After confirming dinner with Jack, your nerves skyrocketed. You and Y/F/N stood off to the side of Grand Central Market, still trying to process what had just happened.
“You’re actually going on a date with Jack Flaherty,” Y/F/N said again, her voice barely containing her excitement. “Do you realize how insane this is?”
“I’m realizing it,” you said, holding up the baseball with his signature and phone number like it was a golden ticket. “What do I even wear? What do I say? This doesn’t feel real.”
“Relax,” Y/F/N said, grabbing your shoulders and shaking you lightly. “You’ve got this. You just need to stay cool and be yourself. He already likes you enough to give you his number. The hard part’s done.”
You gave her a look. “You call this the hard part? What about actually going to dinner with him?”
She laughed. “Okay, fair. But seriously, you’ll be fine. Now, let’s get you ready.”
A couple of days later, the hours passed in a blur of preparation. Y/F/N insisted on helping you pick an outfit, do your hair and makeup and calm your nerves. By the time evening rolled around, you were a mix of excitement and anxiety. You checked your phone one last time to confirm the address Jack had sent for the restaurant—a cozy, upscale spot not far from the market.
When you arrived, Jack was already waiting outside. He was dressed casually in a button-up shirt and jeans, looking effortlessly cool. When he saw you, he smiled, and for a moment, your nerves melted away.
“Hey, Y/N,” he said, stepping forward. “You look amazing.”
“Thanks,” you said, feeling your cheeks heat up. “You too.”
He held the door open for you, and the two of you stepped inside. The restaurant was intimate, with warm lighting and the faint hum of conversation. Jack had reserved a quiet table in the corner, away from prying eyes.
“So,” he said once you were seated, “I have to admit, I’ve never done this before.”
“Done what?” you asked, your curiosity piqued.
“Given my number to someone at a signing,” he said, a sheepish smile spreading across his face. “But there was something about you. I couldn’t let you just walk away.”
Your heart skipped a beat at his words. “Well, I’m glad you didn’t.”
The conversation flowed easily from there. Jack was charming and down-to-earth, and you found yourself forgetting he was a famous athlete. He asked about your interests, your favorite baseball moments, and what you liked to do for fun. In turn, he shared stories from his career—funny moments with teammates, the pressure of playing in big games, and his love for tacos, which explained why he’d chosen Villa’s Tacos for the event.
By the time dessert arrived, you were laughing like old friends. Jack leaned back in his chair, his eyes warm as he looked at you. “This has been… really nice,” he said. “I’m glad you came.”
“Me too,” you said, feeling a flutter in your chest.
When the check came, Jack waved it away, insisting on paying. “I said dinner was on me, remember?”
Outside, the night air was cool, and the streets were quieter than before. Jack walked you to your car, his hands tucked in his pockets. He seemed nervous, which made you smile—seeing this side of him felt even more special.
“Can I ask you something?” he said, stopping a few steps from your car.
“Of course,” you said.
“When can I see you again?” His voice was soft, almost uncertain. “I know my schedule’s crazy, but I’d really like to spend more time with you.”
Your heart swelled at his words. “ Anytime I’d like that too.”
Jack smiled, and for a moment, you thought he might kiss you. But instead, he reached out and took your hand, his thumb brushing over your knuckles. “Good,” he said. “I’ll text you.”
As you drove home, the signed baseball sat in the passenger seat, a reminder of the surreal day you’d just had. Y/F/N was waiting for you when you walked in, practically bursting with anticipation.
“Tell me everything!” she demanded.
You grinned, feeling a warmth you couldn’t quite describe. “It was perfect.”
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