This is made for  LittleHamiltonElams!!! Hope this is close to what you wanted!

*Also, I thought this pic was pretty perfect, just pretend its modern :) *

Alexander Hamilton has met Elizabeth Schuyler before. She was best friends with Theodosia Prevost, who was dating his friend Aaron Burr, she was sisters with Peggy Schuyler, who was kinda sorta dating his best friend John Laurens, and she was also sisters with Angelica Schuyler, who was dating his friend Lafayette.

Then there was just Alexander and Elizabeth without someone to date

Well, Hercules Mulligan too, but we don't talk about that

Alex decided to take a shot on Eliza

Alex made his way to the café on Washington Ave. He knew Eliza worked there, and it was about the time of her break. He walked in as she was grabbing her coat

Alex felt so confident before.

And now he feels like when a grandparent is telling you an hours long story, and you don't know how to leave.

"Heyyyy Elizaaaa" he said in an uneasy voice

'Oh! Um, hey Alex. What are you doing here?" she asked as her face brightened up

"Well, I was, umm, ah, wondering if maaaaaaybeee you would... ya know... go out with me for your break?" Alex said, and gave a mental MAJOR facepalm

"Um, okay! Just let me grab my things!" she exclaimed, and ran towards the back

The truth was, Eliza had all her stuff in her hands

She just went in the back to sqeal

She then came back out and her and Alex walked out

***

"Wow, that was really good!" Eliza exclaimed, finishing her taco salad

"I know, riiiiiighttt?!" Alex answered, biting of the last bits that had broken off of his hard taco shell.

He then dropped his keys. He bent down to get them, and then as he picked his head up, he hit his head hard on the table. He was startled, and he ended up falling out of his seat completely. Alex screamed

Eliza snorted and covered her mouth as she tried not to laugh

"Hey! It wasn't that  funny!" Alex laughed as his face came back into view

"Yes, yes it was" Eliza giggled

"Hey, um, E-Elizaaaaa?" Alex asked, stretching out the 'a'

"Y-yeah?" Eliza questioned, smiling. Boy, she was helpless!

"Would you, I dunno, maybe wanna, ya know, g-go out with m-me sometimeeee?" Alex stuttered

"Of course! When?!" Eliza answered, hyper

"Um, t-tomorrow at like, 6?" Alex asked, his hands becoming sweaty

"Great! Pick me up!" Eliza said as they got to the outside of her job

"B-bye, Eliza!" Alex said, awkwardly smiling

"Bye Alex!" Eliza exclaimed, and walked towards the door

'Woah! I think I did amazing!!!' Alex thought, smiling.

"Hey Alex?" he heard. He saw Eliza still standing by the door

"Uh, yeah?" Alex asked, all his confidence gone

"Just, wow, your really bad at flirting, Alex " she said, and then she was inside

Alex smiled like a goof and walked off

And Eliza was inside, ranting to her friend Maria.

I guess they both really helpless!