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My First [Mid-Life] Heartbreak: A Surgery and Recovery Part 1

  As May unfolded, we fit in as many dates as possible before her upcoming cosmetic surgery—Candlelight Coldplay Orchestra, Train, Open Mic Duo, and karaoke nights. Despite the major conflict of May 15th, we managed to work through the insecurities and frustrations, coming out stronger on the other side. When the big day arrived, her surgery went smoothly. The medical staff assured her she’d be thrilled with the results—and they weren’t wrong. 🫠 After a few weeks of recovery, she would be ready to resume dating, but even without physically seeing each other, our connection never faltered. Conversations flowed effortlessly, and my favorite moments were when we shared music together. Each day, as responsibilities faded into the evening, she was the first person I wanted to talk to. Often, I felt moved by our bond, and I poured those feelings into poetry and songwriting. One evening while she rested in bed, a melody drifted into my mind. I picked up my guitar, laid down a progr...

My First [Mid-Life] Heartbreak: A Jealous, Indignant Rage

  If you’ve followed the first six chapters of the Song Bird saga, you know the story has mostly been filled with fun, excitement, and discovery. But in May of 2025, things took a turn—and for the first time, I felt the sharp edge of heartbreak. It was a Wednesday afternoon. I had just finished a string of long, grueling meetings and called her on my drive back to the office. Over the weekend, she had admitted that our connection was starting to feel more like boyfriend and girlfriend than casual lovers. She carried guilt about that, but I reassured her I wasn’t trying to cause issues for her family. I suggested we could balance affection and romance without letting things get out of hand—and even encouraged her to spend more time enjoying others for a while. She agreed. Our conversation then shifted to the reasons behind certain boundaries. That’s when she used an analogy that hit me like a punch to the gut. She said something along the lines of: “If a child had its favorite...

My First [Mid-life] Heartbreak: A Country Concert

The next date with Song Bird was at a country concert in one of the big casinos on the Strip. We met in the parking garage, then made our way inside, grabbing drinks before finding our seats. She had surprised me by wearing the Lush 3 toy we’d picked out together at the adult store. Setting it up was effortless. As we waited for the performers to emerge, I connected to the device from my phone and began playfully testing the settings. When the headliner took the stage, I tried to match the intensity of the vibrations with the energy of the music. She squirmed beside me, occasionally letting out an involuntary gasp as her eyes rolled back. I smirked, teasing her with different rhythms, and we both laughed at the secret thrill we shared in such a public space. It was exhilarating to know that she had placed that kind of trust in me. Midway through the show, an usher approached us and offered closer seats. We happily accepted, but in the shuffle of gathering our things, something unex...

My First [Midlife] Heartbreak: A Clumsy Question and Classroom Fun

  She and I spent hours talking, drifting from one possibility to the next — things we could do together, adventures waiting to be explored. She was especially excited about trying acro yoga. Her sister had just taken it up and shared photos, which she eagerly showed me. I admitted I wanted to wait until I felt better about my body before I tried it, but the idea intrigued me. The conversation was easy until it wasn’t. In a moment of unfiltered curiosity, I asked her: “Do you think your girlfriends might look at your lifestyle and see your actions as selfish?” The instant the words left my mouth, I knew I’d made a mistake. Her face shifted, her mood dropped. What I intended as an exploration of perspective landed as an accusation. To her, it sounded like I was calling her selfish. The sting was amplified because someone else she had dated had asked her almost the exact same thing — a wound still fresh. What followed was an hour-long conflict, circling around that one word. ...

My First [Mid-Life] Heartbreak: Navigating Boundaries

Navigating Boundaries Ethical non-monogamy can be rewarding, but it is not simple. The lifestyle requires a significant amount of care for everyone involved. Feelings of hurt can be easily triggered—whether through past wounds, oversharing (as Song Bird calls it), straying out of one’s lane, or crossing boundaries. This is not for the faint of heart. Even for those who have practiced it for years, it remains a delicate dance. On our sixth night together, we began with sushi at 8:30 PM. The chef surprised us with a heart-shaped roll that made her smile, and her joy in that moment lit something in me. Over dinner we traded more stories from our past relationships, conversations that pulled us deeper into each other’s histories, our scars and our hopes. By 10 PM, we were still talking, reluctant to move. Afterward, we ventured to a Bachata dance mixer in Chinatown. She was in her element—hips and feet moving with natural grace, her smile radiant and contagious. Watching her dance, I felt ...