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

Invented Crises and a Bold Invitation

Three days later, James was elbow-deep in a server repair at a dental office when his phone rang with an unfamiliar number. “Mitchell IT Services,” he answered, wedging the phone between his ear and shoulder.

“Mr. Mitchell, this is Vivien from Harrington Enterprises”. “Ms. Harrington would like to know if you’re available for another consultation this afternoon”.

James checked his schedule. He had a 4:00 p.m. appointment to set up a new point of sales system at a boutique downtown, but his afternoon was otherwise open.

“I could come by around 2 p.m. What seems to be the problem?”. There was a pause on the other end of the line.

“Ms. Harrington will explain when you arrive”. That was odd, but James didn’t question it.

Business was business, and Harrington Enterprises could afford his rates. When he arrived at the 42nd floor this time, Vivien led him not to Eliza’s office, but to a large conference room.

Several people in business attire were gathered around a table strewn with laptops and tablets. Eliza stood at the head of the table, looking much more like the CEO he’d expected the first time.

Her hair was perfectly styled, and she wore a tailored navy suit that probably cost more than his monthly rent. She looked up when he entered, and for a moment, he thought he saw relief in her eyes.

“Mr. Mitchell, thank you for coming on such short notice,” she said formally. “We’re having some issues with our presentation system, and our IT team is tied up with a server migration”.

James nodded, setting down his bag. “What seems to be the problem?”.

For the next hour, James worked on connecting the conference room’s presentation system to various devices. He fixed compatibility issues and ensured everything ran smoothly for what appeared to be an important client meeting.

The work wasn’t particularly challenging. He couldn’t help wondering why they’d called him specifically when any IT professional could have handled it.

As the meeting participants began to file out, Eliza approached him. “Thank you again. You’ve been a lifesaver twice now”.

“Happy to help,” James handed her the invoice. “Though I have to say, this seemed like something your in-house team could have handled”.

Eliza took the invoice, a slight smile playing at her lips. “Perhaps, but I trust your work”.

Before James could respond, a tall man in an expensive suit approached them. “Eliza, we need to discuss the Westridge proposal before tomorrow”.

“Of course, Richard”. She turned back to James. “Thank you for your time, Mr. Mitchell”.

Just like that, he was dismissed. As Vivien escorted him back to the elevator, James couldn’t shake the feeling that there had been more to this service call than a simple technical issue.

His suspicions were confirmed a week later when he received another call from Harrington Enterprises. This time, it was about a critical issue with Eliza’s home office setup.

Then it happened again the following week when he was asked to troubleshoot her company laptop, which was running unusually slow.

By the fourth call in as many weeks, James was certain Eliza Harrington was inventing reasons to see him. She was the CEO of a tech company with its own IT department.

The realization both flattered and terrified him. Women like Eliza didn’t date men like him: single fathers with struggling businesses and apartments in unfashionable neighborhoods.

Whatever game she was playing, he couldn’t afford to be a part of it. So when Vivien called to schedule yet another consultation, James made a decision.

“I’m sorry, but I’m booked solid for the next few weeks,” he lied. “I can recommend another consultant who might be able to help”.

There was a pause on the other end of the line. “One moment, please”.

A moment later, Eliza’s voice came through the phone. “Mr. Mitchell, is there a problem with our account?”.

James closed his eyes, gathering his courage. “No, Ms. Harrington. I just don’t think I’m the right fit for your ongoing IT needs”.

“Your company would be better served by someone with a larger operation”. “I see”.

Her voice was cool and professional. “May I ask why you’ve come to this conclusion?”.

“Because,” James said, taking a deep breath, “I think we both know these service calls aren’t really about IT issues”.

The silence that followed was so long that James wondered if she’d hung up. “You’re right,” she finally said, her voice softer now. “They’re not”.

James hadn’t expected her to admit it so readily. “Ms. Harrington—”. “Eliza,” she corrected.

“Eliza,” he conceded. “I’m flattered, but—”.

“Have dinner with me,” she interrupted. “Just once, and if you still want to refer me to another IT consultant afterward, I’ll respect that”.

James thought about all the reasons he should say no. He thought of the class difference, the professional boundaries, and the fact that his life was complicated enough.

But then he thought about her question that first night, “Am I pretty?”. The vulnerability behind it had stayed with him.