Simon
Ali glanced at herself at her full body mirror and tugged at the hem of her dress for the umpteenth time in the past five minutes. The smooth silk of her dress felt different and weird under her fingertips, just as much as the entire situation she was forced to be on felt. She hated blind dates with a passion, forced pleasantries, the expectations, and the awkwardness. But most of all, she hated the fact that her parents were the one who set this whole thing up in the first place.
“Ali, sweetheart, you’re 29 years old.” Her mother said, her tone tinges with disappointment and urgency at the same time. “You’re not getting any younger.”
She internally scoffed at that. As if she even needed the damn reminder that she was getting older.
Ali let out a breath through her nostrils as she looked around the dimly lit restaurant. The place clearly screamed sophistication and class. The air was filled with hushed conversations from the patrons, the occasional clinks of glasses and silverware, the soft flickers of the candlelights and for some damn reason all of it felt suffocatingly intimate for the stupid date her parents set up for her.
Hell, she didn’t even know the name of the man that she was going out with, all she knew was his career, something that had to do with finance-adjacent. She had to stop listening to her mother gush about the man and how perfect he seemed because in her mother’s eyes perfect meant successful. She wanted to protest some more but she was already too exhausted to deal with what her mother had planned for her. If this one stupid dinner would get her out of the passive aggressive comments her mother made then she would endure the bloody date.
But then she saw him.
Ali stopped mid-step, she felt a painful knot twisting in her stomach. Sitting at the table booked for the date was Simon Caldwell. Her ex’s boss.
This was the last person that she wanted to see, let alone sit across from for an entire meal. Simon was known as someone who was ruthless, intimidating, the kind of person who never wasted words and always expected perfection. She had only met this man a handful of times while she was still dating her ex, Daniel, but each and every encounter and left a lasting impression on her.
Simon had always been the reason why her ex had spent countless nights at the firm and the reason why her ex was always complaining about the relentless pressure to be better, to work harder. Simon was the one that Daniel had resented the most, up until he turned that resentment towards her instead.
Simon looked just as imposing as she had remember. He was dressed in a sharp black suit, his dark hair neatly styled, and his expression barely readable as he scrolled through his phone. Even seated and partially relaxed he exuded power, control, and a presence that commanded attention.
Ali barely managed to force her feet forward, her limbs stiff as she walked. She had to be wrong. There had to be some mistake, but as she hesitantly cleared her throat, Simon looked up, his gaze locking onto hers. For a brief second, something flickered in his sharp blue eyes. Was it surprise or maybe mild recognition? Before she could even decipher it, it disappeared just as quickly as it had come. He arched his brow as he set his phone aside. “Ali.”
Her stomach already twisted in a painful knot, twisted some more in her gut. He remembered her.
She exhaled softly through her nose, “You… You’re my blind date?”
Simon didn’t respond to her, his steady gaze studying her. As if his mind was coming to a conclusion, he let out a soft breath through his mouth, barely perceptible. “I take it that you didn’t know.”
“No.” She said as she forced herself not to laugh at the absurdity of the situation because what in the fresh hell were the odds? Of all the possible men in the city, her parents had set her up with Simon Caldwell.
“Neither did I.” He said, voice cool and measured.
A strange, heavy silence stretched between them, both parties heavy with unspoken thoughts. Ali could hear her heartbeat in her ears and her palms were starting to become slick with sweat.
She should leave.
She should turn around, call her mother, and demand for an explanation.
Despite these should have’s, she didn’t move and neither did Simon.
He tilted his head silightly, something like amusement flickering in his gaze. “Well, this is unexpected.”
That was one way to put it, Ali thought.
She shifted on her feet and glanced towards the entrance considering her escape route. She didn’t owe him anything. She didn’t need to sit here and endure whatever version of a forced conversation this would be but before she could make her decision Simon spoke up. “You could walked out.”
The way he said it, like a challenge, made her bristle. She narrowed her grey eyes at him. “And let my mother win? Not a chance.”
The corner of his lips twitched, it was the closest thing to a smile that she has ever seen from him. “Then I supposed we’re having dinner then.”
Ali slowly exhaled through her nose and lowered her onto the seat across from Simon. She didn’t what this was, why she was still here, but if there was one thing she hated more than blind dates, it was backing down from a challenge.
Simon studied her for a beat longer before signaling for the waiter. As if the moment has been settled in his mind, as if this wasn’t utterly bizarre.
She folded her hands gracefully on the table, watching him carefully. “So, how exactly did you end up here?”
Simon didn’t hesitate. “My sister.”
She wasn’t expecting that at all. “You sister?”
He nodded, his expression unreadable under the carefully placed stoic mask he had on. “She thinks I work too much. Apparently, that means I need to be forced into social situations like this one.”
Ali let out a quiet scoff of amusement. “That makes the two of us.”
Simon didn’t immediately react, but something in his eyes shifted, like he found that detail somewhat interesting. “Your parents?”
Ali sighed softly. “My mother thinks I’m running out of time.”
For the first time, a faint trace of amusement crossed his face. “I suppose we habe more in common that I thought.”
She blinked at that, surprised by his tone. She had always assume Simon Caldwell was void of anything resembling humor. Yet here he was, making what could almost be considered as a joke.
The waiter finally arrived, asking if they would like to start with drinks. Ali barely registered the exchanged as Simon smoothly ordered a scotch then glanced at her.
“Wine,” she said, her voice steadier than she felt.
The waiter left leaving them alone again, and Simon turned his attention back to her. “Since we’re both stuck here, perhaps we should make the most of it.”
Ali arched an eyebrow. “And how do you propose we do that?”
A beat of silence passed between them. Then, with a calmed that sent a shiver down her spine, Simon leaned back in his chair, regarding her with something unreadable. “We pretend this is real.”
She inhaled sharply. “What?”
His lips curved. Not quite a smirk but it was close enough to be one. “Think about it.” He paused for a moment. “Your mother wants you to meet someone. My sister wants me to spread my social butterfly wings. If we both play along, we both win.”
Ali should have immediately said no. She should have shut the entire idea down before it could even take root.
But instead, she found herself considering it.
The alternative was suffering more setups, more forced conversations, more suffocating pressure; but if she and Simon pretended just for the night, maybe it would buy them both some peace even just for a little while.
She hesitated, watching him. He was still waiting, his expression unreadable, his gaze unwavering. Like he already knew what she was going to say.
Ali exhaled slowly and steadily.
Then, against her better judgment, she nodded.
“Fine.” She grumbled. “Let’s pretend.”