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. I apologized, trying to explain that I hadn’t meant to hurt her. My intention wasn’t to criticize but to understand how others might perceive her choices. Still, my delivery was clumsy, and the damage was done.

I told her plainly: it was a dumb question to ask, especially knowing her history with that word. I reassured her that there was no malice in me, no judgment. She eventually seemed to accept my apology, though I left the conversation with an uneasy feeling.

Later, when we spoke again, she admitted she was still upset, still interpreting the question as a sucker punch. I apologized a second time, but she grew more frustrated, even suggesting that ChatGPT was more self-aware than I am. That stung — partly because I disagreed, but mostly because it revealed just how shaken her trust felt in that moment.

I left those conversations frustrated with myself, perplexed by her lingering hurt, yet also more aware. I realized that in this fragile and complex arrangement, words carry more weight than I sometimes appreciate. A single misplaced question can echo like an accusation.

And so, I resolved to learn — not just to speak more carefully, but to listen more deeply, especially when the conversation cuts close to her heart.  While we both intended to ensure our time was light and fun, my interest in her was becoming something deeper than I think either of us originally intended.  Three days transpired into nearly 12 hours of conversation—I doted over her stories, and there was a longing to feel each other and know one another more deeply.  We discussed how there were certain boundaries that we were crossing by having more frequent communication that he would likely consider invasive and distracting to their day to day family life.  Even so we didn’t intend on conversations lasting as long as they did.  We both rationalized that any secret communications resulting in any potential or actual crossing of boundaries was done to clarify expectations or prevent potential trauma triggers.

We were drawn close together by a magnetic-like force of mutual desire and curiosity—where the reality of time occasionally became out of reach.  I began seeking deeper emotional connection with her and encouraged her to reciprocate—my need for nurture and affection was filled by her as I met her need for affirmation.

On our eight date, I picked her up just after 7pm. She stepped out looking radiant, and in that instant the tingling rush in my face reminded me of being a teenager again, falling head over heels for my high school sweetheart. At thirty-nine, I still hadn’t lost the helpless romantic streak I carried at eighteen.

On the drive, we talked about my habit of promising little gestures — flowers, Wagyu beef, guitar exercises — and then forgetting to follow through. She teased me about it, but carried a tone of grace and care.

Dinner at 888 Japanese Barbecue was lively, maybe too lively; the noise made conversation difficult, but we managed. The beef carpaccio and tuna poke were my favorites, while she savored the short ribs and snow crab. She read parts of my journal, chuckling at my reflections and even calling me out on my overestimates of our time in bed. Her laughter put me at ease, but more than that, her reaction told me she understood my heart. Sharing the journal had been a risk, yet it solidified for both of us that I knew my role in this unusual arrangement.

After dinner we headed to a burlesque-rock show. Neither of us expected that I’d be pulled on stage, fitted with a dunce cap, and made the star of a playful detention scene. The “teacher” stripped piece by piece, dancing provocatively while the crowd howled with laughter. I was spanked, teased, and thoroughly embarrassed — and we loved every second of it. The whole spectacle was outrageous, unforgettable.

Later that night, at an adult store, we picked out a high-tech adult toy together — a Wi-Fi and Bluetooth vibrator that synced to music. It felt like opening a door to a new kind of adventure with her, equal parts laughter, curiosity, and intimacy. Back at her casita, we set it up and marveled at its capabilities, already plotting how we might test it on future dates.

That night, I finally met her primary partner. The moment was brief — a handshake, a quick apology for crossing boundaries weeks before, and his gracious dismissal of it. His presence struck me. There was kindness in his eyes, though I sensed awkwardness too. What he does, what he allows for her, requires strength and courage. I walked away respecting him, hoping one day we might be friends.

By the time I said goodnight and headed to South Point for a few quiet hours alone, I carried with me the thrill of the evening — the laughter, the stage lights, the taste of tuna poke, my journal in her hands, and the simple truth that I am unequivocally smitten with this woman.