Pity Party Tales: The $50,000 Wager

I had been sitting in the tiny coffee shop for hours, nervously sipping decaf while watching the door.

“Anything else I can get for you, dear?” asked the shop’s owner, an elderly woman in a yellow smock with oversized glasses.

“I’m fine,” I replied.

She nodded and returned to her solitary duties behind the counter. It was only the two of us in the shop, and it had been that way for some time. I was starting to worry that Ian had been wrong—or worse, that he was screwing with me.

Then, the doors burst open, and my senses were overwhelmed:

I heard the sweet melody of the door chimes, felt the warmth of the summer sunlight flooding into the cold café, and finally, I saw the most beautiful woman in the world.

Ian was right.

Okay, relax, I told myself.

She walked toward the counter, and I glued my eyes to my cup. I heard her order a black iced coffee. I heard the owner pouring the drink.

I reminded myself how important the first impression would be. I knew the next few minutes represented my best chance at blowing this.

Just breathe.

I heard her thank the owner.

I heard her sip from the straw.

I heard her walk toward me…

“Excuse me,” she said. “This is going to sound silly, but you’re kind of sitting at my table.”

I turned—not too quickly, but not too slowly. I made a friendly smile, the kind I might give an aunt, and replied, “Well, I’m leaving in a minute, but you’re welcome to sit with me till then.”

She put the straw to her lips, taking a thoughtful sip before replying, “Sure.”

The table was circular and small, with two high stools. She sat across from me, pulling the stool out slightly so our legs wouldn’t touch under the table.

“I’m Max Davis,” I said casually, not extending a hand.

She smiled. “I’m Anna Parker.”

One Year Earlier

In order for you to understand what I was doing in that coffee shop, I have to take you back to the day Ellie broke up with me. We had been together for four months, and I thought things were great. Then she texted me those four gut-wrenching words: We need to talk.

Ugh.

She told me we were in different places—that she wasn’t ready for the type of commitment I clearly wanted.

“I don’t understand,” I said, holding back the waterworks. “I thought you wanted to get married?”

Her lips pursed. “I do… one day…” I could read between the lines.

“But not to me.”

She exhaled sharply, then said, “Right. I’m sorry, Max.”

We hugged.

She left.

I cried.

And that was that—four months up in smoke.

I sent a message to the group chat with my friends:

Me: Ellie broke it off ):

Kara: Srry bud.

Ian: Pity party?

Mikey: I’ll grab some beer.

Me: No, guys. I’m fine.

Ian: Pity party!

Kara: I’m in.

Me: No… don’t come over. I just want to be alone.

Ian: Ok.

Me: Thank you.

Ian: Be over in 15.

And he was—Kara and Mikey following soon after.

With my three friends in tow, my one-bedroom apartment was at full capacity. I had wanted to stew in my misery, but after a few beers I felt glad they’d forced their way over.

Ian raised his can. “To hoping this will be the last pity party!”

The pity party was a tradition Ian started a few years back after my first truly devastating breakup. I had dated the girl all four years of college—only to be dumped four months after graduation.

Feeling bad, Ian paid for the four of us to spend the weekend in Atlantic City.

I should probably mention that Ian is insanely wealthy. He invented some cloud-based software—whose actual use, ironically, goes over my head—and sold it to Microsoft.

He’s in his twenties and basically retired. You might think getting that rich so young would change a person, but he’s basically the same guy I grew up with.

It’s fun being friends with someone that wealthy—especially someone who isn’t shy about sharing with his pals.

A few minutes later, Kara grabbed the remote.

“Yes, you can use my TV,” I snarked.

She was already turning it on. “I have to see what happens on The Company,” she replied.

Kara had been my friend longer than anyone—our families lived two houses apart. Growing up, people often mistook us for siblings.

Made sense to me.

We’re both on the taller side with bright green eyes and chin dimples. I used to wonder if we actually were siblings—if our parents had had an affair. I think that’s why I was never into her.

“You seriously watching that show?” Mikey asked.

“Um, yes,” she replied sharply. “What’s your problem?”

Mikey fiddled with the rim of his Mets cap, then said, “No problem. I just wonder why someone would watch that when they could watch literally anything else.”

Kara punched his arm, then pointed at the woman on the TV. “I’m surprised you wouldn’t watch it for her.”

Mikey scoffed. “What kind of Neanderthal do you take me for?”

Ian jumped in. “The Mikey kind.”

It was true—Mikey loved sharing the weird ideas his libido bestowed upon him.

Grinning, Mikey said, “It’s the year 2024. I don’t have to watch this show to see pictures of Anna Parker.”

Yup—that Anna Parker. The one from the coffee shop a year from now. But shush, I don’t know about that yet.

I glanced at the screen, then said, “That’s the girl everyone is losing their minds over?”

I don’t watch a ton of TV, but I see people post about Anna Parker online all the time.

“You don’t think she’s pretty?” Kara asked.

“I wouldn’t say that,” I replied. “She’s fine. She’s just kinda…”

“Kinda what?” Mikey prodded.

“Normal looking…” I said, my inflection somewhere between a question and a statement.

“You have to watch more of her stuff,” Mikey insisted. “Then you’ll get it.”

“I think Ellie was prettier,” I said—breaking the number one rule of a pity party.

Ian thumped me on the head with a cushion. “Foul! No discussing she-who-must-not-be-named.”

“Right, I know.”

A few minutes passed, and I thought the topic of Anna Parker had died, but Mikey had other plans.

“You know, she’s single,” he said.

“Who?”

“Anna Parker!”

“Oh, right,” Kara perked up. “She just got dumped.”

“Just like you!” Mikey said, patting my shoulder.

I shook my head, knowing better than to clap back at Mikey. Unfortunately, he wasn’t done.

“What if you went out with her?”

Kara burst into laughter.

“What’s so funny?” I asked, though I understood exactly why it was ridiculous.

“She’s a famous actress,” Kara said.

“So… actresses date normal people all the time.”

“Okay, sorry,” Kara said—without even trying to sound sincere.

Ian had a look on his face that I didn’t like. It was the same look he’d had before he proposed we spend the summer hiking the 46 peaks of the Adirondacks.

“What if you did try to do it?” he said.

“Do what?”

“Date Anna Parker.”

“You can’t be serious…”

“Why not? It’s like you said—she’s normal looking—”

“Yes… but—”

“And actresses date normal people all the time.”

I was all for joking around, but the seriousness in Ian’s voice had me off balance. It was outrageous to imagine myself pursuing someone like Anna Parker. For starters—

“How would I even meet her? It’s not like she’s on Hinge.”

“What if I could set that up somehow?”

Ian knew people in high places, but the notion that he could arrange a meeting with someone who had an Emmy was far-fetched.

“Sure,” I said, placating him. “If you can set that up, I’ll do it.”

Ian stood, snatched the remote from Kara, and paused the TV. “Let’s make it interesting,” he said over Kara’s shouts of dismay. “If you get her to agree to go on a date with you, I’ll give you $50,000.”

“WOAH!” Mikey said, jumping off the couch. “Is that offer good for anyone?”

“Nope, just Max.”

Mikey slumped down, pouting.

Ian consoled him. “We can’t have you guys competing. We’re gonna need all hands on deck.”

Mikey chewed on those words, then nodded. “Good point.”

Kara cackled. “Yup, with Mikey out of the way, this is a lock.” She fell out of her seat, laughing so hard.

“Well,” I said, “Kara’s on board.”

At some point, we agreed that I would have a year to make this happen—contingent on Ian orchestrating a meeting.

Which I found as likely as Mikey eating a piece of broccoli.

For context: Mikey hates broccoli.

So I went on with my life, doing my best not to think about Ellie.

I showed up to my boring office job (the details of which I will not torment you with). I was minding my own boring business when I heard a coworker—who I nicknamed Generic-White-Male—saying, “Did you know Anna Parker has a house upstate?”

Generic-White-Male #2 replied, “That’s cool. I love her on that show… what’s it called… The Industry?”

GWM #1: “Oh, she’s in shows?”

I raised the volume on my headphones, opting out of the riveting conversation.

Later, I caught another coworker watching a clip of Parker on his computer. I overheard two women complaining that their boyfriends were obsessed with her.

Way to pass the Bechdel test, ladies.

No matter where I looked, I found Anna Parker. The logical side of me knew it was a coincidence, but the other side wondered if it was a sign…

Back at home, I redownloaded the dating apps and spent more time than I’d like to admit swiping. I still wasn’t taking this Anna Parker thing seriously, but I wasn’t thinking about Ellie too much—and that felt like a win.

The next morning, I had a dozen matches, and I messaged them all, figuring I might as well dive back in headfirst. By lunch, I had two dates scheduled for the weekend.

While meeting new people was undeniably exciting, it came with a side of existential dread. Every failed relationship felt like an indictment on the next—as if I were building a file that every woman could see, with every ex adding to it:

He’s too clingy.

He was way too into me too soon.

He never gave me any space.

Well, it only had to happen once. Maybe one of these two girls would be the one. The only way to find out was to try—

My phone buzzed in the midst of my internal pep talk. I had a message from Ian:

I figured out a way to make it happen. I’ll come over tonight to discuss.

That message swallowed my day like a blackhole.

Could Ian have actually set up a meeting between me and Anna Parker?

The answer was: sort of.

The whole gang came over for Ian’s announcement.

“I heard from a reliable guy in the industry that Anna Parker vacations at a place upstate for three weeks during August,” he said.

“So?” I replied curtly. I wasn’t about to stake out her house.

“Let me finish,” Ian said. “My source told me she visits a tiny coffee shop every day around noon—and always sits at the same table.”

I wanted to say so what? but instead I tried, “And how does that help me?”

Mikey jumped in. “You have to wait at the shop for her.”

I chuckled, assuming he was wrong.

But Ian said, “Exactly! It’s the perfect setup.”

“I don’t know…” It felt a little close to stalking for my tastes.

Kara, who had been snickering to herself, said, “It’s as good a shot as you’re gonna get.” Then she burst into another fit of laughter.

I chewed on the idea. I pictured myself sitting alone, waiting for her to show. It was creepy, sure—but people meet in all sorts of strange ways. Plus, I really wanted to prove Kara wrong.

I imagined the stunned look on her face when she found out I was dating Anna Parker. I imagined introducing her to people as my girlfriend. And I imagined my exes reading about it online. That last one sealed it.

“Okay,” I said. “I’m in.”

“Yes!” Ian said, grinning. He glanced at Mikey. “Should we start his training now?”

I didn’t like the sound of that.

Mikey nodded. “We’re going to need all the time we can get.”

They spent the next three hours telling me everything they knew about Anna.

Side note: I decided that since I was going to pursue her, I was going to think of her as Anna, not Anna Parker.

I was shocked by how much they knew—Mikey listed her roles like he was her IMDb page. Kara told me about Anna’s old boyfriends—most of them actors.

By the time they left, I felt like I’d been beaten over the head with her biography.

I canceled my dates.

I deleted the apps.

If I was going to do this, I was going to do it right.

I spent my nights watching Anna’s movies and shows. I downloaded every podcast she’d ever been on, watched every interview she’d ever given.

My friends helped me prepare.

Mikey came up with the idea that I should pretend not to know who she was. “She probably gets hit on by creepy fans all the time.”

Kara gave me a Brandon Sanderson book the size of a mini-fridge. “He’s her favorite author,” she told me.

Time melted away as my friends kept coaching me. By the time August finally arrived, I was convinced nobody knew Anna better than me. I was also convinced I could make her happy.

It was Mikey who told me that first impressions are formed in the first thirty seconds—and that I couldn’t appear too eager to talk to her. “Play it cool,” were his exact words.

I knew he was right. It was the same thing I’d heard from countless girls—and by “countless,” I mean six.

To make it work with Anna, I had to be different. I had to take what I learned from the girls who’d broken my heart and become the guy they’d wanted me to be.

So now, we’re back at the coffee shop.

Anna was sitting across from me, sipping her iced coffee.

This was it.

Don’t blow it. Don’t be too eager.

I avoided making eye contact with her, while clamping down on the word vomit that desperately wanted to escape my mouth.

It was painful—every instinct in me was screaming to talk.

I couldn’t take it anymore; I was about to crack when, amazingly, she broke the silence.

“You’re reading The Way of Kings?” She pointed at the overgrown book Kara had given me.

I nodded. “Yup.”

“How do you like it?” She sounded thrilled to have someone to discuss the book with.

“It’s okay,” I said, playing it cool—not being, as Sophia had called me, “too much.”

“What part are you on?”

I glanced at her. “I just started.” Then I looked back at my drink—I worried I’d turn beet red if I looked at her any longer.

“Well, I hope you like it,” she said.

“Thanks—”

Wait…

She pushed her chair in. “I think I’m gonna take this to go. It was nice meeting you, Mike.”

Panic exploded within me. My mind raced—running through a million different things I could say to get her to stay:

You have a Goldendoodle, right? I had one growing up!

Dinner later?

I thought you were great in The Monster Mob Movie.

Plans for food?

They shouldn’t have cancelled The Company.

Date with me?

Anna, I love you!

Anna, don’t go!

What I actually said was, “It’s Max…”

“Oh,” she replied, already at the door. “Bye, Max.” Then she was gone.

One Day Later

Kara couldn’t stop laughing about how everything went down.

Mikey was teasing me for actually listening to him.

And Ian was sipping cheap beer from a golden mug.

“What?” he said as we stared at the extravagant glass. “I had an extra fifty grand to spend.”

I laughed so hard my stomach hurt. To be honest, I had forgotten about the money…

Ian grinned, raised his glass, and said,

“To hoping this will be the last pity party we ever have!”