What a Girl Wants
Demurely tucked away on a downtown side street, the intimate Italian restaurant was known to boast the best food around. With low lights and crimson and crème décor, the ambiance was set for romance. Like a gentleman, Mr. Montana pulled out my chair, tucked me into place, and ordered us an impressive bottle of wine. Things began on a high note.
He had flown in from Bozeman for the weekend. Having a career which took him all over the country, a quick jaunt to Seattle for a few days for a first date was not an issue for him. As a former college tour guide, I learned the art of amusing out-of-towners. The thought of hosting a Seattle tourist sounded lovely. Montana orchestrated our Saturday evening while Sunday was all mine.
A cozy table in the middle of the room lent itself to some quiet conversation. Obligingly I gave him the sanitized Reader’s Digest version of my post-widowhood life as I delicately nibbled the first course. “Oh, you’re catnip,” he said, and he took a long draw from his wine glass, his eager eyes locked on mine. “I can’t get enough of you.” Coming from a high-level executive in an exclusive firm, I felt complimented. It had been a while since I road-tested my personality on a date.
By the time the check was delivered, he had informed me of his 5-figure billable rate, his assets, and the various properties he owned across the country. Both he and I held careers in healthcare, and it seemed plausible that we could connect about the changing tides in our fields. Yet every time I parted my lips to reply, he leaned in with another credential, another deal he closed, or another unsolicited piece of private practice advice. My unfinished sentences dissolved between our water glasses.
It reminded me of an experience I had as an undergraduate. I was enrolled in a statistics class alongside a guy I was seeing. Back in the day, math was my strong suit, and I was outperforming him in class. As the weeks went on, so did his frustration as he was swiftly outpaced. With an ego that couldn’t take it, he dropped the class. A familiar odor of fragility began to fill the room. I leaned back into my chair, let Mr. Montana take the floor, and stopped trying to meet him halfway.
“Shall we go?” he offered his elbow in a deliberate, old-fashioned gesture. I slipped my hand into his arm as we stepped out into the cool evening air. We casually sauntered down Front Street in Issaquah, past lit storefronts, window gazing and making small talk. Reflected neon from the wet street gave the evening a surreal edge. It felt novel to be out on a genuine date, sharing an easy evening, but beneath the chivalrous surface, his swagger and polished anecdotes carried an unmistakable air of self-importance.
Inside the playhouse, the dimming house lights brought a welcome reprieve. Once the play began, the stage commanded the room, and his monologue finally stopped. Sitting shoulder-to-shoulder in the dark, we shared genuine laughs at the dialogue on stage. For two hours, the interaction felt uncomplicated simply because neither of us had to fill the silence.
Thankfully dating men in their fifties means that most of them don’t have a lot of steam left past 9:00pm. By the time the final applause faded, his high-octane energy had noticeably wound down. The relentless confidence of dinner gave way to quiet fatigue on the walk back to our cars. It was clear to me that we were mismatched, but because Not-Mister-Right had flown across state lines for the weekend, polite obligation won out over my instinct to call it early. We exchanged a cordial goodnight and confirmed Sunday’s morning pickup time for our Seattle tour. The familiar feeling of “this isn’t going anywhere” settled into my bones as I drove a quiet 45 minutes back home.
Sight-Seeing on Sunday
I admit that I deliberately skipped makeup, pulled on my casual hiking shoes, and grabbed my blue rain jacket with the hole. I had no interest in pretense, and I certainly wasn’t dressing to impress.
“Blue is definitely your color. It makes your eyes pop,” Mr. Montana announced as he hauled himself up into the passenger seat of my F-150. I kept my hands on the wheel, mentally adding a full cab wipe-down to my to-do list the moment he left.
Cruising west across Interstate 90 toward Seattle, he turned sideways in his seat. “Did you know that in most cultures outside of the United States, women marry for protection and provision?”
For the next twenty minutes, he delivered an uninterrupted lecture on economics and anthropology, rattling off statistics as if reading from an invisible slide deck. I kept my eyes fixed on the road, though my eyebrows did plenty of talking. In his worldview, every woman was primarily searching for financial security. He had completely miscalculated his audience, so I interjected.
“Mr. Montana, I need to point out that every time I begin a sentence, you finish it for me and keep talking. You haven’t let me complete a single thought since we left your hotel.”
Instead of being taken aback, he beamed. “You’ve got spirit. I like that in a woman.”
Once we reached the city, maneuvering the truck into a tight curb space became his next spectator sport.
“No backup camera? I’m impressed!”
I felt my jaw tighten, holding back the sharp retort sitting on the tip of my tongue. It was evident that he was only seeing what he wanted to see and I knew I would need to use bluntness to correct his vision.
Seattleites are proud to house the beautiful glass artwork of Dale Chihuly downtown near the Space Needle. Walking under the vibrant towering glass chandeliers at the museum, Mr. Montana barely glanced up. “I’ve seen better than this in Venice,” he scoffed, checking his watch. Without hesitation or conversation, I turned towards the exit and headed for the market.
We sampled warm masala chai and browsed the handcrafted leather goods lining the stalls. As we walked, he launched into another lecture: “Did you know that women marry up to improve their status and men marry down?”
Knowing my own family background of generational wealth while he assumed I needed a financial elevator, I walked up to a vendor and bought a $400 piece of artwork on my own card. He watched with wide eyes, quickly pulling out his wallet to offer payment, but I politely declined. “Could you carry this for me please?” I asked, knowing he needed a handkerchief to pick up.
With several hours before his flight, I knew I had to draw things out a bit, so I drove us onto the ferry from Seattle to Bremerton. Inside the passenger cabin, I sat directly across from him with my arms crossed, letting him fill the space. Leaning forward in his seat, he launched into a post-mortem of his recent dating app encounters, remarking on how refreshing it was to finally be with a woman who was “confident yet humble.”
He casually recounted his most recent dates. One woman excused herself to the restroom during lunch and vanished out the side door, while another showed up at a cafe, took the coffee he purchased for her, and promptly walked out. My thought bubble was so swollen that I thought for certain it was going to burst. His utter lack of self-awareness was staggering. The cool marine air helped keep my tell-tale red flush at bay.
From Bremerton, I drove south to Gig Harbor. Looking out over the bay he proclaimed, “This would be an ideal place to retire. Do you like it here?”
“I can’t envision it,” I replied, silently doing the mental math of four more hours to whittle away. “Do you like seafood?” I asked, steering us towards a quaint restaurant on the waterfront. My quiet hope was that having food in his mouth might slow down his commentary.
At our table overlooking the marina, gulls drifted overhead while he leaned in. “Did you know that on these dating sites, there are women in their early twenties who ‘date’ men and see them once a month in exchange for college tuition? It’s kind of like ‘Pretty Woman.’ Women love that movie.”
I set my spoon down, suddenly unable to choke down another bite of clam chowder, which, naturally, he paid for.
“Where would you want to retire if life had no constraints?” he asked, sopping up his bowl with a piece of sourdough. “I’d love to make your dream come true.” Looking at him across the table, I wondered if that meant he knew an amazing disappearing trick.
“And I’ll set you up with a counseling practice where you can host other therapists under you,” he continued. “You can work as much or as little as you want and make ten times what you make now.”
I dabbed my lips with my cloth napkin and slowly folded it across my lap, imagining it as a personal restraining device he was very fortunate I was wearing. He sat back, smiling like an angel investor waiting for me to sign the term sheet. The offer to bankroll my career felt far less like courtship and entirely like a corporate buyout.
There are some things money simply cannot buy.
So Long, Farewell
The drive toward the airport wasn’t awkward for him at all. He remained comfortably engrossed in a monologue of his own making. My role had been reduced to that of an unpaid shuttle driver.
I pulled up to the very first departure curb at Sea-Tac and shifted firmly into park. As he stepped out onto the pavement, the truck’s suspension visibly lifted, mirroring my own relief. The Sound of Music’s tune of “So Long, Farewell” played in the soundtrack in my mind.
“Aren’t you going to get out of the truck and give me a hug goodbye?” he asked through the passenger door. Again, too nice for my own good, I acquiesced. I stepped out onto the curb, offered an obligatory, sideways half-hug, and wished him safe travels on his journey.
The moment I pulled into my driveway back home, the Clorox wipes came out for the passenger side of the cab. The following morning, I sent a brief text thanking him for the weekend and letting him know we weren’t a match. I left it at that, but I was sorely tempted to tell him he might have better luck in Venice.
Post-Menopausal Values Shift
There is a documented shift in how women approach relationships after fifty and through the transition of menopause.
When the reproductive years end, the traditional social scripts expire with them.
In a culture obsessed with youth and physical perfection, women over fifty often face a sudden, strange invisibility. If you doubt that, just watch the flow of cars in a grocery store parking lot on a busy Sunday afternoon. Notice who drivers readily stop for, and who they overlook in the crosswalk. Social validation isn’t automatically handed to mature women. Self-worth has to be generated from within.
When a woman grounds her value in her own personhood and capability, the entire relational dynamic changes. She’s no longer looking for a partner to protect or provide for her out of financial necessity or domestic survival. Her independence fundamentally alters interpersonal dependency and attachment. The motivation for dating shifts entirely away from finding a provider or a benefactor to a much simpler, uncompromising standard: genuine companionship, mutual respect, and two whole people meeting as equals.
If You Want to Know What I Want…
For me, I want a friend. A best friend.
Someone I can laugh with and share genuine conversations with - an authentic space where both of our thoughts, opinions, and stories have meaning. I want to feel safe expressing who I am and offer that same respect in return. The man who loves me won’t ever ask me to shrink myself for his ego. He won’t even entertain the thought.
For me, it’s not about money, or status, or an adult version of show-and-tell. I don’t need Paris or a gondola ride in Venice. My heart would melt over a thoughtful bouquet of roadside wildflowers and a hand reaching for mine as the sun rises. Arms wrapped around me in an unexpected hug, the quiet certainty that he respects and loves me exactly as I am. That is all I’m hoping for.
For me, love lives in the small, everyday ways we exchange affection. And for every day that I am blessed to share with him, I will make sure he understands deep down into the marrow of his bones that he is completely and unequivocally loved.
