are my greatest matchmaking achievement.
Savannah laughed, responding to each text. Then opened her conversation with Barry.
Savannah: Made it through unpacking without having a crisis about how my life just completely changed.
Barry: That’s growth.
Savannah: Where are you taking me tomorrow?
Barry: It’s a surprise. Dress nice. I’m courting you properly.
Savannah: Courting. You’re adorable.
Barry: I’m traditional. Sue me.
Savannah: I love you.
The words felt natural. Easy. Like she’d been saying them forever.
Barry: I love you too. See you tomorrow.
That night, Savannah lay in her own bed, staring at the ceiling, processing.
She had a boyfriend. After years of failed relationships and dating men who weren’t quite right, she was with someone who knew her completely.
Someone who’d been there for every version of herself.
Someone she’d loved for a decade.
It should feel more complicated. But it didn’t.
It just felt right.
The next day at work was surreal. Savannah tried to focus on emails and meetings, but her mind kept drifting to Barry. To their date tonight. To the fact that this was real life now—not just a wedding weekend bubble.
“You’re smiling at your computer,” her coworker Nola observed. “Good weekend?”
“The best weekend.”
“Wedding was fun?”
“Very fun. And—” Savannah hesitated. “I got together with my best friend. The one I’ve been in love with for years.”
Nola’s eyes widened. “Barry?! Finally! Oh my god, I’ve been rooting for you two forever. Every time you talked about him I wanted to shake you and yell ‘just date him already!'”
“Apparently everyone felt that way.”
“Because it was so obvious! You lit up every time his name came up. And he looked at you like you hung the moon.”
“How do you know how he looked at me?”
“Company holiday party last year. I met him. He spent the entire night watching you. It was adorable and also kind of painful because you were both so obviously in love and pretending not to be.”
Savannah buried her face in her hands. “We were really that obvious?”
“Completely obvious. But I’m happy for you! How does it feel?”
“Scary. Perfect. Like everything just shifted into place.”
That evening, Savannah changed outfits four times before settling on a dark green dress and heels. Did her makeup carefully. Tried not to have a breakdown about the fact that this was a real date with Barry.
He picked her up at seven, wearing slacks and a button-down that made her forget how to breathe.
“You look beautiful,” he said, eyes scanning her appreciatively.
“You look pretty good yourself.”
“Ready for our first date?”
“After ten years? Absolutely.”
He took her to a rooftop restaurant overlooking the city. Intimate lighting, soft music, the skyline glittering beyond the windows.
“This is fancy,” Savannah said as they were seated.
“I told you—courting you properly. That means fancy dates and opening doors and being a gentleman.”
“You’ve always been a gentleman.”
“Now I get to be your gentleman.”
Dinner was perfect. They talked and laughed and shared bites of each other’s meals. It felt like every dinner they’d ever had together, but different. Better. Because now Barry could reach across the table and take her hand. Because now she could look at him with all her feelings showing and not have to hide them.
“Can I tell you something?” Barry said over dessert.
“Anything.”
“I almost told you how I felt about fifty different times over the years. There were so many moments where I thought ‘this is it, I’m going to say something.’ And then I’d chicken out.”
“Like when?”
“Your birthday three years ago. We were at that bar with everyone, and you were laughing at something Emery said, and you looked so happy. I wanted to pull you aside and tell you I loved you.”
“Why didn’t you?”
“You’d just started dating that guy—Marcus? Mark? I can’t remember his name.”
“Marco. And I broke up with him two weeks later.”
“I know. And I almost told you then too. But you seemed sad and I didn’t want to make it worse.”
Savannah squeezed his hand. “We wasted a lot of time.”
“Maybe. Or maybe we were exactly on time.” Barry’s thumb stroked her knuckles. “We’re here now. That’s what matters.”
After dinner, they walked through the city. Hand in hand, taking their time, talking about everything and nothing.
“I should probably get home,” Savannah said eventually, even though she didn’t want the night to end.
“Probably.”
“Work tomorrow.”
“Same.”
But neither of them moved.
“Come back to my place,” Barry said suddenly. “Not for—I mean, just to hang out. Watch a movie. I’m not ready for tonight to end.”
“Okay.”
They took a cab to Barry’s apartment. Savannah had been there dozens of times, but tonight it felt different. More intimate. Like crossing a threshold.
Barry put on a movie—something they’d both seen before so it didn’t matter if they paid attention. They settled on the couch, Savannah curled against his side.
“This is nice,” she murmured.
“Yeah.”
“Feels normal. Like we’ve been doing this forever.”
“We kind of have. Just without the kissing.”
She laughed. “The kissing is a definite upgrade.”
Halfway through the movie, Savannah’s phone buzzed. Her boss, asking about a project deadline.
“I should actually get home,” she said reluctantly. “I have an early meeting.”
“I’ll drive you.”
“You don’t have to—”
“I want to.”
He drove her home, walked her to her door, kissed her goodnight like this was a normal thing they did now.
“Thank you for tonight,” Savannah said. “Best first date ever.”
“We have a lot to live up to for the second date.”
“When is the second date?”
“How about Thursday? I’ll cook dinner at my place.”
“You’re going to cook for me?”
“Attempting to cook. If it goes badly, we’ll order pizza.”
She kissed him again. “Thursday. It’s a date.”
Inside her apartment, Savannah leaned against the closed door, grinning like an idiot.
This was real.
She was dating Barry Dale.
And it was everything.
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