Week 1 — The Wynwood Escape

MONDAY – 7:06 AM · South Beach

Olivia woke up smiling, which was suspicious. For a second she didn’t remember why. Sunlight pushed around the edges of her blackout curtains, her phone buzzed somewhere under a pillow, and there was the faint hangover of too-sweet rum still clinging to her mouth.

Then she saw the text again.Leo 🌙: I’m really glad we met yesterday. Even if the timing’s complicated.

Her stomach did that little rollercoaster drop. Right. The bench. The breeze off the water. The ex.

And the sentence that had been replaying in her head since yesterday afternoon:“I don’t want to lead you on while I’m… still tangled up in someone else.”

Which was, objectively, a green-flag sentence. Mature. Kind. Responsible. And somehow it hurt more than being ghosted.

She rolled onto her back and stared at the ceiling fan.They’re going to have opinions about this one, she thought.

Talia would call him a coward. Marcus would say something like “At least he was honest.” Adrian would decide it was fate for some reason.

Her phone buzzed again. Group chat.

Talia 😒: I have a case to present at 9. Be early.
Adrian 🔥: Headline: I survived a cult initiation. Happy Hour is MINE.
Marcus 🐙: Morning. Hope everyone got some sleep. Lots to talk about today.

Olivia smiled. She typed, deleted, retyped.

Olivia 🌺: Let’s just say I met a walking green flag who still managed to wreck my mood.

Three dots appeared from Talia, then disappeared. Classic. Olivia swung her legs over the side of the bed.

Monday didn’t feel like Monday anymore. Not since they’d started this ritual a year ago. Now Monday was… the payoff. The reward for surviving the weekend.

She padded to the kitchen to start coffee, already rehearsing how she’d phrase it so it didn’t sound as pathetic as it felt:We walked. We talked. It was perfect. And then he chose someone else who wasn’t even there.

It had been Friday night, and Talia had almost canceled. The week had been long—quarter-end close, a million spreadsheets, three people who didn’t know how to attach PDFs properly, one junior analyst who thought “miscellaneous” was a valid line item for ten thousand dollars.

She’d been one thumb press away from typing, “Hey, something came up, rain check?”

Instead, she’d put on the dress. The black one that said: I am not impressed but I do have standards. She’d swiped on lipstick, scraped her hair into a clean bun, and gone to Brickell City Centre because apparently she hated herself enough to deal with valet parking and men in loafers with no socks.

“He looked normal,” she told the table, fingers wrapped around her coffee. “That was the first concern.”

“Define normal,” Marcus said. “Like his mom still texts him ‘proud of you’ sometimes,” she said. “Like he uses moisturizer. Like his laugh doesn’t sound like a war crime. Just… normal. His name was Cliff. Which, in retrospect, was foreshadowing.”

Olivia snorted. Adrian mimed writing notes in the air. They’d met at the host stand. He’d been on time, which gave him points in her internal scoring system. He’d said she looked “even better in person,” which was basic but acceptable.

“Dinner starts fine,” she went on. “He asks what I do, I tell him I’m an accountant, brace myself for the jokes, he actually says that’s cool. We order. We get into talking about travel, siblings, all the regular pre-trauma questions.”

“And then,” she said, “about halfway through the appetizer, he pulls out a notebook.”

She let the silence stretch on purpose. “In the middle of the restaurant?” Olivia asked. “In the middle of the restaurant,” Talia confirmed. “Small, black Moleskine. The kind that makes tech bros feel like philosophers. He puts it on the table, opens it, and clicks his pen.”

Adrian’s jaw dropped. “No.” “Oh yes,” Talia said. “I asked what he was doing. He says—and this is a direct quote—‘I’ve been trying to be more intentional about dating. I want to track my experiences so I can optimize.’”

Marcus made a face like he’d just bit into a lemon. “Optimize what, exactly?” “His ability to make women uncomfortable,” Talia said dryly. “He starts writing. Not like a quick note. Full sentences.”

She mimed him, looking down, scribbling, glancing at her, scribbling again. “So now I’m in a performance review,” she continued. “I decide to test this. I say, ‘What are you writing?’ with my nicest HR-voice. He says, ‘Oh, just that you made really strong eye contact when you answered my question about your parents. It might mean you have a secure attachment style but are still working on trust.’”

Olivia covered her mouth. “Talia.” “I ordered another drink,” Talia said.

Marcus shook his head. “You stayed?” “I was morbidly curious,” she shot back. “Besides, the food was good.”

It had gotten worse. He’d asked about her last relationship. Not uncommon. She’d given him the summary—dated someone for two years, realized she was more in love with his potential than his reality, broke it off, spent the next six months repairing her credit and her self-esteem.

Cliff had nodded thoughtfully. Then he’d turned another page and drawn a chart. A chart. “He had axes,” she told them. “Literal axes. X-axis was ‘Emotional Maturity.’ Y-axis was ‘Compatibility Potential.’ He started plotting points.”

Adrian slapped the table. “Absolutely not!” Olivia was wheezing. “Did he at least give you a key?” “Oh, he had labels,” Talia said. “Exes. Situationships. ‘Women who ghosted me.’ I watched him put a little dot labeled ‘Talia – preliminary’ on the graph. Right near the middle. Then he underlined it.”

Marcus stared. “You’re making this up.” “I wish I had that level of creativity,” Talia said. “The thing is, I could’ve made a joke. I could’ve said it was interesting or whatever. But something about the way he looked at me…” She hesitated, just long enough for the group to notice.

“How?” Olivia asked gently. “Like I was… data,” she said. “Not a person. A data point in his little optimization schema. ‘Woman #23: sarcastic, possible trust issues, decent eye contact.’”

She took a breath, let it out slow. “So when the check came, he said—and again, direct quote—‘I’d love to do this again. I think your long-term potential score is high, but there are some areas that need improvement.’”

Olivia whispered, “Oh my God.” “And then he showed me,” Talia said. “He had a rubric. A dating rubric. With categories. Emotional openness, long-term compatibility, sexual chemistry, financial perspective. Scores out of ten. I was… a seven point three overall.”

“Seven point three?!” Adrian yelped. “You’re at least a nine point—” “Don’t finish that sentence,” Talia cut in.

“What did you do?” Marcus asked. “I stood up,” she said simply. “I said, ‘I don’t date auditors.’ I paid for my half. I left. I blocked his number on the sidewalk.”

Silence. Then a slow, building chorus of “ohhhh” and “damn” around the table.

“That’s my story,” she finished. “Questions? Comments? Emotional damage?”

Olivia reached out and tapped her knuckles against Talia’s. “You absolutely did the right thing,” she said. “You should’ve given him a post-date survey,” Adrian muttered. “Question one: ‘On a scale from one to ten, how likely are you to never see me again?’”

Marcus smiled. “At least you caught it early. Some people don’t bring the crazy until date three.”

“Yeah,” Talia said, taking a sip of coffee. “Still feels… gross. Being graded. Like my worth was a number on his little spreadsheet.” She masked it with a smirk, but they all heard the flicker of something underneath.

They’d met in daylight, which already felt like a good sign. Most of the men Olivia met lived in dark places—bars, clubs, dim restaurants where everyone was pretending not to squint. Leo had appeared on a rooftop in Wynwood at three in the afternoon, under a sun-bleached mural and a cheap strand of fairy lights left over from some influencer event.

She didn’t even notice him at first.

Her friend Dani had dragged her to the party—“You never know, Liv, sometimes people bring friends with jobs and therapy.” There’d been the usual crowd: startup kids in branded t-shirts, artists with paint under their nails, women who somehow didn’t sweat in Miami humidity.

She had been at the bar waiting for a mojito when someone next to her said, “You look like you’re regretting every life decision that led you to this rooftop.”

She’d turned, ready with a polite laugh, and then paused. He was… nice-looking, but not in the curated way. Dark hair curling at the nape of his neck, sun-warmed skin, eyes that crinkled at the corners like he laughed a lot. Navy button-down rolled up at the sleeves. No visible chain. No ironic hat.

She’d smiled. “Wow. You’ve captured my essence in one sentence.” He’d shrugged. “It’s a gift. I’m Leo.” “Olivia.” She’d shifted her clutch from one hand to the other. “You don’t like rooftop networking either?” “I like rooftops,” he’d said. “I tolerate networking. I try not to combine the two unless there’s a strong mojito involved.”

She relayed all of this to the table with a soft, embarrassed smile, fingers tracing the cardboard sleeve of her cup. “He asked what I did, I told him marketing,” she said. “He didn’t make a single joke about ‘influencers’ or ask me to explain TikTok. He said his firm sometimes ruined the campaigns people like me worked on with bad product placements, and then he apologized on behalf of his industry.”

“What does he do?” Marcus asked. “Commercial real estate,” she said. “He called it ‘corporate Tetris.’” Talia made a face. “So he’s in the same circle of hell as Adrian.” “Real recognizes real,” Adrian said, unbothered.

“He was…” Olivia searched for the word. “‘Steady.’ If that makes sense. Like his energy didn’t take up the whole room. He asked good questions. He didn’t just wait for his turn to talk.”

She’d thought about blowing him off when he’d texted the next morning. It had felt too soon, too eager. But the text had said: “I know this is impulsive, but I’m grabbing coffee by the water later. If you want to join, I’d love the company. No pressure.”

No pressure. She’d read it three times. “So I went,” she told them. “We walked around Brickell Key. It wasn’t a date-date. No candlelight. No outfits. Just… sneakers and an iced coffee.”

She remembered the way the heat had stuck to the back of her neck, the way the water had glittered like someone had spilled sequins everywhere. They’d talked about stupid things first—favorite childhood snacks, worst concerts, whether Key Biscayne or Hollywood had the better beach.

“And then he asked,” she said. “‘What are you looking for?’ Just like that. No weird tone. Just… honestly.”

Talia rolled her eyes affectionately. “Of course he did.” “What did you say?” Marcus asked. “I said I didn’t want something casual with someone who pretended it was serious,” she answered. “That if it’s casual, we call it casual. If it’s serious, we act like it. That I’m tired of… vibes. I want… intention.”

“And?” Adrian asked. “And he said he’d been thinking the same thing,” she said quietly. “He said he was done with ‘situationships’—yes, he actually used the word—and he wanted something that felt like two people choosing each other on purpose.”

The table fell silent for a moment. “And you believed him?” Talia asked, not unkindly. “Yeah,” Olivia said. “I did.”

She’d believed him all the way to the bench overlooking the water, where they’d sat and watched a tiny yacht struggle to park itself like it was parallel parking for rich people.

She’d believed him when he’d laughed at her dumb joke about Miami being basically a resort with traffic.

She’d believed him right up until his phone rang. “It was one of those calls,” she said. “You know when someone’s voice changes when they see who’s calling? His did that. He looked at the screen, then at me, and said, ‘Sorry, I have to take this.’”

She stared at her coffee for a long second before continuing. “He walked away. Not far. I could still hear his tone, but not the words. He sounded… gentle. Tired.”

When he came back, his face had a look she’d seen before. The I’m about to disappoint you look.

“He sat down next to me,” she said, “and said, ‘I’m really glad we met yesterday. And I’ve really enjoyed this. But that was my ex. She wants to talk about getting back together.’”

Olivia could hear the echo of it in her own head. The careful wording. The guilt-edged sincerity.

“He said he didn’t want to lead me on while he was ‘still tangled up in someone else’s story,’” she continued. “That he’d been feeling unresolved about it, and if there was a chance to fix it, he had to try. That it wouldn’t be fair to me to pretend I wasn’t… in the middle of that.”

“That’s—” Marcus started. “Ugh,” Talia finished.

Olivia laughed once, humorless. “I said I appreciated his honesty. I did. I told him I hoped it worked out. We hugged. It wasn’t even awkward. And then I went home and ate an entire pint of ice cream standing over my sink like a cliché.”

She blew out a breath she hadn’t realized she was holding. “I know it’s not… evil,” she said. “I know it’s… grown-up, in a way. But it still feels like I lost a game I didn’t know I was playing.”

Marcus nodded slowly. “You didn’t lose anything. He wasn’t available. You just got the information sooner.”

“I know,” she said again. “Doesn’t mean it didn’t sting.”

Adrian pointed his coffee cup at her. “I’m just saying, if homeboy’s ex fumbles him again, he better not circle back like he’s on layaway.”

Talia’s mouth tipped up at the corner. “You did good, Liv. You were honest about what you wanted. You didn’t chase. That’s progress.”

Olivia absorbed that for a second and let herself feel a small, quiet pride under the disappointment. “Yeah,” she said. “Maybe that’s the memorable part. I didn’t beg for crumbs.”

MONDAY – 12:32 PM · Back patio

The back patio was barely a patio. More like a concrete rectangle with three metal tables, a few potted plants fighting for their lives, and a view of a parking lot.

But the light was good, and it was marginally quieter than the break room, and they could pretend the palm tree in the corner was on a beach instead of next to a dumpster.

Marcus picked at his rice bowl, more for something to do with his hands than out of hunger.

“So,” Talia said, spearing a piece of grilled chicken. “You said yours wasn’t a disaster. Which already disqualifies it from ‘most memorable,’ but we’ll allow it because your face has been weird all morning.”

“My face is always weird,” Marcus said. “More weird,” she corrected.

He sighed. Took a sip of water. Ordered his thoughts. “It was Thursday,” he started. “I wasn’t even planning to go out. I matched with her earlier in the week, we’d been messaging. She suggested meeting up last minute because she’d had a long day and ‘needed good food and better company.’”

“That’s a strong opener,” Adrian said. “Yeah,” Marcus said. “Her name’s Rina. She does UX design for some app. She showed up ten minutes late, which made me think she wasn’t taking it seriously, but she apologized and actually looked… genuinely sorry. So I let it go.”

He could still see her: curly hair piled on top of her head, big gold hoops, a sundress with little lemons on it. Someone who looked like she laughed easily.

“We went to that Mexican place in Midtown,” he went on. “We talked about nonsense first. Favorite cartoons. Worst jobs. She told me she once did data entry for a funeral home and nothing surprises her anymore.”

Talia snorted. “I like her.” “So did I,” Marcus said, a little quietly. “She asked about my job, and I tried not to bore her with server stories. She actually seemed interested.”

He remembered the way she’d leaned forward when he explained a network issue, the way she’d said, “Oh, so you keep chaos from taking over?” like it was a compliment, not a punchline.

“We split guacamole,” he continued. “She stole the last chip and apologized for being ‘competitive about snacks.’ We joked about it. It was… fun. Easy.”

“And?” Olivia asked. “And at the end of the night,” he said, “we walked to the parking lot. There was this weird little pause—you know the one where you’re like, ‘Okay, is this a hug, a handshake, or are we pretending we’re European and doing cheek kisses now?’”

“Yes,” all three of them said at once.

“I went for a hug,” he said. “She hugged back. Longer than polite, shorter than dramatic. When we pulled back, she smiled and said, ‘You’re really easy to talk to. I don’t usually give guys like you a chance.’”

He let the words hang there, exactly the way they’d been hanging in his chest for days. Olivia frowned. “Guys like what?” “Exactly,” Marcus said. “I laughed and asked her. She laughed too and said, ‘You know. Nice. Stable. I usually go for chaos. It doesn’t end well.’”

“That’s… a lot,” Adrian said slowly. “On the surface, it’s a compliment,” Marcus said. “At least I think that’s how she meant it. But it felt like… she was saying I was the safe experimental option. Not the thing she actually wants.”

He picked up a piece of chicken, put it back down. “And it got in my head,” he admitted. “Am I… ‘guys like you’? The guy you date when you’re tired of dating the guys you actually want? The intermission?”

Silence settled over the table like a blanket. Olivia’s eyes were soft. “You’re not an intermission,” she said. “She has terrible taste if she thinks chaos is more interesting than stability,” Talia said. “That’s not a you problem. That’s a her problem.”

“Still feels like… a category I didn’t know I was in,” Marcus said. “Like there’s a label on my forehead I can’t see.”

Adrian leaned back, letting out a breath. “Okay. Real talk? I’ve dated people who said stuff like that. And yeah, sometimes they mean ‘safe’ in a condescending way. But sometimes they mean, ‘I usually pick people who hurt me, and I’m trying not to.’”

“Which one do you think she meant?” Marcus asked. “I don’t know,” Adrian said. “But you’ll find out if you see her again.”

“Are you going to?” Olivia asked. Marcus picked at a napkin, shredding the edge. “She texted the next day, said she had a good time. Asked if I wanted to check out a food truck thing next weekend. I said yes.”

Talia pointed her fork at him. “Good. Go. Don’t pre-reject yourself because your brain wants to protect you from hypothetical pain.”

He looked up, startled. “That was… coherent.” “I have my moments,” she said.

Olivia smiled. “And if she does treat you like an experiment, we will absolutely drag her in absentia next Monday.” “Promise?” he said. “On my cafecito,” she replied.

The knot in his chest loosened, just a little.

MONDAY – 4:58 PM · Baby Jane – Brickell

By late afternoon, the day had done what Mondays did. There had been two server tickets, three urgent-slash-not-actually-urgent emails from Sales, one budgeting meeting where Talia had to explain the concept of “finite funds” to a grown man, and a client call where Olivia had to pretend a half-baked idea from upper management had been part of their strategy all along.

By 4:58, they were ready. Baby Jane was already humming by the time they walked in—a little bar off Brickell Ave with red lanterns, too-loud music, and a happy hour menu that had probably seen more questionable decisions than the courthouse.

They claimed a high-top in the corner. The air smelled like lime, soy sauce, and perfume. Glasses clinked; someone laughed too loud near the bar.

Adrian had been vibrating since lunch. As last week’s X-winner, he had the Happy Hour slot. The coveted finale. He’d worn a shirt that bordered on irresponsible—a soft teal that made his skin look like he lived at the beach and had never heard of fluorescent office lighting.

“Okay,” Olivia said as the first round of drinks landed. “You’ve been hyping this all day. If this story is about someone being five minutes late, I’m throwing my drink at you.”

“This story has a villain, a twist, and a moral,” Adrian said. “Respect the craft.” “Just start,” Talia said, already on her second margarita.

He took a sip of his drink, closed his eyes for dramatic effect, then opened them with a sigh. “So. Saturday night. Wynwood,” he began. “Which, in retrospect, was mistake number one. You know nothing good happens after midnight surrounded by murals and people in mesh tops.”

Olivia laughed, but it was wary. Wynwood had seen things.

“I’d matched with this girl, Asha,” he went on. “We’d been texting all week. She was… a lot. In a good way. Funny. Direct. She asked real questions. Sent voice notes. None of that ‘wyd’ energy.”

“Promising,” Marcus said. “She invites me to join her and some friends on a bar crawl,” Adrian continued. “Red flag, but I ignore it because I’m an optimist with great hair.” “No one said that last part,” Talia muttered.

He ignored her. “I get there,” he said. “First bar. She’s there before me. Big curls. Gold dress. Smile like she knows she’s the main character. I’m like—okay, I get it. This is why she’s confident enough to host a bar crawl.”

He’d walked in and seen her at a high-top, surrounded by three people already cheering. When she’d spotted him, her face had lit up in a way that hit him in the chest.

“She hugs me,” he said. “Full-body hug. Smells like vanilla and danger. Introduces me to her friends. Everything’s good. We’re drinking, dancing, making fun of a guy in a fedora. Normal Miami chaos.”

“The way you say ‘normal’ worries me,” Marcus said. “We go to bar number two,” Adrian said. “This is where things start… shifting. She gets a little quieter. Keeps checking her phone.”

There had been a tightness at the edge of her smile, like someone had pulled a string. “I ask if she’s okay,” he said. “She says, ‘Yeah, we’re fine. He’s just running late.’”

“‘He,’” Talia repeated. “Exactly,” Adrian said, pointing at her. “So I say, ‘Who’s he?’ She says, ‘Oh, my… friend.’”

He air-quoted that last word so hard it practically slapped the table. “Twenty minutes later, this guy shows up,” he said. “Tall. Beard. Button-down tucked in like he’s here to file taxes. Asha lights up. Like, different lights up. She introduces him as—‘This is Derek. My… partner.’”

Olivia groaned. “Oh no.” “So I’m standing there with a gin and tonic like the free trial that didn’t know it was expiring,” Adrian said. “She goes, ‘We’re in an open phase.’”

Talia winced. “Did she say ‘phase’?” “She said ‘phase,’” Adrian confirmed. “Derek shakes my hand. Firm grip. Too firm. ‘So you’re Adrian,’ he says. Like he’s been briefed.”

“What did you say?” Marcus asked. “I said, ‘Depends who’s asking,’ but he didn’t laugh,” Adrian said. “We all talk. Or they talk. I listen. I find out they’ve been together for four years. On and off. Or, as she calls it, ‘evolving.’”

He shook his head at the memory. “At some point she grabs both our arms and says, ‘I love you both, this is perfect,’” he said. “I’m like… I met you in person seventy minutes ago and your boyfriend looks like he hasn’t slept since Obama was in office.”

Talia took a long pull from her drink. “You stayed?” “For a while,” he said. “I was trying to be open-minded. People do the poly thing, whatever, cool. But then she starts trying to get us all to dance together. Like, literally pulls us both onto the dance floor and puts my hand on her hip and his hand on her shoulder.”

He spread his hands. “Now I’m in a trust exercise I did not sign up for.” Olivia’s eyes were wide. “Oh my God.”

“Derek looks like he’s trying to be okay with it,” Adrian said. “But his jaw keeps doing this little tic thing. She’s grinding between us like it’s a music video. I’m having a full spiritual crisis.”

“So what did you do?” Marcus asked. “I leaned down to her ear and said, ‘I’m going to the bathroom,’” Adrian said. “I walked straight out the front door. I didn’t stop. I didn’t look back. I got a hot dog from a cart, sat on the curb, and reevaluated every decision that led me there.”

Talia barked out a laugh. “You Irish-exited a throuple audition.” “I Ubered home,” he said. “Blocked her. Blocked her on the app. Blocked her in my soul. Went to bed eating french fries I found in my fridge.”

He took a sip of his drink and shrugged. “That’s my story,” he said. “I almost joined a relationship pyramid scheme and lived to tell the tale.”

The table dissolved. “That’s… oh my God,” Olivia gasped. “You were the guest star in their open-phase pilot episode.” “You were the emotional support extravert,” Marcus said. “You were the tax write-off,” Talia added.

Adrian accepted his roasting with a theatrical bow. “I’m just saying,” he said. “If you invite me out and your four-year on-and-off shows up with a vein throbbing in his forehead, I reserve the right to disappear into the night.”