My First [Mid-life] Heartbreak: Our First Date

It’s a warm evening in the suburbs of Las Vegas. The Big Dipper is barely visible against the wash of city lights, and a pale yellow waning gibbous hangs awkwardly in the sky. That moonlight reminds me of how it once canvased her skin at night—the soft stare of her warm brown eyes, her smile contrasted against her dark hair.

An immense joy washes over me when I think of those nights. Her silent, hypnotic gaze seemed to say aloud the words she never could:

“I see you. I feel you. I give all of myself to you in this moment. You fill something in me that I need.”

But then reality sets in. I’m reminded that these moments are only memories—dreams of what has passed and may never come again. The ache that follows is familiar, almost physical. Ahhh, I remember this feeling, I think to myself, recalling my first heartbreak.

I was fourteen. She was a brunette cheerleader with blue eyes, short and beautiful. She was the first pretty girl to notice me and tell me so. I felt desired, accepted—like a stud. My chest swelled with joy.

The problem was, I was grossly inexperienced. I smothered her with attention until I’d clearly caught what middle-school legend dubbed “the cheese touch.” At first, there were long phone calls where she whispered, “I wish you were here so we could make out.” I tried to play it cool, but at every chance on the junior high blacktop, I pulled her close. Too close. I was awkward, overeager, and more than once, embarrassingly obvious in my arousal.

She eventually avoided me, mortified, until the inevitable phone call came: “It’s not you, it’s me.” But of course, it was me. Six short weeks that felt like everything to me must have felt like an eternity to her.

Fast forward twenty-five years. I can’t say I didn’t make mistakes again, but this time was different. I wish I could say I lasted longer than twenty-three weeks, but in the context of dating at my age, it’s not much better than that teenage crash-and-burn. Even so, my time with her was life-altering—something beautiful, unique, healing, passionate, volatile, peaceful, affirming, exhilarating, confusing at times, but always unforgettable.

Those moments shifted my perspective on intimacy. They awakened something dormant inside me.

Before I tell her story, context matters. Who I am—what I see—has been shaped by the environment I grew up in, and the belief systems I inherited over thirty-nine years of life.

I was raised Catholic. My father and mother brought us to church, but when life’s challenges weighed heavy on my mother, she sought help outside of religion. Prayer and faith lost their hold. What remained, though, was her insistence on kindness—her steady teaching that we must be considerate of others.

So while my upbringing leaned toward conservatism, I was also planted in middle ground values—enough structure to anchor me, enough openness to keep me curious.

Even with that foundation, I always felt something was missing in my relationships. Sometimes it was me, sometimes it was my partner, but something was never quite whole. After two failed marriages, I found myself lamenting to a close friend that maybe no one person could ever give me everything I needed.

She suggested something I had never considered: ethical non-monogamy. ENM. At first it seemed strange, but I started reading, exploring, considering. Could I find what I’d been missing in a different framework of love?

By February 2025, I made a profile on a dating site. Three weeks later, I matched with her.

Our first date was in March. We connected instantly over shared values and a love of music. I journaled nearly every detail, and when I look back now, those entries bring it all rushing back:

“I met her on Tinder and we connected through mutual interest in karaoke. She’s engaged, with two toddler boys at home. She and her fiancé live an open relationship lifestyle, with boundaries that seem to evolve over time. I only know fragments, but even from that first night, I sensed the complexity. She dressed in a black dress and heels, despite the cold rain. She looked stunning. We ate sushi on Fremont Street, then drifted into the Neonopolis for karaoke. Her first song was ‘Ex’s and O’s.’ Her voice—perfection at best, excellent at her worst. She exudes sexual energy and confidence. Smart, intuitive, calmly energetic. A woman who could be treasured by most men—and women too.”

I drove her home that night, walked her to the door, and kissed her goodnight.

It was the beginning of something beautiful.