Hamilton Oneshots!

Problematic (PT. 1) {Phillip x Reader}

this'll be one hella interesting ride

pairing; phillip hamilton x reader

time; modern

warnings; blackmailing

type of oneshot; kinda angsty

requested?; yUp by @0HamiltonUnicorn0 thanks for the request~

they in college btw just thought ya'll should know

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Pip's POV

To say I had a crush was a bit of an understatement. To say I was also the stereotypical flirt was also an understatement... so I had a bit of a conflict. I only flirted with every girl so I could try and forget my own crush; I knew she'd never like me back. I flirted too much. (Y/N) wasn't much of a flirty-liking person.

No one else knew about my crush. At least not until today.

I was currently talking with one of my good friends, Frances Eleanor Laurens. She was my go-to confident when it came to many things (the rest I told Y/N).

"Sooo what's the news this time, Freckles?" Frances asked as we sat down for lunch in the local café.

"It's... about a girl I like..." I started.

Frances feigned shock. "Phillip Hamilton liking a girl?! No way!"

I reached across the table and slapped her arm as she laughed. "Shut up, Fran!"

"Fine fine. Carry on."

"Well you know her. She's a good friend of ours."

"Ooo! Theodosia?"

I chuckled. "No no. Theo's a great gal, don't get me wrong though."

"(Y/N)?"

"Ding ding!"

Frances held in a squeal but I heard a squeak, causing me to laugh. "I knew it, I knew it, I knew it! That's too cuteeee!" (me when I found out my older best friend had a crush)

I shushed her, still laughing. "Do you want to draw attention, Fran?"

She giggled. "Sorry Pips. I'm just excited! She'd so go out with you!"

I shook my head. "I'm such a hardcore flirt! There's no way she would!"

"Phillip Hamilton! For such a flirt, you're so thick-headed," Frances grimaced.

We continued joking and talking about my current situation, and little had I known someone was listening.

Theo's POV

I couldn't even begin to believe my ears! My crush liked my best friend! I loved (Y/N) to pieces... but Phillip! I had a plan, a risky one that would probably cost (Y/N) and I's friendship, but it was a risk I was going to take.

Sorry best friend, I'm sure we'll be back on track in no time. Hopefully...

Back to Pip's POV

~ that night ~

I got back to my dorm after spending the day in classes and with Frances and (Y/N). The two girls had gone off who knows where, though I assumed (Y/N) went back to her and Theo's dorm and Frances went off with her girlfriend. Who knew though.

When I reached my door, I saw a folded note taped to the door, my name in neat writing across the front. Confused, I grabbed it and opened my door, closing it behind me and plopping on my bed.

I unfolded the paper and a smaller piece of paper slipped onto my lap that I quickly identified as a photo. I picked it up, dumbfounded at what I saw.

It was a photo of a time Theo had kissed me. We had been hanging out and she asked if we could take a photo. She set it to a timer and as it counted down she had tapped me, then kissed me. It was an... interesting time. I knew only she had the picture so I went to the note.

'Pips,

You may be a bit weary with the photo, but don't fear! That photo is still between us as of right now.

However, I had a request. I just so happened to overhear you and Frances at the café today. I heard all about your crush on our best friend. That's a shame really. I have a crush on you, and so does she!

If you want that little photo to not only get to (Y/N), but the rest of the college as well, then don't date me. Date me, drop your contact with (Y/N), and the photo will be kept safe. All of it. I don't want to see any texts, any calls.

The choice is yours, Pips. Get to me by tomorrow!

Love,
Theodosia'

I couldn't believe it. No matter what I did, (Y/N) would be hurt regardless. It seemed like a hard choice, and it was, but I figured my best choice was just dating Theodosia. I didn't want to drop all contact with (Y/N), but what else was I to do?

I could only hope it went well...

...