I Asked My Boss To Pretend To Be My Girlfriend When I Met My Ex.She Said: “So What Do I Get?A Kiss
The first time I saw my ex again was the moment I realized how unfinished some wounds can feel even years later. I stood in the parking lot of a quiet countryside cafe in upstate New York. My chest tight, my hands cold despite the summer air, knowing she would walk through that door any second. I had told myself I was over it, that time had done its work.
But fear has a way of exposing lies we tell ourselves. I was there for a casual reunion with old friends, but I knew she would be there, too. And the thought of facing her alone made my confidence crumble. That was when desperation pushed me into making the boldest request of my life, asking my boss to pretend to be my girlfriend for one afternoon.
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My name is Matthew Collins, and at the time, my life looked stable from the outside. I worked as a project coordinator for a midsized construction firm based in Pennsylvania, a respectable job with steady hours and decent pay. My boss, Rebecca Turner, was everything I wasn’t. Confident, composed, and effortlessly respected. She had built her career brick by brick, earning authority not through intimidation, but through consistency and integrity.
Everyone admired her, including me, though I kept that admiration safely tucked behind professional boundaries. She was the last person I expected to turn to when my past threatened to undo me. My ex, Hannah Brooks, and I had ended things 2 years earlier after a long, emotionally exhausting relationship. We had loved each other deeply, but love alone hadn’t been enough to fix the cracks caused by miscommunication, timing, and unresolved pain.
When she left, it felt like a quiet earthquake. Nothing dramatic on the surface, but inside, everything shifted. I spent months rebuilding myself, learning to stand alone again. I thought I had healed until an invitation arrived, announcing a small reunion at a countryside cafe we used to visit together. The idea of running into Hannah, possibly seeing her happier, stronger, maybe even in love again, stirred an old ache I wasn’t prepared to face alone.
The idea came to me suddenly, half-formed and ridiculous. I needed a buffer, someone who made it clear I had moved on, too. The problem was, I had no one to ask. Most of my friends were busy or lived out of state. Then there was Rebecca. She was attending the same gathering because her sister-in-law owned the cafe. I remembered her mentioning it casually in a meeting, and the thought stuck.
The more I considered it, the more impossible it seemed. Yet, the desperation outweighed the fear of embarrassment. When I finally asked her, my voice shook with humility and honesty. I explained my situation, my anxiety, and my ridiculous plan. I didn’t expect her to say yes. I expected polite refusal, maybe a gentle reminder about professionalism.
[clears throat] Instead, she surprised me by listening quietly, her expression thoughtful rather than judgmental. She didn’t laugh or dismiss me. She simply considered it, weighing something deeper than the request itself. She agreed, but not without conditions. She made it clear this wasn’t about pretending to be something we weren’t, but about standing beside someone who needed support.
She teased lightly, asking what she would get out of it and joked about a kiss being her reward. It was said playfully, but my heart reacted in ways I didn’t expect. Beneath the humor, there was warmth, and beneath the warmth, something that felt like trust. The day of the reunion arrived, wrapped in sunlight and nerves.
The cafe sat near a field of wild flowers, wooden picnic tables scattered across the grass, laughter drifting through the air. When Rebecca arrived, dressed casually but elegantly, something shifted inside me. She didn’t look like my boss that day. She looked like someone who chose to be there for me.
As we walked together toward the tables, her presence steadied me. She didn’t overplay the role or act unnatural. She simply stood close, her energy calm and reassuring. Seeing Hannah again was harder than I imagined. She looked different, lighter somehow, as if life had been kinder to her since we parted.
For a moment, old insecurities clawed their way back. But Rebecca didn’t flinch. She greeted everyone with warmth, introducing herself as someone important in my life without exaggeration or awkwardness. Her confidence filled the space between us, and slowly, my tension eased. Throughout the afternoon, I noticed things I’d never seen before.
Rebecca’s laugh wasn’t just polite. It was genuine and full. She listened deeply when others spoke, making them feel heard. She touched my arm occasionally, not to perform affection, but to remind me Iwasn’t alone. Each small gesture felt intentional, grounding me in the present instead of the past.
As hours passed, something unexpected happened. The act stopped feeling like an act. I wasn’t thinking about Hannah anymore or how I appeared. I was thinking about how natural it felt to be beside Rebecca, how safe I felt in her presence. It scared me because it made me realize how long I’d been settling for emotional distance in my life.
When Hannah eventually approached us, the moment I had feared most arrived quietly. There was no confrontation, no jealousy, just a calm exchange of pleasantries. I realized then that the power she once held over my emotions was gone. I didn’t need validation or comparison anymore. I was standing in a different chapter of my life, one I hadn’t known I was ready to begin.
As the gathering began to wind down, Rebecca and I sat at one of the picnic tables, the sun dipping low and casting long shadows across the grass. There was a comfortable silence between us, the kind that doesn’t demand words. I felt gratitude swelling in my chest mixed with something more fragile and hopeful. I thanked her not just for pretending, but for showing up when I needed someone the most.
That was when she leaned in and gave me the kiss she had jokingly mentioned before. It was brief, gentle, and full of meaning that went beyond performance. It wasn’t about proving anything to anyone else. It was about acknowledging something real that had quietly grown between us. In that moment, I felt a sense of clarity I hadn’t experienced in years.
Life didn’t change overnight after that day. But something fundamental shifted. At work, we maintained our professionalism, but there was an unspoken understanding between us. We took things slowly, respecting boundaries and letting trust guide us rather than impulse. Over time, what began as a favor rooted in kindness evolved into a partnership built on mutual respect, faith, and shared values.
Looking back, I realized the story isn’t about pretending or impressing an ex. It’s about the courage to ask for help and the humility to accept it. It’s about how God sometimes places the right people in our lives at the exact moment we need them, even when we least expect it. Rebecca wasn’t just my boss or a temporary shield against old pain.
She became a reminder that love can arrive quietly through acts of compassion and understanding. If this story touched your heart, if it reminded you that healing is possible and that new beginnings often start in unexpected ways, please take a moment to like, comment, and share this video. Your engagement helps keep these stories alive and reaching those who need them.
And before this story ends, I want to ask you one more thing. Leave a comment telling us about a moment when someone showed up for you when you didn’t expect it. Sometimes sharing our stories is the first step toward healing. I walked into that cafe afraid of my past, but I walked out carrying hope for the future.
And that more than anything is how I knew my life was finally moving forward.
