Ode to a Gen-Z Situationship

Navigating Modern Dating: An Unexpected Connection

In the crowded atmosphere of an Abba-themed dance event, I encountered Jacob. Adorned with a faux-fur head wrap, his youthful appearance was immediately apparent. At 33, I initially hesitated, yet I couldn’t deny his charm. Our eyes met on the patio designated for smokers, and I sensed a shared spark.

Initial Encounters and Lingering Questions

Our conversation began easily. Jacob mentioned he worked “in music,” which I assumed meant he occasionally played guitar. When he inquired about my profession, I deflected, unwilling to discuss work at that moment.

The Shadow of a Recent Breakup

Just a week prior, my former partner had moved out of our shared apartment. After a six-year relationship, his words, “Anna, I don’t think this is viable,” abruptly ended our life together. The relationship’s end was due to numerous factors, including frequent disagreements, differing perspectives on family planning, and a decline in physical intimacy.

Seeking Solace and a New Beginning

Couple’s therapy had improved our communication but failed to rekindle our emotional connection. When he returned his key, I experienced the solitude of my partially empty residence, overcome with sadness.

Unexpected Developments and Shifting Perspectives

With Jacob, my thoughts drifted to my peers who were beginning families and purchasing homes. In contrast, I found myself at an Abba-themed night, consuming a vodka soda, contemplating my life’s trajectory in the realm of modern dating.

He requested my phone number, and I provided it, maintaining modest expectations.

The subsequent day, he proposed meeting for drinks. We opted for margaritas. I arrived ahead of schedule and realized my memory of his face was vague. His youthfulness was the most distinct impression. Waiting at the bar, I pondered his precise age. He eventually arrived, exhibiting Coachella-inspired attire – loose cargo pants and prominent, layered necklaces. I found it somewhat challenging to maintain eye contact.

Age Gap Dynamics

He was 24, nearly ten years younger than me. A wave of self-consciousness washed over me, but Jacob dismissed the age difference.

“Age doesn’t matter,” he asserted.

A statement that, in reality, felt inaccurate.

He revealed his profession as a rapper with successful tracks on Spotify. I was genuinely surprised and somewhat impressed. He mentioned a manager was interested but demanded a substantial portion of his earnings.

Instinctively, I offered counsel, drawing from my experience with predatory contracts as a TV writer. Then, I paused, questioning if I sounded maternal. Our conversation continued, revealing limited common ground, yet I remained intrigued. After finishing our drinks, I suggested relocating to another venue.

Navigating New Territory

The subsequent bar was more upscale. The bartender gave me a peculiar glance. Was I being judged? While nine and a half years might not seem significant, I was now on the opposite side of an age disparity for the first time. In my early twenties, I had dated older men, finding their maturity appealing, but with time, I became doubtful of their motivations. I recalled hearing that complete brain development occurs around age 25. Was my younger self merely vulnerable to manipulation?

Self-Reflection and Shifting Roles

Sitting with Jacob, I contemplated if I was now embodying the role of the older, potentially unsettling figure. I ordered orange wine, and he reacted with confusion. “What’s that?” he questioned.

I explained the wine’s unique characteristic related to grape skins. He nodded abstractedly and then inquired about my current writing projects. I described my horror screenplay centered on a woman losing her sanity in a forest. He listened attentively, his eyes widened, and remarked that it sounded “like a real movie,” which I understood as a compliment.

Intimacy and Connection

Jacob was a tender, albeit slightly apprehensive, romantic partner. He lingered in my living area for an extended period before initiating a kiss. I didn’t mind his reserved approach. He was an adept kisser. And when he gently stroked my arm, the age difference became irrelevant. We were simply two individuals in a bed, seeking to lessen loneliness. Intimacy, for once, felt uncomplicated.

Musical Discoveries and Differing Priorities

On our second date, Jacob shared his musical work. It was characterized by chaos and intensity. Even his voice – deep and assertive – seemed unfamiliar. I struggled to comprehend it.

During our third date, as we lay unclothed in bed, I communicated to Jacob my lack of desire for a committed relationship. I explained my emotional unavailability due to my recent breakup. He concurred, stating it was ideal, as his focus was on his music, not romance. We mutually agreed on a casual arrangement.

Casual Encounters and Growing Disparities

“Casual” translated to weekly meetings. He consistently offered to cover expenses, but I typically handled the bill. My income as a TV writer significantly surpassed his Spotify earnings. He resided in a small studio apartment, sleeping on a futon. I had spent one night there, but the inadequate support caused back discomfort, leading me to resolve against repeating the experience.

Social Circles and Generational Gaps

Two months into our arrangement, we went to a club with his friends in a crowded, humid basement bar where I seemed to be the oldest person present. My attire consisted of high-waisted Zara jeans and a tank top from 2017. The other women sported low-rise pants with minimal crop tops, exuding the self-assurance associated with being on parental health insurance.

One of his friends confided in me about her turbulent relationship. I recommended couples therapy. She reacted as if I had suggested something absurd.

Reflections on Aging and Appearance

The next morning, I meticulously examined my reflection, intensely conscious of forehead lines. I had turned 30 during the initial year of the pandemic. Before the pandemic, I didn’t recall having wrinkles. Post-pandemic, my face seemed considerably older.

Evolving Emotions and Unmet Expectations

After three months, I recognized I was developing feelings for Jacob. On Valentine’s Day, I took him to my preferred sushi establishment. Subsequently, in bed, I expressed my emotions. I clarified that I wasn’t seeking a serious commitment but desired to progress our relationship. Perhaps a weekend getaway?

Confrontation and Disconnection

He became silent. “Perhaps,” he responded with hesitation.

The Breakup and Conflicting Views

During our following date, Jacob ended our relationship. Just after ordering our meals, he abruptly declared, “I think we should scale back our romantic involvement.”

I was confused. Was it about the proposed weekend trip? He replied that it was multifaceted. He didn’t understand my humor, and our interests diverged. Hadn’t we consented to a casual dynamic? Had I failed to recognize his lack of reciprocation when I confessed my developing feelings?

The server returned with our food – a salad for me and macaroni and cheese for Jacob. Awaiting the check, I fought back tears. Dating a 24-year-old in a faux-fur head wrap was one thing; being rejected by him was quite another.

Post-Breakup Reflections and Musical Discovery

That night, sleep evaded me. At 3 a.m., I accessed Spotify and played Jacob’s initial track. I repeatedly listened until the music’s unfamiliarity dissipated. What initially seemed disorganized now resonated with urgency and drive.

I explored Spotify for similar artists. Dating Jacob had apparently broadened my awareness of a new generation of artists creating contemporary music—a realization that was perhaps obvious but one I had overlooked.

Jacob and I had only dated briefly and explored superficial emotional territory. Our relationship was, by definition, a “situationship.” And I had been primarily self-absorbed throughout its duration. Because I often paid, I dictated our activities and dining choices. Furthermore, he appeared consistently impressed by my successful writing career, making me feel accomplished. However, I hadn’t considered his perspective. Perhaps the constant focus on my life made him feel insignificant and adrift.

Moving Forward and Shifting Perspectives

A month later, I reluctantly reactivated dating apps. When I met Jacob, I was emotionally vulnerable from heartbreak. But circumstances had shifted, and I acknowledged future intimate encounters would inevitably generate emotional attachments.

New Connections and Evolving Preferences

I soon matched with Lucas, a 45-year-old with visible wrinkles and graying facial hair. On our second date, he selected an upscale restaurant and ordered orange wine. He had recently purchased a home in Encino and renovated the flooring. After our fourth date, he suggested a weekend trip, possibly to Santa Barbara.

I liked Lucas, but questioned my rapid shift across the age spectrum. Lucas sought a committed relationship. Was I prepared for that? I confided in my therapist about considering ending the relationship. She inquired about my reasoning. I responded, “Because he’s old!”

She chuckled. “If you genuinely like him, that’s all that matters.”

A New Path and Unexpected Reflection

I agreed to the Santa Barbara trip.

One year after my breakup with Jacob, he messaged me. He was now 25, signifying the completion of his brain development, according to some theories. He inquired about meeting up, surprising me. Had he finally realized his dependence on me? He clarified he still desired a casual arrangement but was interested in a no-strings-attached encounter.

I politely refused. Lucas and I had pre-existing plans.