Will the stars ever align?

the pact

PRESENT - DAY ( 2032)

He thought of when she had posed a question that took him aback. "Could you ever find it in yourself to love me?" He hesitated. He took a deep breath, and answered coldly and resolutely, "No. We don't do love. Love is for the weak."
A slight tinge of disappointment was visible in Lisa's eyes but he had chosen to ignore that.

He was rushed back to Times Square as his thoughts were interrupted by his chauffeur. "Mr Sinclair. It's been over an hour that you've been sitting idly waiting for her. I don't think she'll come."
Nate tilted his head ever so fashionably to turn to his custom Jacob&Co 'Billionaire' watch model. It was 9:11pm and Nate realised he had been sitting on the side of the public seating area for over 2 hours now, staring aimlessly - while in deep thought - at all the bright advertisement hoardings all around. And there in the middle of Times Square, on the tallest tower, there it was in its unquestionable beauty. A yellow hoarding with 'Sinclair Pvt Ltd' written in a large blue font. His company had always been everything to him. His father taught him in his childhood that to succeed in business, you must be cold and manipulative. That nothing else mattered. Nathaniel paid heed to his father's teachings. He prioritised himself and his work over everything else and as a result, lost many friends and people from his life. Most significantly, he had lost her. Lisa Blossom. Nate sighed as he breathed heavily against the cold New York night.

He looked around to catch a view of the vibrant pathways around. People bustling around, pushing each other, not seeming to have a care for anything else. Nate always wondered why they chose Times Square to be the place. Wasn't a calm, isolated and scenic spot supposed to be more romantic? "Ah well, we were young then," he thought to himself.
It had happened years ago.
On a midnight call with Lisa at the peak of their high school relationship, the 2 young teenagers had decided to make a pact. A pact that if they were ever in New York City at the same time, they'd go to Times Square at 7pm everyday until they met. "Pinky promise?" Nate asked. She whispered in her soft, beautiful voice, "pinky promise baby." Nathaniel felt chills down his spine as he remembered those fateful nights. Anyways, Lisa was in town. He had inquired around and discovered Lisa was a leading fashion designer at Louis Vuitton. He felt very proud when he found out, that she had been able to accomplish her goals. It was the NYC fashion week, and he was fairly confident that she was in town.

Suddenly realising his chauffeur's presence, Nate looked down at his feet for a moment as he stood up in an unsure pose, suspended between the desire to give up for the night or keep the seat warm a little longer. Ultimately, he decided to stay. He was astounded at how the cold player in him had ever become such a romantic. "Go home for the night, Arnold, back to your wife. I'll stay here." "Are you sure Mr. Sinclair?" Nathaniel nodded and the chauffeur took that as his sign to be dismissed.

These flashbacks of their relationship haunted Nate till date and he sighed. Over the years, he couldn't help but feel regret about certain character traits of his. His cold self didn't allow him to get close to anyone. He pushed people away as he felt it was more of a burden than a gift. No one ever managed to understand him. And consequently, his relationships never worked out. It's why Lisa and Nate had failed. Wait, that wasn't an accurate representation of what had happened. It's why Nate had failed Lisa. But as much as Nate wanted to blame himself for everything that had gone wrong, he knew in the back of his mind that Lisa had never really understood Nathaniel. 
Given the way they had ended stuff, Nate wasn't quite sure if Lisa would keep the promise she had made on that fateful night, all those years ago.

All he had was hope. And he wasn't ready to let go of his grasp on that. Not just yet.