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3 times Angelica Schuyler broke a heart, and the 1 time she got her heart broken

Summary: Thomas Jefferson, John Church, and her own father. Angelica Schuyler could make many people regret their decisions, make many people curse their hearts for falling for a person like her. She never thought that she could feel so many things, that she could hate her heart, that treacherous being, as she did when she met Alexander Hamilton.

Thomas Jefferson

From the moment Angelica walked into his life, he had had feelings for her. From their first meeting in kindergarten to that last goodbye in his apartment, they had been fast friends. From their first meeting, they had shared so many important milestones and memories that it was difficult to discern which ones were simply figments of their overactive imaginations.

It became quickly apparent that Thomas was one of the only people who could match Angelica in a battle of wits, or intelligence. It only served to help spur their achievements, both people driving and competing against each other, providing marks on the wall for them to constantly cross.

They were best friends straight from Kindergarten through to freshman year, but even the strongest bonds frayed eventually.

However, the first time Thomas truly noticed Angelica Schuyler was during debate club, in Freshman year. He noticed the way her long wavy hair hung just past her shoulder blades, swaying gently as she strode the hallways with confidence. He noticed the way her eyes sparkled with intelligence. He noticed her words, the way she could weave them seamlessly into pictures, entrancing almost everyone listening. Once he noticed himself noticing these details, he knew he was gone.

It was a normal day, and normal things were happening as they usually would.

'Hello everyone, and welcome to the first session of debate club for the semester!' The general greeted to the classroom.

'For a demonstration to those who are new here,' he continued, with a meaningful glance towards James Madison, Alexander Hamilton, and John Laurens,

'Let's show them a taste of Revolutionary debating! Thomas, Angelica, why don't you start us off?'

Washington asked his top students, and the class, all of which was currently hosting a small riot,

'Also, although I do understand how exciting this must be, it would be nice if everyone would quiet down,' he asked after, as the friends made their way up together, competitive smiles mirroring the other on their faces.

'The topic is women's rights, Angelica for, Thomas against,' Washington said, still hosting a grin as he sat back down to let his students get to work.

When Angelica destroyed him that afternoon, and for the first, he didn't care. The only thing he saw at that moment was the way her eyes sparkled with the victory, the way she seemed bouncy for the rest of the period.

The next day

'I am so sorry, Thomas, but even you can tell we didn't really mean to get so tangled up, right?' Angelica asked with a small smile as she gestured to the predicament she had found herself in (Thomas's apartment). Thomas nodded numbly, the weight of his actions not occurring to him as she left the room without another word. When she left, all Thomas could think to do was heave out the long, heavy breath that he had been holding in. All he could do was sit there and stare at the empty space his best friend and longtime crush had just vacated. She had walked out of his life as easily as she had walked up to him and declared their friendship all those years ago. He could have sat there all day, silently reliving once warm memories, memories that now haunted him like sentient beings, beings with sharp minds of their own.

He did too, until James Madison, his friend for as long as he could remember, burst through the door, carrying chocolates and french pastries. James set the treats down of his coffee table immediately, surveying the scene before him. Before Thomas could really do much, his best friend was on the floor beside him (since when had he been sitting on the floor?).

'I'm sorry,' was all he said. For the first time, in what, 30 minutes (?) Thomas broke his intense stare with the wall. He leaned into James' embrace, finally letting the tears that had long ago been clouding his vision fall.

'I really thought i might have been able to make that work, y'know?' he asked, in a thick voice that he never thought he could own.

'Yeah, but hey, at least your not the only one whose heart got broken by her, huh?' James asked, cracking a small smile.

John Church

John smiled as he walked his girlfriend of 4 years now to their favourite spot in the city. The hollowed out tree next to where the had first met had been a near sacred spot for the both of them, and he hoped that it would be the host to many fond memories they would look back on in a few years time.

He revelled in the quietness, away from their constantly moving lives, what with her life as a lawyer, and his profession in the military, they weren't quite the normal pair.

Angelica exclaimed quietly when she recognised the spot he was leading her to.

'Wow! I had almost forgotten this place!' she said quietly, careful not to disturb the delicately peaceful atmosphere around them. She didn't notice the way Church's shoulders slumped along with her offhand remark.

John took her hands and carefully helped her onto the branches of the hollowed out oak tree, one that held so many fond memories for the both of them.

'What are we doing here?'' Angelica asked, her confusion evident by her furrowed eyebrows.

'So you know how we have so many memories about this place,' John started out hesitantly, butterflies of worry and anticipation flying around his stomach,

'I think it's time to make a new one,' he said, bending down on one knee. Angelica looked at him in utter shock, and he felt a twinge of satisfaction, he had managed to finally get her speechless.

'Angelica, I've loved you for more time than you could imagine, so please, will you marry me?' he asked after a deep breath, holding out a little black box. Angelica simply looked at him, her face screwed in a mixture of horror and excitement. He was starting to get really nervous.

'Angelica?'

There was no answer. He knew he had screwed up. All he heard was a small mutter, before she ran away, presumably never to see him again.

'Oh shit….' he muttered softly, looking around at the hollowed out tree, which was starting to feel claustrophobic and closed in without another human with him.

John Church fled the hollow, he didn't look back. The only memory he could now remember was the feeling of hot, wet tears blinding his eyesight as he ran back to his dorm, determined to forget the evening had ever occurred; determined to wake up and find it had all been a nightmare.

There was so much that had been going to happen, there was still so much that they hadn't done.

Philip Schuyler

Philip Schuyler knew from the first time he set his eyes on his firstborn child that she would do great things. She had large, doe eyes strikingly similar to her mother's, and sharp, angular features distinguishable from birth. Even in the matron bed of the hospital, she was a quiet baby, looking around at her surroundings in an awestruck wonder. He could only hope that his little girl would retain that innocence throughout her life.

He didn't realise then how his daughter would fail to walk along the path he had so carefully set before her. How she would create her own, spitting in his face the work he had put into making her life something out of a fairy tail before she was even born.

He failed to realise how she wouldn't stand for being the kind of women needed in the aristocratic world she born into. The world that still followed morals left behind by other long ago. That she would want to do something, that she would want to be someone. He failed to realise that she wouldn't survive well in the life he had crafted for her, that she wouldn't take well to a pre decided destiny.

He was ignorant of the fact that she might not need the type of daughter he needed. That, hard as she might try, she would never impress him, never induce the kind of burning pride all parents were meant to feel when their child succeeds a goal.

Still, it was sweet while it lasted. Philip smiled softly, tears dripping down his cheeks as he held his firstborn near his chest, feeling protectiveness wash over him. He knew this one would do great things, and he would try as he knew how to encourage her. He promised to love her unconditionally, through thick and thin, on whatever path she chose to follow.

On his deathbed, he wished he had kept that one promise; the one promise he failed to keep.

One time she got her heart broken: Alexander Hamilton

Angelica Schuyler had lived, loved and lost just like all other human beings. She had thought it might have been different with this one. Instead, it had ended before it even began. She first saw him - really saw him when they were paired together for a group, geography, if she remembered correctly. The first thing she noticed about him was his eyes. The colour of freshly grounded coffee beans, they were full of lively intelligence; they were full of worldly knowledge at the tender age of 16. Unparalleled by all the others she had seen first, it was those eyes she fell in love with first.

Alexander had always managed to charm her family, maybe the first time she had brought a boy home that her father had instantly approved of. From the first time he visited, straight through to when he officially joined the family, he was a welcome addition to the lively household. Her mother, Catherine, fell for his impeccable manners, his delicate, almost feminine charms. Her father, Philip was immediately taken in by his extensive knowledge on American history and early politics; his firm stance behind the Democrats, of which Schuyler was a senator for. Her younger brother Philip loved the fun facts and life hacks Alexander always brought with him. Alex always treated 9-year-old Peggy like an equal, and she basked in his attention. It was her slightly younger sister Eliza's reaction that shattered her heart into little pieces.

From the very first time Eliza saw him, she knew she was helpless. With his shoulder-length, bright red, glossy hair and the lanky, relaxed confidence radiating from every pore in his body, she knew she was gone. Gone and never coming back.

'Yo, this one's mine,' she whispered conspiratorially to her older sister at the first moment she then got Angelica to herself. Her voice was weak in giddy happiness. She didn't notice the fractured light emanating from Angelica's usually bright hazel eyes, as if someone had just shattered her beautiful irises. She didn't notice how her older sister seemed to slump as if the terribly tight, fraying shred of rope had she had been holding onto had just been violently ripped to shreds. All she heard was Angelica's forced smile, and her words of agreement. The words that took the light from Angelica's world, and made Eliza's just that much brighter. Something Angelica would have sacrificed anything, anything to make that happen.

After that, Angelica tried, she really did. She tried not to watch his dark silhouette as he wrote furiously for whatever paper he was working. She tried not to notice the dark swirling patterns in his eyes that had first enraptured her, which she kept finding more of as she cleared away the shadows constantly clouding his eyes. She tried so terribly, terribly hard to distance herself from the sharp mind, sharper tongue and beautiful eyes of the boy that she had loved for so long. She stayed friends, but left it up to her younger sister to invite him to their mansion, and accompany him to parties and dances. She always pushed him away now, pushed him away into Eliza's waiting hands. Alexander might still have been an almost permanent fixture in the Schuyler mansion, but it was no longer because of Angelica.

That didn't mean that she didn't notice how undeniably happy Eliza was when she was in the same room as Alexander. The younger eyes seemed to brighten up and glow with a light she hadn't seen in Eliza's eyes for a time that seemed much too long in the eyes of a doting older sister.

That year, Alexander asked Eliza to the prom. Saying that she was happy for the two of them would be an understatement. She was absolutely elated that her closest sister and one of her best friends had found love. Eliza had found someone to spur her on; she had found a broken soul she could repair, someone who truly, deeply needed her. Alexander had found someone who encouraged him in his endeavours , yet grounded him when he floated too far, working himself half to death and not looking back.

Five years later, Alexander asked Eliza to marry him. As the Maid of Honour, Eliza was counting on her, as she couldn't let that trust down. Still, it was hard when you were talking about the undeniable love her sister, and the one person she had loved for years, shared. Still, it was her duty to her sister, something she out before anything else, and if that meant the only thing she could do was watch from afar, hoping that their love was strong enough to overcome all the challenges life threw at them, then that was what she would do. Because after all, what else did Angelica Schuyler do other than watch from afar, protecting her family?