Blind Date

Ali tugged at the hem of her dress for what had to be the hundredth time in the past five minutes. The smooth silk felt foreign against her fingertips, unfamiliar in the same way this entire situation did. She hated blind dates. She hated the forced pleasantries, the expectations, the awkwardness. But most of all, she hated that her parents had set this one up. “You’re twenty-nine, Ali,” her mother had said, her tone laden with disappointment and urgency all at once. “You’re not getting any younger.” As if she needed the reminder. Ali exhaled slowly, glancing around the dimly lit restaurant, a place clearly designed to scream sophistication. The quiet hum of conversation, the occasional clink of wine glasses, the soft flicker of candlelight—all of it felt suffocatingly intimate for a date she already knew was doomed. She didn’t even know the man’s name. Her mother had only gushed about his career—something finance-adjacent, Ali had stopped listening halfway through—and how ‘perfect’ he was. Because ‘perfect’ to her mother simply meant successful. She would’ve protested more, but she was exhausted. If one dinner got her out of another month of passive-aggressive comments, she’d endure it. But then she saw him. Or rather, recognized him. Ali stopped mid-step, her stomach twisting into a painful knot. Sitting at the table—her table—was Simon Caldwell. Her ex’s boss. Her pulse stuttered, then surged forward with a vengeance. This couldn’t be happening. Simon Caldwell was the last person she wanted to see, let alone sit across from for an entire meal. He was ruthless, intimidating, the kind of man who never wasted words and expected perfection. She had only met him a handful of times when she was still with Daniel, but each encounter had left a lasting impression. Simon was the reason Daniel had spent countless late nights at the firm. The reason Daniel had complained about the relentless pressure to be better, to work harder. Simon was the one Daniel had resented most—until he had turned that resentment on her instead. And now, he was here. He looked just as imposing as she remembered, dressed in a sharp black suit, his dark hair neatly styled, his expression unreadable as he scrolled through his phone. Even seated, he exuded power, control, a presence that commanded attention. Ali barely managed to move forward, her limbs stiff as she approached. 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—surprise, maybe, or mild recognition—but it disappeared just as quickly as it had come. He arched a brow, setting his phone aside. “Ali.” Her stomach clenched. He remembered her. She forced a breath. “You’re my blind date?” Simon didn’t answer right away, his gaze steady as he studied her. Then, as if coming to some conclusion, he let out a quiet sigh, barely perceptible. “I take it you didn’t know.” “No.” She fought the urge to laugh, because what were the odds? Of all the men in the city, her parents had unwittingly set her up with Simon Caldwell? “Neither did I,” he said, voice cool, measured. A strange silence stretched between them, heavy with unspoken thoughts. Ali could hear her heartbeat drumming in her ears, could feel the way her palms had begun to sweat. She should leave. She should turn around, call her mother, and demand an explanation. But she didn’t move. And neither did Simon. He tilted his head slightly, something almost amused flickering in his gaze. “Well. This is unexpected.” That was one way to put it. She shifted, glancing toward the entrance, considering her escape route. She didn’t owe him anything, 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 again. “You could walk out.” The way he said it—like a challenge—made her bristle. She narrowed her eyes. “And let my mother win? Not a chance.” Something in the corner of his mouth twitched, the closest thing to a smile she’d ever seen from him. “Then I suppose we’re having dinner.” Ali exhaled sharply and lowered herself into the seat across from him, her body still coiled with tension. She didn’t know what this was, didn’t know 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 had been settled in his mind. As if this wasn’t utterly bizarre. She folded her hands on the table, watching him. “So, how exactly did you end up here?” Simon didn’t hesitate. “My sister.” That caught her off guard. “Your sister?” He nodded, his expression unreadable. “She thinks I work too much. Apparently, that means I need to be ‘forced into social situations.’” Ali let out a quiet scoff. “That makes two of us.” Simon didn’t react immediately, but something in his eyes shifted, like he found that detail somewhat interesting. “Your parents?” Ali sighed. “My mother thinks I’m ‘running out of time.’” For the first time, a faint trace of amusement crossed his face. “I suppose we have more in common than I thought.” She blinked at that, surprised by his tone. She had always assumed Simon Caldwell was void of anything resembling humor. Yet here he was, making what could almost be considered a joke. The waiter arrived, asking if they’d like to start with drinks. Ali barely registered the exchange as Simon smoothly ordered a scotch, then glanced at her. “Wine,” she said, her voice steadier than she felt. The waiter left, and Simon turned his attention back to her. “Since we’re both stuck here, perhaps we should make the most of it.” Ali arched a brow. “And how do you propose we do that?” A beat of silence. Then, with a calmness 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 close. “Think about it. Your mother wants you to meet someone. My sister wants me to ‘open up.’ If we play along, we both win.” Ali should’ve immediately said no. Should’ve shut the entire idea down before it could take root. But instead, she found herself considering it. The alternative was suffering through more setups, more forced conversations, more suffocating pressure. But if she and Simon pretended—just for tonight—maybe it would buy them both some peace. 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, steadily. Then, against her better judgment, she nodded. “Fine,” she murmured. “Let’s pretend.”