Single Dad Fixed Female CEO’s Computer And Accidentally Saw Her Photo. She Asked Am I Pretty? Part 2

An Unexpected Invitation

James stared at his phone, reading Olivia’s message for the tenth time that morning. “Dinner tonight, my place at 7. I want to thank you properly for saving my files.”

His thumb hovered over the reply button, uncertainty gnawing at him. It had been three days since he’d fixed her computer at Montgomery Enterprises.

It had been three days since that unexpected moment when she’d caught him looking at her photo. She had asked that disarming question, “Am I pretty?”

The memory still made his cheeks burn. He had stammered like a schoolboy, eventually managing to tell her that yes, she was beautiful.

He had added that it was unprofessional of him to say so. To his surprise, she’d smiled.

It was not the polished corporate smile he’d seen in press photos. It was something genuine that transformed her face and stayed with him long after he’d left her office.

James glanced at the framed photo of Emma on his bedside table. His late wife’s smile seemed to encourage him, as it had for the five years since her passing.

“What would you think of this, M?” he whispered. His daughter Lily’s voice interrupted his thoughts, calling from the kitchen.

At twelve years old, she was fiercely independent but still needed him more than she’d admit. She was attempting to make pancakes.

“Dad, the pan is doing that smoking thing again.” With a sigh, James typed a quick reply.

“I’d like that. Can I bring Lily?” He went to rescue breakfast.

He couldn’t leave his daughter alone for the evening. He wasn’t ready to date without considering her feelings first.

If Olivia Montgomery, CEO of one of the city’s largest tech companies, had a problem with that, then dinner wasn’t meant to be. His phone pinged with her reply as he flipped a slightly charred pancake.

“Of course! I’d love to meet her.” Across town, Olivia set her phone down and stared out the floor-to-ceiling windows of her penthouse apartment.

The city sprawled below, a landscape of ambition and achievement that had consumed her life for the past decade. At thirty-eight, she had everything she’d worked for.

She had professional success, financial security, and respect in her industry. She had everything except someone to share it with.

She walked to her closet, suddenly anxious about dinner. It had been years since she’d invited anyone to her home who wasn’t a business associate or old friend.

James was different. There was something refreshingly genuine about the IT consultant who’d been called in when her executive tech team couldn’t recover her corrupted files.

He hadn’t been intimidated by her position or tried to impress her. He’d simply done his job with quiet competence until that moment when she’d caught him looking at her personal photos.

The picture had been taken on a rare vacation two years ago. It showed Olivia on a beach at sunset, hair loose, laughing at something off camera.

It was not the polished executive image she presented to the world. When she’d asked if he thought she was pretty, she’d surprised herself as much as him.

It was impulsive, unprofessional, and completely unlike her. Yet, his flustered, honest response had touched something long dormant inside her.

Now she was cooking dinner for him and his daughter. Olivia checked her refrigerator, realizing with dismay that it contained little more than takeout containers and a bottle of champagne.

She’d need to go shopping, another activity that had fallen by the wayside in her busy life. What did twelve-year-old girls even eat?

The thought made her stomach tighten with anxiety. She hadn’t been around children since she was one herself.

As evening approached, James found himself standing before his closet. Lily perched on his bed, offering unsolicited fashion advice.

“Not the blue shirt, Dad. You wear that to all your client meetings. It’s boring.”

“I am meeting a client,” he protested weakly. Lily rolled her eyes with all the dramatic flare of early adolescence.

“At her house? For dinner? With me as your wingman? This is totally a date.”

“It’s not a date,” James insisted, though he set the blue shirt aside. “Ms. Montgomery is just grateful I recovered her files.”

“And don’t say wingman. Where do you even learn these terms?”

“The internet exists, Dad.” Lily flopped back on the bed.

“And I’m not a baby. Mom’s been gone five years. It’s okay if you like someone.”

James paused, a dark green henley in his hands. Sometimes his daughter’s maturity caught him off guard.

It was a painful reminder of all she’d had to process at such a young age. “Lily, it’s not that simple.”

“It never is in those books you read,” she said. She referred to the mystery novels that filled his nightstand.

“But real life doesn’t have to be so complicated. Just wear the green one. It brings out your eyes.”