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You've Got Mail

Summary:

When David finds a Craigslist Missed Connections ad about himself, he decides to reach out to the person who posted it, starting an email chain that just may change his life.

Notes:

Inspired by a very real Craigslist missed connections post and by the seminal 1998 romantic comedy directed by Nora Ephron that shares its name with this fic.

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

Chapter 1: Chapter 1

Chapter Text

“David!” Alexis called from the bathroom before sauntering out of it. David looked up from his place at the table, where he’d been staring at a small mirror and patting in his skincare. She frowned at him wordlessly, her phone trapped between her hands.

“What, Alexis?” he said with annoyance colouring his voice.

“David, I think this Missed Connections ad is about you.”

He made a face at her. “What? Those Craigslist things? Ew, why are you on there?”

“Oh my god, it’s just, like, a self-esteem thing for me to count how many Missed Connections ads are about me. Anyway, I think this is about you. From when we stopped at that Tim’s in Toronto?”

David frowned but acquiesced and stood up to take a look. He grabbed her phone from her hand, ignoring her scoff of frustration, and focused on the message.

“‘Tall brown-eyed traveller dressed in black at Tim Horton’s’?” he read aloud incredulously. “Alexis, that could be anyone.”

“Oh my god, David, keep reading!”

The probability of you reading this and replying are slim but here we go. I saw you today, the first day of summer, at the Tim Horton’s on Bay and Bloor at approximately 1:45 pm.

You were arguing with a girl, your sister, I guess. You were dressed in black and were carrying a black messenger bag. You seemed to be travelling; at least, that was the impression I got. You left a few minutes after you got your order. You were in line behind me and you seemed like the kind of guy I’d like to talk to forever.

I hope you find me. More than likely not through this attempt, but hopefully out there in the world.

Until then.

David’s heart twinged a bit; he’d been used to being noticed, sure, by paps or beautiful strangers who had expensive bar tabs, but he was never noticed like this. Like someone had seen him and thought he had more to offer than a good lay and a night of free drinks.

“We stopped there on our brother/sister date, remember? And we were arguing about the chocolate hazelnut croissants?” she asked hesitantly, prodding at his memory.

“Ew, don’t call it that. I think the town sign is rubbing off on you,” David said with a grimace.

“Ew, David! Shut up!”

“Also, I still think those croissants are worth the calories,” he insisted absentmindedly, suddenly lost in thought. Who was in line at that register with them?

“Whatever, David. But I still think this person’s talking about us.”

David fixed his gaze on her. “Do you remember who we were behind in line?”

She frowned and looked back at the screen. “Ummm, no. I don’t think so.”

David groaned in frustration. “Goddammit, Alexis, now I’m gonna be thinking about this all day!”

She smiled at him wickedly. “Well, David, there’s one sure way to figure out who this is.”

He raised an eyebrow at her and watched, aghast, as she hit the “Reply” button and an email textbox popped up.

“Oh, no. No, no, no, absolutely not. Are you serious?”

She shrugged and pushed the phone into his chest. “Listen, whatever happens, you could either get laid or make a friend. And god knows you need them, since Stevie’s literally your only friend.”

“Stevie’s not my only friend! I have...other friends here.” he said defensively, hands waving about.

“Mhmm, sure, David. Except I don’t think that just because Twy knows your coffee order, you can consider her a friend,” she replied, looking at him pitifully.

“Go swallow a steak knife.”

She rolled her eyes and took the phone back to text him the link to the ad. “It’s on your phone if you want it.” She turned then to leave and bother their parents with something.

“I don’t! I don’t want it!” he called after her.

That night, when he was snuggled up in bed—well, as snuggled up as one could be on a mattress as hard as a tombstone—he scrolled through his contacts list. All his text messages from the last few weeks were from Stevie, Alexis, his parents, or Roland.

He sighed. Maybe it couldn’t hurt. He tapped the link Alexis texted him and read through the ad again before hesitantly tapping the “Reply” button. At the very least, if he did follow through with this, he wouldn’t be giving that much about himself away. He made sure to use his personal email—[email protected]—which was nondescript enough and a vestige from the days when AOL was still widely used.

He sat up in bed, staring blankly at the cursor in the empty textbox that seemed more menacing with each blink. He ran his hands through his hair, frustrated. Had it come to this? Really? Answering Missed Connections ads on Craigslist? How had he fallen so far?

He spent an hour talking himself out of it, then talking himself back into it again. Maybe it wouldn’t be so bad. He could use a friend. Maybe this could be, like, a texting relationship. Or an email thing, like in You’ve Got Mail. He bit his lip at the thought. Maybe there was a charming 1998-era Tom Hanks waiting for his email, fifty miles away. He put his phone down and leaned over in his bed, his hand searching blindly underneath it until he finally unsheathed the bottle of vodka he’d snuck into the room for dire situations. This could be considered an emergency, right? Was a romantic crisis an emergency? He thought so. Maybe. He unscrewed the cork cap and took a swig, wrinkling his nose as the liquor slid down his throat.

“Fuck it,” he said quietly to himself.

“Hi, I’m David,” he typed. “I saw your missed connections ad and thought that maybe I was the one you saw in that Tim Horton’s a few weeks ago. My sister and I made a pit stop there on our way to—“ he paused. Maybe specifics weren’t a good idea. He thanked his guardian angel, Meg Ryan, for giving him some sense of self-preservation before backspacing.

“My sister and I made a pit stop there while we were travelling. I was with her in line, so if it was me, then you guessed right about that.” What else could he say? Should he ask for a picture? Or for what the other person looked like? Was he just...supposed to end the email there? And, most importantly, why do the movies make things look so easy? He suddenly wished he were in the middle of all this, not at the beginning. At the beginning, you never really know what you’re about to walk into. But when you’re in the middle of it, you’ve worked yourself into a groove. There’s never anything scary about the familiar. “I like to start my notes to you as if we’re already friends,” Meg Ryan’s character Kathleen had written. But they had already been talking in the movie, David reasoned with himself. He took a deep breath. How about—

“If you want to talk for hours, I can do that. I’m especially good at discussing photography, New York restaurants, and Mariah Carey’s discography at length. Talk soon, maybe.

Until then,

David.”

He hoped the sender would appreciate the call back to their own ad. Before he talked himself out of it again, David filled in the subject line (“Re: Your Missed Connection”) hit send. He cringed as the email sent sound played, but he put the cork cap back on the vodka, slid it under his bed, and settled back into the pillows. He tossed his phone onto the nightstand carelessly. Maybe his phone would shatter into a million pieces and he’d never have to think about that person responding ever again.

“Shut up, David,” Alexis hissed, half-asleep.

You shut up,” he grumbled back quietly. He closed his eyes and settled into a fitful sleep.

The light slanted through the blinds and splashed across David’s face, forcing him awake. He groaned and rolled over to check the time on his phone. 9:54, said the screen. He sighed and rolled onto his back to stare at the ceiling and contemplated starting his day. David was thinking about the endless stretch of hours that lay ahead of him, bare of anything to do, when his phone chimed that he’d received an email. Suddenly he remembered last night: the ad, the vodka, the email he sent. He bared his teeth at the craggy once-white motel ceiling, mentally flinching at what awaited him.

He rolled over to grab his phone and, accepting his fate, went straight for the email app. There, at the top of his inbox, sat a message from [email protected]. “Re: Re: Your Missed Connection,” read the subject line.

David’s mouth pressed itself into a hard line. He chanced a glance over at Alexis’s bed and was relieved to find that it was empty, the sheets thrown back over themselves and the pillows mussed. The bathroom door was open, displaying their dingy, Alexis-less restroom, so David figured she must still be on her morning run. He didn’t know how early she’d gotten up, but figured he didn’t have much time before she returned. He really didn’t want to have to explain what he was doing on his phone.

After a deep breath, he opened the email.

Hi, David,

I’m sorry to say I’ve never been to New York and I’ve only listened to a couple of Mariah Carey’s songs. But I like photography a lot! When I was in college, I used to take photos for the school paper. Gave me an excuse to use the camera my parents got me, plus it made for a good hobby. I was a business major so I didn’t get a lot of opportunities to really be creative. It was a nice outlet. I haven’t picked up my camera in a while, though. Are you a photographer, too? Also, for curiosity’s sake: what are your favourite restaurants in New York and why?

Until next time,

Patrick.

David read through the email a few times. Patrick didn’t seem to be that concerned about whether or not David was actually the person he’d seen. Maybe, David thought, Patrick was like him. Just looking for companionship, sending out missives into the void and hoping someone with a good heart would answer back. David could be that. Whatever this could be, and whoever Patrick was, maybe it could be the start of something good. Something that David could hang onto.

So he smiled ruefully down at his phone and typed out a reply.

Hi Patrick,

I’m not a photographer, but I used to own a gallery. I like to think that means I have good taste, but I recently had to move to a podunk town out in the country and I’m worried that it’s corroded my judgment in art. I don’t own a camera anymore, and even if I did, there’s not much to photograph out here, anyway. Do you think prolonged exposure to tacky old wallpaper and townspeople who think “dressing up” means wearing a polo shirt could ruin my taste? Actually, my taste aside, prolonged exposure to those things may be lethal for me. Jury’s still out on that, though.

To satisfy your curiosity: Sarabeth’s on the Upper East Side makes a braised short rib hash that I still dream about, Bubby’s in TriBeCa has the best pancakes in Manhattan (can you tell I like breakfast food?), and there are very, very few things I would venture out into Brooklyn for, and the pizza at Sal’s is one of them. If you ever find yourself in New York, those are definitely places to visit.

I can’t relate to your major, since I went to an art school in Austria for college and majored in “Creative Processes,” which, previous statements I’ve made aside, is definitely not as practical and high-demand as business. I’m not saying I have the stomach for it, but. You know. It’s important, so.

Until next time,

David

David had just hit Send when Alexis burst through the door clad in her workout gear. David’s head snapped up to watch her pad into the room. How all her makeup hadn’t smudged off during her run, David would never understand.

Alexis popped into their parents’ room for a second and walked back in with bottled water from the mini-fridge. She took a look sip and, for the first time since she got home, finally acknowledged David.

She raised her eyebrows and nodded in the direction of his phone. “So, have you emailed Mr. Missed Connections yet? Or am I going to have to do it for you, like when you made me set up Raya and were too afraid to message Patrick Schwarzenegger when you matched?”

David groaned. “First of all, we said you’d never bring that up again. Second of all, how the fuck was I supposed to react when the son of the fucking Terminator turned out to be interested in men? It was like when Lance Bass came out to you at that New Year’s Eve party. Like, what was I supposed to do with that information?”

Alexis made a face at him. “Ew, David, you’ve seen Terminator?”

“Whatever, I was high at someone’s house and it was playing. That’s not the point,” David said with an eyeroll and a great flourish of his hands.

Alexis sat at the foot of her unmade bed. “You’re right, David, the point is you need to email Mr. Craigslist before I do it for you and, like, say something super embarrassing about you.”

“Okay, how do you know it’s a Mr. though?” David said, wrinkling his nose at her in indignance.

Alexis’s eyes were wide as plates. “Why, is it a Ms.? Have you emailed them?” she asked, getting up and stepping slowly toward him like a leopard on the hunt.

David leaned back against his pillows. “Um. No? But it wouldn’t be any of your business if I did, so,” he said, averting his eyes.

David! You totally emailed them! Let me see what you said!” Alexis squealed, lunging at her brother.

“Over my dead body!” David yelled, launching himself backwards to evade her clutches. He fell off the other side of his bed and scrambled clumsily to his feet. Alexis ended up draped diagonally across David’s twin bed, her legs hanging off one side and her arms stretched out. David tried to make a run for it, but she snagged the cuff of his joggers and brought him down. She kept a vice-like grip on his ankle as she climbed over him and sat down on the small of his back, ignoring his wails of indignance.

“Get the fuck off me, you fucking animal!” he yelled.

“Not until you give me the phone, David!” she said, struggling to keep him on his stomach while she leaned over to reach for his phone.

The door to their parents room burst open and a flurry of feathers and sequins walked into the room. “Children, please,” Moira said with her hand poised at her temple. “Mummy’s reading over some council documents before the meeting today and I need some quiet, so for the love of god, could you take your horseplay somewhere else this morning? In the woods behind the motel, perhaps? It would be a much more suitable setting for this violent rough-housing.”

David paused his frustrated writhing to listen to his mother and Alexis took the opportunity to snatch the phone out of his hand. She hopped up off his back and ran to the bathroom, slamming the door behind her and locking it. Moira, seeing that she’d gotten at least one child to quiet down, threw her hands up and returned to her room. David scampered over to the bathroom door and jiggled the knob.

“Let me in!”

“Ooooh, David, he’s a business major! He’s probably, like, super smart and makes really good money,” Alexis said through the door.

“Alexis, I swear to god, I’m gonna rip your fucking hair out,” David said through gritted teeth.

“Chill out, David! Oh, he sounds so cute! Like a little button!”

“Alexis, give me my fucking phone back,” David seethed.

She unlocked the door and pulled it open, and David stumbled right into her.

“Oh my god, what did you do?” he asked, frantically going back through his sent emails after she pushed his phone into his chest.

She plopped down onto the seat at the table and started twirling her hair around her finger. “I didn’t do anything. This is, like, really cute for you, David,” she said seriously.

He made a face at her that he hoped would mask the pleasant warmth of validation that he felt in his stomach.

“Mmkay, well, I’m gonna handle this on my own from now on. So keep your hands off my fucking phone.”

“Whatever. Just don’t screw this up,” Alexis replied, her pointer finger tapping at the table for emphasis.

David considered her words and bit his bottom lip. He wouldn’t screw this up...right? How hard would it be to keep an email chain going?