She popped into my connections on Feeld, the open relationship and kink-friendly dating app, with her one photo, clad in a black one-piece bathing suit with most of her face cut off. Her profile mentioned she was looking for a “female mentor.”
Oh, goodness. You have to be fake, I thought, sipping on wine after my kids were in bed.
Sure, on the cusp of 40, I was able to admit the power of my femme fatale vibes as I attracted many younger women with mommy issues. Whether on dates with men or women, I always looked for the telltale sign I had the upper hand: their hands nervously shook when they attempted to take a sip of water. In other words: I’m not your typical suburban housewife and mom.
When my husband and I left organised religion in the middle of the pandemic, we started talking about issues we previously ignored. One of those was our sexual incompatibility. His lower drive had caused frustration in the bedroom, especially as I became more attuned with my body and sensuality without the “pastor’s wife” label.
With this confidence and heightened desire, I finally admitted what I knew since high school: I was bisexual. After doctor visits that revealed no abnormal hormone levels, my husband also came to his own personal sexual conclusion by suggesting he may be asexual, or specifically “grey ace.”
That wasn’t what I wanted to hear, but through many late-night conversations and our preference to stay married, we decided to open our relationship, allowing me to explore a part of myself I kept hidden for a long time.
It wasn’t a big surprise that southeastern Washington State’s queer community wasn’t exactly robust, but I had hoped to connect with people who wanted physical intimacy with a deeper connection instead of an opportunity to fulfil a lifelong fetish or fantasy.
I got bombarded by couples looking for a “unicorn” or third (i.e., a hot bisexual woman). Younger women asked me to dominate and demean them with paddles and derogatory name-calling. I was also contacted by some later-in-life bisexual married women who wanted a “one and done” experience. Let me say, all of that’s fine for others as long as all parties consent and do not feel pressured to participate, but I was looking for something different — a more consistent, meaningful relationship, especially with someone closer to my age.
In the meantime, I wasn’t making worthwhile progress on dating apps, so I scoffed at this latest connection request.
Before dismissing her advance, I zeroed in on this potential protégé’s age: 20.
Yikes, this was too young, I thought. I could be her mom. My kids are closer in age to her than she is to me!
It may have been her bio’s clear intentions (most people tend to be vague), the subtle pic, or my delusional curiosity, but I tapped on the heart before I could find a reason not to.
Like many experimenting women, I figured she wouldn’t respond anyway, and that would save me the time of going through my “Are You Catfishing Me?” litmus test.
Unfortunately/fortunately, she sent me a message telling me how beautiful I was. I thanked her, but swiftly moved into the interrogation. I learned she went to school in Spokane, but lived in the next major city an hour away from me. She was also 6 feet tall and a real life model... or so she said. We were both immigrant’s daughters. I’m Cuban, and her family was from Iraq.
The conversation was so easy and flowed well, unlike most interactions with other 20-somethings I’ve had in the past. I was still cautious yet allowed myself to be flirty.
But my brain was in overdrive:
She’s not really interested. Yes, I’m hot, but do we have enough in common to keep the attraction going?
In what casual ways will she try to pry sensitive information from me like my mother’s maiden name or my high school mascot?
If I meet her, will I get kidnapped and thrown into some human trafficking ring on the other side of the planet for high-wielding elites with a penchant for older women with c-section scars?
My husband thought I was being ridiculous, and then he said it: “You’re too hung up on the age difference.”
And he was right.
I was turning 40 the following month. Though I was overjoyed to have a supportive husband and the opportunity to discover my sensuality and sexuality, I anguished over the lack of direction, wasted time and difficulty I had in finding worthwhile age-appropriate connections. This beautiful girl — I mean, woman — was also incredibly kind and transparent, ready to send pictures, even her professional ones, to verify my concerns and answer my invasive questions. Even so, I was sure it would be a matter of time before she found someone else without arthritis-stricken knees and much perkier breasts to guide her into a world of released inhibitions.
After a few days of back-and-forth banter, I let my responses slow to a trickle, and just hoped she would get bored and find someone closer to her age.
But she persisted.
She regularly checked on me and asked how my day was going. One day she mentioned she was going to her little sister’s class party at school. Upon hearing this sibling was the same age as my daughter, I cringed but suggested we schedule a video chat. She eagerly agreed.
On the night of the chat, I was optimistic but not overly excited. By then, I was a pro at these virtual visits into the lives of potential dates around the Pacific Northwest. I was in pyjamas when we both logged on — anything to give her a reason to bail.
It ended up being one of the best video chats I’ve experienced. Both relaxed in our casual sleepwear, we talked about our immigrant families and how moving away from our faith communities impacted our lives. We shared our favourite heels, and bonded over our love for overpriced clothing at Anthropologie and Pedro Pascal. She mentioned going to casting calls in New York, and I brought up a few of my published creative nonfiction pieces floating around the internet. And, of course, she later read them.
It was the first time I genuinely laughed — abundant snorting and watery eyes — with someone during my mid-life, confusing, attached-but-not-really circus of haphazard non-monogamous dating.
No. No. No. This wasn’t supposed to happen.
I told her I had to cut our now two-hour chat short because I had to pick up my son from a school function. We later messaged each other saying how much we enjoyed the chat with the intention of having another again soon.
Then I heard nothing the next day. Half way into the following day, I sent a low-key, follow-up message. I heard nothing through the next day either, and I couldn’t help it at that point.
Sabotage mode had been initiated.
I started focusing on our age difference. I told myself it was silly that she would be interested. As an Enneagram type eight, I had to cut ties before others did because looking foolish, ill-equipped and betrayed are my greatest fears.
So I disconnected from her on the dating app. I deleted our chat on our messaging app and removed her from my contacts. I returned over and over to my phone as it asked if I was sure I wanted to block her.
Pathetic, I know.
“It’s over,” I told my husband. “It wouldn’t have worked anyway.”
“Maybe she’s busy or lost her phone,” he said.
“Gen Zers never lose their phones!” I said, trying not to sound bitter and unhinged.
And then she reached out. (Yes, I decided not to block her.) She asked about what happened to our message threads since they were gone and vented about her recent school obligations.
And I let it all out. About sabotage mode. Our age difference. My momentary lack of confidence. Most importantly, I apologised.
She was gracious as she asked provoking, concerned questions, and promised she wouldn’t steal my social security number or force me to participate in some gift card scam.
I didn’t deserve her kindness. She showed maturity beyond her years.
Ultimately, it didn’t work out, and our connection fizzled.
But an interesting thing happened. Through that experience, I learned that as people, we are so much more than our ages and generational stereotypes. Last year, even the Pew Research Center announced it would change its study procedures to ensure more caution when using generational labelling and making assumptions based on age.
Kim Parker, director of social trends at Pew, described this better outlook, saying, “By choosing not to use the standard generational labels when they’re not appropriate, we can avoid reinforcing harmful stereotypes or oversimplifying people’s complex lived experiences.”
Online, many of us get our generational know-how from articles and social media posts that exaggerate trends or mock the concerns of certain age groups. I was guilty of this, too, as I’ve found many memes and jokes humorous. But, I had to ask myself, was this information creating thicker walls against potential connection with others in my life?
I started lingering longer when much younger work colleagues were discussing life goals. I invited older coworkers into conversations while also asking about their interests. I encouraged “my people,” older millennials, to tell me more about their lifestyles that were very different from mine.
It may sound trite, but most people just want to feel heard, and I started actively serving as a conduit for people to see me as a safe person to handle their vulnerabilities and dreams without presuppositions. A mid-20s aspiring nail tech who recently left her career path as an educator. A date with a young polyamorous couple who also left church ministry. An empty nester in his 50s working on a futuristic novel he thinks is junk. A grandmother with an overdue travel bucket list at after-school gymnastics. In all of these cases, I’ve been moved by how the human experience connects us, but I had to break the ice and quit being an age snob. And believe me, saying “no thanks” or keeping my earbuds in would have been easier, but think about what I would have missed.
Whenever I meet new people, I want to allow myself to be surprised by the depth of someone’s narrative and their ability to empathise, no matter their birth year. I need to give people the time and opportunity to reveal their authentic selves, which is a fair proposition whether engaging with a date, business associate or neighbour. As I discover who I am on this journey and take comfort in the aging process, I can discern who is worthy of my time or not, but first, I have to let them in.
In regard to dating and the apps promising to offer a plethora of potential life-changing matches, I’m no longer interested in creating a more filtered experience. I’m done with the toggled options, checkboxes and truncating my preferred age range for the sake of “maturity.” Yes, people ghost and get flaky, but I’m now engaging with and meeting individuals of varied age and experience who bring out a delightful paradox: “You’re so different from me, yet so similar.”
And to have the opportunity to experience that odd connection, I am grateful.
Desiree McCullough is a writer in Washington State who enjoys family trips to the Oregon coast, browsing thrift stores for killer heels and bad art, and watching Jeopardy! with a glass of Riesling. Upon completing her Master of Humanities degree in Creative Writing in 2023, she started working on a confessional memoir about her adventures embracing sensuality and sexuality post-ministry. Find out more about her at desireemccullough.com or clavicle.substack.com.