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Cherrisnake lover here! Can we see what a first date might be like for them?

I am certain that by this ask, you did not mean "Modern AU where Emily pays for their whole date because she's sick of seeing them dance around each other for years and they go see Hamilton".

Alas, I cannot control myself.

Contains swearing, queerphobia (specifically transphobia), slander of religion, people using religion as an excuse to discriminate and possible implications of child abuse and anxiety.

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Pentious’s hands were shaking as he stood at Cherri’s apartment door, trying to work up the courage to knock. I’m still five minutes early, he told himself. I’ve got time. He clutched the bag with two priceless tickets to Hamilton inside, reminding himself that Cherri had agreed to this and he had planned it to perfection and really, what’s the worst that could happen? Hmm, I don’t know. I could be humiliated forever and cry myself to sleep for the next month.

Cherri doesn’t like cowards. She’s into bravery and all that. I’m only lowering my chances by hiding out here.

Pentious lightly banged his fist against Cherri’s door and waited for a few seconds that felt like eternity.

The door clicked open and Cherri stood in front of him, lightly smirking. Don’t blush don’t blush don’t- Goddamnit, he could feel the blood rush to his cheeks. After some awkward silence, Pentious uncovered in himself the otherworldly determination it took to whisper, “Hi.”

He cursed himself.

“I mean, um- hello!” he blurted. Stop stop stop code red you are actively making this worse-

“Hello to you too,” Cherri responded, a sarcastic but kind smile stretching across her face. She grabbed Pentious by the arm and dragged him into her apartment. He fumbled in his bag for the tickets and handed one to Cherri.

“H-here,” he stammered. “Please don’t think this is, like… too much for a first date… Emily gave me the tickets so…” Jesus Christ, Pentious what are you thinking don’t tell her that!!!

“Are you kidding me?? You know I love musicals, don’t apologize… But you will be sitting through my terrible Angelica impression on the way back so… just wanted to warn you.” Cherri smirked again.

Pentious smiled. “I am well known in my friend group for my horrid George Washington voice.”

Cherri nodded and turned her back to remove her coat from the hook it sat on. “Hm, well I must say I find horrid George Washington voices very sexy.” Before Pentious could respond to that, she held up a finger and hissed, “I said what I said.”

Cherri and Pentious walked to the subway station and after a twenty-minute wait due to some hold-up, collapsed into the comfortable train seats.

Pentious reached in his pocket for the cards he had prepared. The first read, in last night’s tired, drunk scrawling ASK HER FAVORITE COLOR.

He obeyed himself, turned to Cherri, and asked, “What’s your favorite color?” 

“Red, you know, like blood,” she said absentmindedly. “Why?”

“Oh, um no reason, just, you know, get to you know shit and all that, even though I mean, like, we've been friends for years, I should probably know your… OH FUCK! I mean, dammit! Um- Sorry for swearing… There are little children here… fuck it…”

“You’re capable of swearing?” Cherri asked incredulously. “You seem so… innocent… like one of those people who apologizes for saying, like, heck.”

“Um… it’s something that I accidentally do whenever I’m nervous- I try to work on it but often fail, and you’re referring to Emily, not me.”

“Don’t remind me…”

“Of the time she basically got on her knees and begged forgiveness for saying gosh?”

“Blame her upbringing,” Cherri scoffed. “And Sera. And the church.”

“Mostly the church,” Pentious agreed.

“A-hem,” a brunette woman coughed from across the train. She stood up and began to march over towards Cherri and Pentious. “I will not hear the good god-fearing community slandered in the vicinity of my young, impressionable children. And I will certainly not tolerate that propaganda pinned to your shirt, ma’am.” She pointed to the transgender flag and he/him pins on Pentious’s shirt, clearly taking a look at his visible hips.

Cherri stood up. “Hello, what are your name and pronouns?” she asked, a fake-sweet smile on her face.

“I have very strong words to say to you, but unlike you young miscreants, I won’t allow them to taint my mouth,” she said.

A second woman, this one in a leather jacket, left the herd of children the brunette had been ushering on the train and stepped next to her. “Sis, we both know your mouth is already tainted. And if you can’t stand these people insulting your ‘good community’ in front of your impressionable children, why don’t you go spend some time with those children, instead of just insulting their clothing like you have all night?”

The brunette turned to leave, but before she did so, she eyed Cherri, Pentious and her sister, and told them, “You should ask God for forgiveness.”

She turned on her heel and stalked off.

“I am so sorry,” the woman in leather said. “She was completely out of line.” “Please make sure she doesn’t rub off on those kids too much,” Cherri told her at the same time Pentious said, “Forget about us, just worry about those poor children.” The woman smiled. “You too are such a cute couple- don’t worry; I’m not making some stupid ‘people of opposite genders in public- ooh, they must be dating’ assumption. You’re just obviously compatible!”

“Oh, um, well-” Pentious blushed. Again. Fuck.

“It’s just our first date,” Cherri finished.

“I see,” the woman in leather said, nodding. She removed a small notebook and pen from her pocket, ripped out a page and scribbled something on it.

She handed it to them and smiled. “Here’s my number. Call me when you get engaged so I can show up at your wedding.” “Our what?” Cherri demanded. The woman just smiled and left.

After their stop was called, Cherri and Pentious looked at each other, simultaneously shrugged and just laughed.

Suddenly, Pentious gasped. “We’re going to be late, we need to fucking run!”

“Okay, then let’s run!” Cherri yelled, grabbing Pentious by the wrist again and basically dragging them out of the station.

Once they’d finally made it to the theater and dodged death a few times, Pentious was gasping and Cherri was barely breaking a sweat.

“How… are you… so fast?” he demanded between breaths.

“I did cross-country in high school. Come on, we can’t miss anything!!” she yelled.

Finally, they managed to make it to the theater and settled into their seats. Somewhere between “The Schuyler Sisters” and “Right Hand Man”, Cherri and Pentious’s hands found each other.

After the show, Cherri and Pentious bought pretty much their weight in Hamilton merch (Emily was sponsoring their whole date, anyway, what did it matter?) and called an Uber- they were not in the mood for another wonderful subway experience.

Waiting in the dark, they talked about a lot of things they just hadn’t had time to discuss before, smiled, laughed, and got a little emotional.

Their Uber arrived and dropped Cherri off at her house, then drove Pentious the rest of the way to his.

The next morning, Pentious’s phone lit up with one text from Cherri: So, what flavor cake should we have? Wouldn’t want to let the cool aunt down.