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2026-07-02
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First Date Disasters and Second Chances

Summary:

So, going on a date with Carmy should be easy. They should have dozens of things to say to each other, and they should be comfortable with each other. Because they are everywhere else. OR Carmy and Syd go on a bad first date, and get a second chance to do it over again. Inspired by "Megan and Mark" on Instagram by Ana Krutch.

Notes:

Once again, an eternal thank you to my friend PureShores for holding my hand through this and reading rough drafts of this story while I tried to work it out.

(See the end of the work for more notes.)

Work Text:


Her first date with Carmy should have been easy because she likes him a lot more than she likes most guys she has had romantic encounters with. They already have common interests, and their conversations usually flow easily when they’re in the kitchen together. Even when they’re not talking about food, and they were just being… them.

Going on a date with Carmy should be easy. They should have dozens of things to say to each other, and they should be comfortable with each other. Because they are everywhere else.

So, she doesn’t understand why they’re staring awkwardly at each other, failing to even make small talk before spilling Coke all over the white tablecloth. Syd was ready just to call it when that happened, and not because she’s embarrassed by him.

She isn’t!

She just doesn’t want to see what bad thing can happen next. She doesn’t want to stick around to see dinner come out undercooked or burned. Or to argue about whether they should split the bill or not.

And everything going wrong is so totally insignificant, it shouldn’t matter, but she’s counting down the minutes until she can leave and go home.

She’s just been starting to see the value in spending time by herself. She’ll totally be fine if she never settles down and gets married or has kids.

She will be!

She’ll get a fucking cat, even though she wants a dog more. But cats do better by themselves and don’t require as much attention as a dog, and since she’s gone all the time anyway, it’ll be more practical.

She’ll download Bumble again and pay for the friendship tier of the app, so she can find people to spend time with who aren’t her cousins or Carmy, or Richie, or Tina, or Natalie, or Marcus, or Luca.

She’ll make a nice life for herself.

She will…

But still.

Still, she was hoping that this would be something. That it could be something.

Something beautiful and wonderful.

It was just…

It was just the dating aspects and having to perform for someone. Having to be on your best behavior even when there was already history there, and they already know who you are.

And sometimes Syd does think she knows Carmy better than she knows herself.

Still, sitting across from him, while he desperately tries to make conversation with her and stumbles and stutters over his words, she’s not sure it’s enough.

She almost wishes she had never said yes when he asked her out in the first place.

She resists breathing a sigh of relief, and doesn’t argue when Carmy reaches for the check to pay without asking her. She says yes when he offers to walk her home, waits politely for him to get himself together, and does not bolt to the door.

She at least owes him that much.


“I hate dating,” Syd tells him as they stand out in front of her apartment. She grips her purse tighter in her hand. She doesn’t feel sorry about either; it’s Carmy after all. She can be honest with him; if she can tell him when he’s being an asshole, she can certainly admit this to him. She just hopes he doesn’t think it’s about him. “It’s just more of—”

“The same thing every time?” Carmy interrupts. “Yeah, yeah. I know. Not that… um, not that I’ve dated much since I broke up with Claire. I haven’t because I just-I haven’t had the time to, you know, go out that much.”

“Yeah. I-I haven’t dated that much either. Not since you broke up with Claire. Just in general,” Syd answers. “I thought… I thought it would be easier, since it was you.”

“Yeah,” Carmy agrees. “Yeah. I-I did too. I’m sorry it was so shitty.”

“Oh. Oh, that’s okay!” Syd shakes her head, reaching out and touching his arm. “Totally not your fault. I’m starting to think I just prefer spending my day off… well, not alone, but, like, without the pressure of having to be perfect to impress anybody. Because I spend my whole week trying to impress people.”

“Yeah. Yeah, I know what you mean.” Carmy runs his hand through his hair, even though on his days off, he’s still worried about impressing people. Worrying he’s not doing enough. “So, what are you going to do after I leave?”

Syd sighs. “Probably go in and eat some dry cereal, and rewatch a movie or TV show just like I always do at the end of the day. I always rewatch something these days, never anything new.”

“What kind of cereal?” Carmy asks curiously.

“Lucky Charms,” Syd admits sheepishly.

“And what will you watch?” Carmy asks.

“The 1997 Cinderella with Brandy and Whitney Houston,” Syd answers. “Have you ever seen it?”

Carmy shakes his head. “No. No, I can’t say that I have.”

“Well, you should sometime. It’s, it’s one of the best Cinderella adaptations of all time,” Syd tells him. “Although I like Ever After too. But… the 1997 Cinderella, it’s pretty damn perfect.”

“I-I haven’t seen Ever After either,” he says.

“Oh. Oh, you should watch that too sometimes,” Syd tells him. “It’s… It’s so good.”

Carmy nods. “I will.”

“This was the best part of the night,” Syd says. “It feels like… like us.”

“Yeah. Yeah, it does,” Carmy agrees, not knowing where to go after that. “Well. I’ll leave you to Cinderella and to your Lucky Charms. Uh, good night, Syd.”

“Good night, Carm,” Syd replies, her expression unreadable.

Carmy hesitates, wondering if he should lean in and kiss her cheek or hug her. But he doesn’t, mostly because it doesn’t seem appropriate after their shitty date. He wants to say something else, but he feels like lingering any longer after saying good night would be awkward, and she’s already keying in the code to her apartment building.

She spins around when she’s inside and waves at him before going to the elevators.

Carmy turns to go, once he’s confident she’s okay, and starts for home, shoving his hands in his pockets. His mind starts to wander to a handful of “what ifs”. Like what if he hadn’t tried so hard to be someone he wasn’t on their date, which in the end was par for the course with him. What if he had asked Syd if he could go in with her just for a little bit.

He sighs and stops in front of a store, contemplating whether or not he should go in and buy a carton of cigarettes. He sees a box of S’mores Lucky Charms on an endcap and wonders if Syd’s tried it yet. He thinks about going in and buying a box, backtracking to Syd’s, and giving them to her because she likes thoughtful gestures like that.

Maybe she would let him in, and they would talk some more. Maybe they would share a bowl of Lucky Charms, and she’d put on Ever After or that version of Cinderella because he’d never seen them before. Maybe he’d fall asleep on the couch, and she would cover him with a blanket, then they would have breakfast together the next morning.

He would cook breakfast for her as a way to apologize for the shitty date again. As a way to say thank you for the night before, for always giving him grace even when he’s at his worst. Maybe they would start to see each other more outside of The Bear after that, maybe they’d become more than friends. He would finally give in to all the desires for her that had been lying in wait to be noticed since the first day she walked through the door. They would touch each other, kiss, and make love. Allow himself to fall in love with her (even though he’s pretty sure he’s been half in love with her since they met).

But Carmy’s sure, like most things in his life, they would start to fight more, and say things they couldn’t take back, that they’d hurt each other beyond repair, and it would end disasterously. Just like everything in his life was prone to do.

She would hate him forever, and he would never see her again. Or he would, but things would never be the same again. He would probably have to go to her wedding, watch her with another guy, and he’d spend the rest of his life alone, pining over something he couldn’t have. Someone he couldn’t have.

Still, there’s this other part of him where he imagines that there’s this other door where things could end well. It’s something he can hardly allow himself to think about and still...

He thinks about how he’d show up with S’mores Lucky Charms, and she would invite him in… and ask him to watch a movie with her, and the exact opposite of it ending badly would happen.

They would fight, and then, surprisingly, they would make up again and again, and seek absolution from the other person just like they had every week at the Catholic church down the street from his house.

They would learn to cover up each other’s most ugly parts in gold and accept the worst parts of each other. Then one day, he would ask her to move in, to get married. To spend the rest of their lives together.

Maybe they would open a new restaurant together, a fusion of the best parts of each other. Maybe they would win awards, stars, and a James Beard. Maybe, they would have kids, mini versions of themselves running around. All girls, because he cannot see himself with a brood of boys, and he thinks girls are just nicer.

And maybe, maybe he would finally like himself after years of not.

This is something harder to accept, though.

This version of a beautiful life he’s never allowed himself to dream about. Not even when he dated Claire.

The evidence is clear enough; he’s better off by himself. The date sucked, and it’s all his fault. He’s standing alone in front of a store, debating whether or not he should buy cigarettes and cereal.

He’s so preoccupied in thought, in lives that he hasn’t lived yet or he might never live, that he doesn’t notice it has begun to rain.


Syd lets herself into her apartment and sighs as she hangs up her purse and her thrifted suede coat on the hook by her door. She throws her keys into the mint green bowl she got at a vintage flea market, and carefully takes off her heels before making her way through her dark hallway. She turns on a lamp and considers putting on her TV, but decides she wants the quiet to be able to think, especially after sitting in an overwhelmingly loud restaurant for a better part of the night.

She tries not to think about Carmy or how he looked at the end of their date.

After washing her hands, she goes to her snack cabinet and opens it, reaching for the box of Lucky Charms. She noticed there was nothing left in it besides a few marshmallows and cereal dust.

She sighs and throws the empty box away, deciding to go to the store and pick up another box. She puts her shoes back on and grabs an umbrella as rain starts to beat against the living room windows.

She doesn’t want to go out in the rain, but she doesn’t want to wait until she goes grocery shopping to get more cereal, and it’s not like she has any other snacks to replace it with either, to avoid braving the elements.

She’ll just go fast, so she can be home and dry again.

Syd’s so focused on her task, she almost misses Carmy standing in front of the store, the rain soaking him. It looks like he’s completely unaware of his surroundings or the fact that it’s raining out.

She frowns, wondering why he hasn’t gone home yet, but rushes over to him anyway, putting the umbrella over him to shelter him from the rain.

“Carm, what are you doing here?” she asks. “I thought you’d gone home, like, twenty minutes ago!”

Carmy turns around, suddenly aware of his surroundings. “Oh. Has it been twenty minutes?”

Syd pulls out her phone to check the time. “More like thirty. What are you doing out here? Didn’t you notice it was fucking raining?”

“I-I was…” Carmy trails off and looks in the window again, hesitating, not wanting to admit he was fantasizing about her even if it was in the least erotic way possible. “I was thinking about getting cigarettes.”

“Oh,” is all Syd says.

Carmy glances at her. “What are you doing out here?”

“I ran out of Lucky Charms. So I came out to buy some more,” Syd answers. She reaches out and touches his hair, completely aware of how he closes his eyes when she does. “You’re soaked.”

“Yeah, well, like you said, I-I didn’t realize it was fucking raining,” Carmy finally says, looking sheepish.

“Want to come in with me while I buy my cereal?” Syd says, letting him off the hook.

Carmy looks a little surprised at the invitation, and then he nods, slowly. “Um. Yeah. Yeah, I’d like that.”

She keeps them both shielded from the rain, and they slosh through the water, ducking inside the grocery store. They’re instantly hit in the face by air conditioning, and Syd’s skin prickles as she realizes she’s still wearing the sleeveless dress she wore on their date.

“You cold?” Carmy asks, very aware of her.

“Just a little,” Syd replies, as she snaps the umbrella shut and shakes the excess water off before putting it into an umbrella bag and putting it in a shopping cart. “I’ll be okay, though.”

Carmy nods and trails her into the store. Stopping in front of a display of S’mores Lucky Charms. “Have you had these yet?"

Syd looks up from the nectarines she’s examining and shakes her head. “No. Have you?”

Carmy shakes his head. “I don’t eat a lot of sugary cereal.”

Syd laughs and starts to fill a bag with the necatrines she was looking at. “I thought you lived on, like, Coke and peanut butter and jelly?”

Carmy shrugs and picks them up, looking at them. “Maybe I’ll try them.”

Syd nods and ties the bag off, putting them in the seat of the cart.

“Would you… uh, do you want to try them too?” Carmy asks cautiously.

“Like, do I want a box?” Syd asks, turning around to look at him.

Carmy looks a little flustered, and he rubs the back of his neck. “Fuck, I’m really fuckin’ up this whole night.”

“Carm, what are you talking about?” Syd asks, frowning as she comes over to him. “I already told you, you didn’t fuck anything up.”

Carmy blows out a breath. “I mean… do you think, maybe… I was just wondering if maybe we could try them together.”

“Oh.”

And then.

“You actually want to do that again?” Syd asks incredulously.

“No? I mean… do what again?”

“Like, go on another date?” Syd says.

“No!” Carmy answers. startling her with how forceful he was. “I just… I want to spend time with you. I like spending time with you, and I-I should have said it earlier instead of trying so hard to impress you.”

Syd thinks the way his cheeks and ears turn pink at his admission is pretty cute.

She thinks about her plans to become a lonely cat lady, and how she knows giving him a second chance would probably disrupt that. Seeing him standing in the store, under fluorescent lights, holding a box of cereal with an old Taylor Swift song playing over the speakers, she can see a different future for herself.

One that includes him in her home and her heart, not just as her co-worker.

She can see them making love in the sodium light, and how life could be good if she says yes. How life will be good if she does say yes.

Because, as God as her witness, she really does like him, even though their date was shitty, and it felt like everything that could go wrong did. And even though whatever chemistry they had seemed to have had was gone as soon as he had picked her up earlier that evening. Perfect first dates are overrated, and maybe she’s just looking for an excuse ot to pursue something.

She can feel all the blood rush to her ears, her heart in her throat as she nods. “I’d like to,” she answers.

Relief washes over his face, and he breaks into his first smile of the night. “Really?” he double-checks.

Syd pushes the cart closer to him and takes the box of cereal from his hands, putting it next to the bag of nectarines.

“Yeah,” Syd answers, her heart still beating harder than usual. She touches her chest, trying to regulate it.

“Okay,” Carmy says.

“C’mon!” Syd motions for him to follow her through the store. “I still need regular Lucky Charms.”

“Have you ever tried grilled cheese on cinnamon raisin bread?” Syd asks as they pass a display of buy one, get one free Thomas.

Carmy shakes his head, and Syd grabs two loaves, putting them in the bed of the cart.

“I’m going to make you some,” she tells him. “It’s, like, the best fuckin’ thing. Do you want to go and grab some cheddar from the deli?”

“Yeah, sure,” Carmy agrees eagerly, going off to do her bidding.

Syd wanders the aisles and adds a variety of snacks to the cart. Adds a pound of the coffee that she knows Carmy likes, flavored creamer, and regular half-and-half (just in case), even though she’s pretty sure he takes his coffee black. She picks out some peanut butter and raspberry jam, not sure what brand he buys, and wanders into the ice cream section. Carmy’s there, cheddar cheese in hand, looking at different brands, trying to decide what to get.

“You like Häagen-Dazs, right?”

Suddenly, she can see her whole future in his eyes. Little kids running around, and maybe that dog she wants. More shopping trips just like this.

“Mhm,” she answers.

“What flavor? They have this new peanut butter brittle, or do you like coffee?”

“We…” Syd trails off and quickly corrects herself, too nervous to refer to them as a ‘we’ yet. It feels premature to do that, even though technically they’ve been a ‘we’ for a long time already. “You can get whatever you’d like.”

Carmy picks a few flavors along with the peanut butter brittle and coffee, and they finally make their way to the checkout.

“Want a raincoat?” Syd asks.

“You can buy a raincoat here?” Carmy asks.

“Yeah!” Syd holds up a bright red rain poncho in a plastic bag. “Well, they’re rain ponchos. But yeah.”

Carmy chuckles and nods. “Sure.”

She rips one open when it is and helps Carmy put it on, standing back to look at him. She smiles.

“Cute,” she says, her heart fluttering a little.

Carmy opens the one for her and helps her into it, straightening the hood out, his hands lingering around her cheeks for a millisecond before pulling away.

“You too,” he answers, looking away quickly.

The checkout girl smiles at them knowingly as she scans their remaining items. Syd puts everything into her oversized boat tote and grabs her umbrella from the cart while Carmy pays for the purchases, and then returns the shopping cart to the cart bay.

“Ready to go?” he asks as he takes the bag from her, and they step out into the rainy night together.

“Mhm,” Syd answers.

He walks her home again for the second time that night, and they fall into even easier conversation this time. The shittiness from earlier in the evening is completely gone by now.

He hesitates for a second when they get to her apartment. Maybe not sure what she meant by “I’d like that” back at the store, even though she had thought it was obvious enough that she had meant tonight. Thought that he would understand that shopping together would mean she expected him to come home with her right away, and not some future date, to be decided.

“Are you coming?” she asks.

Carmy smiles at her, nods, and follows her home.

The End


 

Notes:

This was inspired by an Instagram post by Ana Krutch. I've been so obsessed with it lately.

I hope you liked it, and that you’ll leave me a comment (or kudo) if you did. I have another one-shot I’ve been working on that is probably canon divergence by now, but I’ll persevere.

Be back soon!

Until Next Time