Blind Date

We Keep Pretending

Ali’s fingers twitched around the stem of her wine glass, the cool surface slick against her palm. Across from her, Simon leaned back in his chair, arms crossed in a way that screamed reluctance. He was every bit as stiff as she remembered—perfectly pressed suit, a jaw that looked like it could cut glass, and eyes that assessed everything with clinical detachment. If she closed her eyes, she could still hear his voice from the handful of times she’d been forced to endure his presence back when she’d been dating Daniel.

But now, she wasn’t just tolerating his presence—she was stuck with him.

He exhaled sharply, shifting in his seat. “So, Ali,” he started, voice smooth but edged with disinterest, “what exactly do you do?”

She arched a brow, letting herself sink back against the cushioned booth. “Wow. Starting with the heavy questions.”

His lips twitched, almost amused, but it disappeared as quickly as it came.

“You already know what I do,” she pointed out.

“I knew what you did two years ago.” He glanced at her over the rim of his glass before taking a slow sip. “People change.”

Her fingers tapped lightly against the table. He wasn’t wrong. Two years ago, she had been fresh out of grad school, eager to start her career in marketing. She had spent months juggling the stress of her new job and her ill-fated relationship with Eric. Two years later, she had walked away from both.

“I’m freelancing now,” she admitted, swirling her wine. “Marketing consulting, mainly for startups.”

His brows lifted slightly, as if impressed despite himself. “No more corporate ladder climbing?”

She let out a small laugh. “Turns out, the corporate world wasn’t for me. I got tired of making rich people richer while pulling sixteen-hour days.”

He tilted his head slightly, his gaze sharpening. “So, you chose instability instead?”

Ali stiffened. “Excuse me?”

Simon didn’t flinch at her tone. “It’s a risky move. Most people wouldn’t choose to gamble their income.”

“Most people,” she echoed. “Are you one of those people?”

A corner of his mouth lifted, but it wasn’t quite a smile. “I prefer certainty.”

Of course, he did. She remembered the stories Eric used to tell about his boss. Simon was known for being calculating, ruthless in negotiations, and utterly predictable in his precision. The type of man who made decisions with logic alone, unmoved by sentimentality.

“Good for you,” she muttered.

For a moment, silence stretched between them, filled only with the murmurs of other diners and the soft clinking of silverware. Ali resisted the urge to pull out her phone and text her parents a long, dramatic paragraph about how this setup was a disaster.

She should have seen it coming.

Her mother had spent the last year subtly—and sometimes not so subtly—pushing her toward marriage, convinced that Ali was running out of time. As if being twenty-nine and single was some kind of personal failing. She had gone along with the setup just to get her parents off her back, expecting an awkward but ultimately harmless dinner with some well-meaning doctor or accountant.

Instead, she got Simon.

“Are you always this fun on dates?” she asked, arching a brow.

His lips twitched again. “Are you always this confrontational?”

“Only when I’m forced to be here against my will.”

His gaze flickered with amusement. “Something we have in common, then.”

Ali sighed, pushing her plate aside. “Alright, let’s just get this over with. Let’s agree that we met, we talked, and it didn’t work out. Then we can tell our parents we tried, and they can stop meddling.”

Simon studied her, expression unreadable. Then, to her surprise, he shook his head.

“That won’t work.”

Her brows pulled together. “Why not?”

“Because if we tell them it didn’t work, they’ll just set us up with someone else.” He leaned forward slightly, voice lowering. “And I don’t know about you, but I’d rather not go through this again.”

She hated that he made a good point.

Ali exhaled, slumping back against the booth. “So, what? We just keep pretending we’re seeing each other?”

He took another sip of wine before setting his glass down. “Something like that.”

She studied him carefully, trying to figure out his angle. “What do you get out of this?”

“A reprieve from my mother’s matchmaking attempts,” he answered smoothly.

Ali narrowed her eyes. “And what happens when they start expecting more? What if your mom wants to meet me? What if my parents start hinting at an engagement?”

He didn’t flinch, didn’t even look surprised. It was like he had already thought it through. “We’ll end it before it gets that far.”

Ali hesitated, tapping her nails against her glass. It was risky, sure, but the alternative was going on even more blind dates.

“Fine,” she muttered. “But this stays simple.”

Simon’s lips curved in something that almost resembled a smile. “Simple,” he echoed.

For some reason, Ali wasn’t convinced.

Two weeks later, Ali found herself questioning every life choice that had led to this moment.

“Relax,” Simon murmured beside her, voice low enough that only she could hear.

Ali shot him a glare, but it lacked real heat. “Easy for you to say. You don’t have my mother watching your every move.”

Simon’s hand was warm against the small of her back, a casual touch that probably looked natural to anyone watching. It was the kind of thing a real boyfriend would do—an unconscious display of familiarity. It made her pulse jump, and she hated that.

She took a slow breath, forcing herself to focus on her surroundings. The restaurant her parents had chosen for this “family dinner” was just pretentious enough to impress her mother, but not so upscale that it screamed special occasion. The kind of place that was perfect for an informal get-to-know-you dinner.

Her mother beamed across the table, eyes practically sparkling. “It’s so wonderful to finally see you two together,” she gushed.

Ali forced a smile, praying it didn’t look too strained. “Yeah. It’s been—” She hesitated. What was the right word here? Fun? Exciting? Bearable? “Nice.”

Beside her, Simon nodded, perfectly at ease. “Ali’s been keeping me on my toes,” he added smoothly.

Her father chuckled, taking a sip of his wine. “That sounds about right. She’s always had a strong personality.”

Ali turned her head just slightly, enough to shoot Simon a look that promised revenge. He only smirked in response, looking thoroughly unbothered.

“So, Simon,” her mother continued, resting her chin on her hands, “tell me—what made you interested in my daughter?”

Ali nearly choked on her water. Simon, for his part, remained composed.

“Well,” he said, pausing just long enough to make it sound convincing, “she’s brilliant, for one.”

Ali blinked.

“She’s sharp, funny, and knows exactly what she wants,” he continued, as if this was something he’d thought about before. “And she doesn’t let anyone push her around.”

Her mother practically swooned.

Ali, on the other hand, had to remind herself how to breathe.

Simon’s words shouldn’t have affected her. This was an act, nothing more. But the way he said it—like he actually meant it—sent a flicker of warmth through her chest.

It was dangerous.

Because this wasn’t real.

At least, it wasn’t supposed to be.

And yet, as Simon reached for his glass, his fingers just barely brushing against hers, Ali found herself wondering:

Had they already crossed the line without realizing it?