The Cold CEO Fires His Blind Dates Like Secretaries

Damon Cross didn’t believe in dating.

He believed in deals. Partnerships. Strategic mergers. Marriage, to him, was a contract—not a love story. So when his grandfather forced him into blind dates through a matchmaking agency, he treated them like failed business meetings from the start.

Three dates. One day. All disasters.

⸻

Date One: The Late Offender

The woman arrived exactly two minutes late.

Damon didn’t even wait for her to sit before glancing at his Rolex and scoffing.

“You’re two minutes late,” he said flatly.

She smiled politely. “Oh, I’m so sorry. Parking—”

“That’s one minute and forty-eight seconds of my life I will never get back,” he cut in, dead serious. “Do you know what I could’ve done with those minutes?”

The woman blinked. “Um…”

“I could’ve closed two international deals, fired someone mediocre, and still had time to admire my reflection in the elevator mirror.”

Her face fell.

Damon simply waved the waiter over. “Cancel the wine. We won’t need it.”

Ten minutes later, she stormed out, muttering something about needing therapy.

⸻

Date Two: The Coffee Stirrer

The second woman was cheerful and sweet. A little too sweet. She wore a pastel blue dress and had her hair curled like she’d stepped out of a 1950s diner.

She ordered a cappuccino. Stirred it gently. Clockwise.

Damon watched, horrified.

“You stirred your coffee… clockwise,” he said slowly, as if she had just committed a crime.

She looked confused. “Uh… yeah?”

“That tells me everything I need to know.”

“What?”

“You follow the crowd,” he explained coldly. “No originality. A woman of value would stir counter-clockwise. Assert dominance over her beverage. I can’t be with a follower.”

She blinked. “Are you serious?”

“As a hostile takeover,” he replied, lifting his espresso and sipping it like he was judging the beans personally.

She stood up and poured the rest of her cappuccino into his empty water glass before walking away.

⸻

Date Three: The Squeaky Heels

He didn’t even sit for the third one.

She walked in—tall, stylish, beautiful. But the moment her heels hit the marble floor—

Squeak. Squeak. Squeak.

Damon’s face twisted in pain.

She smiled and greeted him. “Hi, I’m—”

“No.”

“Excuse me?”

“Your heels are squeaky,” he said, already pulling his wallet out. “That sound is assaulting my eardrums. If I wanted to be reminded of a cartoon duck walking across a marble floor, I’d have stayed home and tortured myself.”

She gasped.

He handed her a hundred-dollar bill. “Buy shoes that respect acoustics.”

She slapped the money back on the table and walked out with her squeaky dignity intact.

⸻

By evening, the matchmaking agency had had enough.

They called Damon’s grandfather, Mr. Cross Sr., directly.

“We’re sorry, sir,” the agent said, barely hiding her exhaustion. “Mr. Damon Cross is… unmatchable. We will not be arranging any more dates for him.”

“What happened?” the old man asked from the other end.

“I think young Mr. Cross is too good to even be matched with anyone,” the woman from the matchmaking agency said as she explained everything in detail to Mr. Cross.

⸻

Later That Night – Hospital Room

Damon showed up at the hospital with his usual annoyed look, dressed in a crisp black suit as if coming to negotiate his grandfather’s life, not check on it.

His grandfather, white-haired and pale but still sharp, stared at him from the bed with a smirk.

“So,” the old man said. “Here he comes to finally visit the dying man.”

“You’re not dying, Grandpa. You’re being dramatic. All you need is just the surgery. And I’m really working toward the condition you gave.”

“Oh, what a good grandson. Working toward getting married and dismissing blind dates. One stirred cappuccino clockwise, one was two minutes late, and the third wore noisy heels. You’re really working hard toward marriage—just as I asked.”

“Grandpa, you needed to be there today and see what those ladies were doing. If they were my workers, it wouldn’t take me a minute to sack them all.”

“Very good of my grandson—treating marriage like a business. Dismissing blind dates like he’s firing staff. By the look of things, I think I need to start preparing my funeral myself. Because you’re clearly not getting married anytime soon. And I still stand by what I said—if you don’t get married, I won’t lie down on that surgery table.”

Damon walked over and held his grandfather’s hand.

“Grandpa, you need to understand. Those women today were not… qualified.”

“Qualified? You’re not hiring a CFO. You’re finding a wife, you idiot.”

“Same thing,” Damon snapped. “Marriage is business. Mergers. Responsibilities. There should be interviews, contracts, terms.”

“And what exactly disqualified the last three?”

“The first was late. The second stirred coffee like a peasant. The third squeaked.”

The old man blinked. “You’re… not well. I think you should be the one on this bed instead of me. Or better still, we can ask the doctor to find you a bed beside mine. Because you need one.”

“Grandpa, are you saying I’m being too selective?”

“Noooo. You’re not selective. You’re psychotic.”

Damon turned, frustrated. “That’s why I think—from my ‘psychotic’ point of view—marriage isn’t necessary. No need to get married. And if by chance I do need to get married for your sake—because I need you and don’t want anything to happen to you—the person should at least meet my standard. I’m handsome. I’m rich. I’m well-educated. I’m smart. In fact, I’m perfect. I don’t think any woman is worthy of me. And if by chance you think I need one, she better be my exact image to even come close.”

There was a pause.

His grandfather sighed, shook his head, and reached for the drawer beside his bed.

“It’s not your fault—it’s mine. For raising you only to think in terms of business. Fine. If you want to be that cold-hearted, I’ll give you someone who matches your temperature.”

He pulled out a card and handed it to Damon.

“Her name is Lydia Williams. Daughter of an old business associate. Smart. Sharp. Her father owns one of the biggest conglomerates on the West Coast. She’s been trained for deals like this.”

Damon studied the card.

“Give her a chance,” his grandfather said. “Or start planning my funeral.”

Damon tucked the card into his breast pocket and muttered, “Fine. Anything for you, old man.”

As he walked out of the hospital room, the old man called after him, “Oh, and Damon?”

“What?”

“If this one dumps you too, I’m donating my brain to science before the tumor eats it.”