Page 26 of Most Eligible Boss

“He’s clever enough to have stuck with me all these years,” she said with a smirk, pulling her warm coffee mug to her lips as her eyes scanned the lunch menu. “I think I might try the spinach rolls. Have you had them? Any good?”

I nodded. “They’re one of my favorite things here, but today, I’m going for a chicken and kale salad.”

We placed our order on the tablet at our table, then leaned back to chat more as we waited.

“How long have you and Brian been together?” I finally asked. “Twelve? Thirteen years?”

She nodded. “It will be twelve in November.”

“Is his mom still nagging you to get married?” I smirked.

She giggled and shook her head. “She finally gave up.”

We both laughed. Then, she looked at me mischievously.

"Speaking of relationships," she casually mentioned, "Did you hear about Sarah's engagement?"

I mustered a strained smile, although an internal storm of emotions churned within me. Sarah was my ex, who had left me for another man she was now set to marry.

"Yes, I did," I responded with an unmistakable lack of enthusiasm. "It's truly wonderful for her."

“Well, I stand by what I have always said; she made a stupid mistake letting you go,” she said, sensing the tension in my reply. She then swiftly diverted the conversation.

As we continued our meal, our discussion meandered towards lighter topics, and I found myself surrendering to a sense of rare relaxation in my sister's presence. She had an innate ability to ground me—to remind me that life extended beyond the realm of work and the burdensome weight of my past.

Yet beneath this serenity lurked the lingering sting caused by the mention of Sarah's engagement—an unwelcome reminder of my reluctance to embrace love and commitment. I had constructed impenetrable walls around my heart—barriers that seemed impossible to dismantle.

Stefanie tenderly squeezed my hand as our lunch drew close, her eyes brimming with empathy and support. "Remember, Jeremy, you deserve happiness too," she whispered.

I nodded, thankful for her words, as I watched her get up and put her jacket back on before giving me one last hug, then exiting the café to hail a cab back to her hotel.

Returning to the confines of the office, I found myself profoundly contemplating our conversation. The wounds inflicted by my past still festered. Nevertheless, with time and the right kind of support, I could summon the courage to dismantle those walls and embrace the possibility of a brighter future.

Stefanie's words echoed in my head as I settled into my chair, idly sipping on the now lukewarm cup of coffee.

She had mentioned Sarah's engagement—which still provoked anguish—yet she had also imparted wisdom that proved difficult to ignore.

"You deserve happiness too," she had assured.

I knew deep down she spoke the truth; however, exorcising the heartache of the past was far easier said than done. The scars ran deep, and the notion of opening myself up to someone new had proven daunting with Jill.

I sent Stefanie a text expressing my gratitude for her unwavering support.

“Thanks for lunch today,” I typed. “Just wanted to say thanks for your kindness and always being someone I can lean on. Things have been hard. A friendly face helps.”

She responded right away. "You're welcome, Jeremy. Remember, life is too short to dwell on the past. Keep an open heart."

Her words were a gentle prod—a reminder that I needed to venture beyond my comfort zone.

As the day drew to a close, I knew Stefanie's advice held weight. Perhaps it was time to tiptoe into the unknown waters of romance—to relinquish the pain of the past and embrace the untapped potential for a brighter future.

And maybe I’d been wrong to dismiss my feelings for Jill so quickly.

The following evening, after another hard day at work, I sat across from Stefanie in a charming little eatery that she’d selected for our second meal together on her trip to New York. It would be the last for a while. She’d be flying home in the morning.

As we sipped our wine and read through the menu, memories of our previous conversation came to my mind. Stefanie's words struck a chord, and I’d spent most of the day profoundly reflecting.

She seemed to notice I was lost in thought.

---