Page 27 of Most Eligible Boss

“You know, I hadn’t even thought about it,” she said. “Yesterday, we were talking about relationships, and I was pushing you to try to meet someone new, but I never asked if maybe you already have been dating. Anyone new in your life?”

I chuckled softly. "Well, there was someone I connected to, but it wasn’t workable."

Stefanie arched an eyebrow and leaned forward, curiosity piqued. "Oh? How come?"

Sighing inwardly, I realized I had opened the door for this conversation, and there was no way to back out of it now.

"It's complicated, Stef. She's a colleague, and our professional dynamic made things... challenging."

Stefanie couldn't hold back her laughter at my vague reply.

"Jeremy, you always manage to complicate matters unnecessarily. You’re like a robot on autopilot, going through life's motions but forgetting to experience it. Life is too fleeting to get so caught up in mundane crap. So what if you work together? You’re mature enough to leave home life at home. Make it work!"

"I know, I know," I admitted with an affectionate grin. "I suppose I have the tendency to overanalyze. I never look at what’s good about something. I think about the hundred and ten ways it can go wrong."

Relaxing back into her chair, Stefanie looked thoughtful.

"Jeremy, sometimes you just have to take a leap of faith. You never know what might happen until you try."

"I suppose you're right," I conceded. "I just need to work at having balance in my life."

"Exactly,” she said. “Life is a balancing act that, in the end, is just all about taking risks. I know you can do it. I’ve seen you in action. You’ve taken huge risks in your life, so risk your heart. It will pay off eventually. I promise."

From there, we let the conversation shift to other topics. Then, as the evening gradually drew to a close, Stefanie and I said our last goodbyes for a while. As always, I was thankful for her visit.

Her words reignited a sense of purpose, reminding me that life demanded living, even if it also demanded embracing the unknown.

Feeling determined, I decided to reach out to Jill. It was a simple gesture needed to initiate a long-overdue conversation.

The idea of digging into our mutual feelings, fears, and hopes for the future thrilled and unnerved me. I also wanted to know if this was a conversation that Jill would be willing to have.

With all that in mind, I reached for my phone and wrote a text, each keystroke feeling like a stride in the right direction.

“I miss you.”

I tapped send and waited, seconds stretching into an eternity as I ached for a response.

However, minutes elapsed into hours without any sign of acknowledgment from Jill. Doubt crept in, leaving me feeling foolish for reaching out at all.

As I stared at my silent phone, disheartened by the absence of a reply, I realized that perhaps I had completely misconstrued the situation.

Maybe she needed to be prepared to hear from me again. Perhaps I was too impulsive. Maybe I was the only one whose feelings felt wrapped up in the possibility of Jill and me having a future together, and perhaps she had already moved on.

Maybe Boston hadn’t meant anything at all.

With a sigh of resignation, I set my phone down, giving in to my disappointment. Despite my best intentions, this was now beyond my control.

If Jill harbored her apprehensions and reservations, that was simply a reality I would have to respect.

Lying in bed, questions swirled around my mind about Jill’s true feelings and what the morning back at the office might have in store for both of us. Our time together had been wonderful- but maybe it would only ever be just the one weekend in Boston. Perhaps it wasn’t meant to go any further than that.

I grabbed my phone off the nightstand and gave it one final glance before I laid it back down again. I was still waiting for a message back.

With a sigh, I rolled over and soon fell asleep.

As the sun peeked through the curtains the following day, I realized I had sent the text from my personal cell number that she wouldn’t have recognized. I panicked and thought about how to remedy the situation. I decided to text her again from my work cell phone that she had. After thinking about it all night, I realized that her not responding to my previous text was a blessing in disguise, as maybe she had already moved on.

"Hey, Jill. Would you like to grab lunch tomorrow? There's something important I'd like to discuss with you."

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