What Happened When I Agreed To Go On A Date With A Man Decades Younger Than Me

He was far closer in age to my daughters, but he helped me recognise something important about myself.
The author
The author

“So you’re a cougar!” a girlfriend said when I told her about my date with a man young enough to be my son. She was joking, but I still bristled at what I consider to be a derogatory term for women doing what men have long been encouraged to do.

After being married for 20 years, I went through a horrific divorce. By the time I was ready to actively date again, I found the pool of eligible men my age (mid-50s) to be wanting.

Mating calls from the few men I met through friends who offered to cook pasta at their place or bring a bottle of wine to mine didn’t qualify as real dates to me. And no words can adequately describe the wealthy yachtsman who insisted, after buying me one meal, that I allegedly promised to cook him dinner — and do a whole lot more — the following evening.

The men I encountered through online dating were worse. A few blatantly lied about their relationship status or having kids. Most wanted someone considerably younger than me. And don’t get me started on the misogynist who began trashing his female boss the minute we sat down for a drink.

Straight, kind, generous ― was I really asking for too much?

Enter a young pilot I’ll call Ahmed whom I met at Dulles Airport as we waited for the same delayed flight to Savannah, Georgia. After I’d gone to check the flight status at the counter, Ahmed ― tall, dark and handsome ― approached me and asked what I’d been told.

“Mechanical difficulties,” I responded.

“The update they sent me blamed the weather,” he said, showing me the airline’s text.

“They lied,” I said.

Ahmed smiled as we made our way to adjoining seats. He was maybe 30 — far closer in age to my 20-something daughters than me.

It was early evening, and I’d already put in a full day with family before driving two hours in heavy rain and traffic to the airport. I’d had no time to wash my hair or apply makeup and was wearing leggings and a shapeless tunic — the signature outfit I’d been sporting since gaining 20 pounds over the prior two years. I felt I was looking my worst.

Ahmed, on the other hand, was clearly well-toned beneath his tailored jeans and fitted t-shirt and looked fresh despite the series of planes he said he’d already taken that day. I tried not to stare at his muscular arms as I shuddered at the thought of the flab on mine. Still, I noticed him glance at my shoulder tattoo and nod his approval.

“You live in Savannah?” I asked in an attempt to distract him from my arms.

“No,” he said. “I’m from Saudi Arabia.”

He was headed to a town just outside Savannah for his annual flight training. I told him I’d been visiting my mother.

“I’d like to take you for dinner at the Olde Pink House,” he said just before our flight was called. I was surprised by his offer — but agreed.

“Given my shoddy experience with men who ought to have known ― and treated me ― better, what were the odds a stranger from a generation steeped in hookup culture would follow through?”

We exchanged phone numbers but I put little stock in an invitation to one of Savannah’s most expensive and romantic restaurants from a handsome man decades younger than me. Given my shoddy experience with men who ought to have known ― and treated me ― better, what were the odds a stranger from a generation steeped in hookup culture would follow through?

Speaking of the hookup culture, I thought it was odd Ahmed had asked me to dinner in the first place. I thought people his age skipped dating, started the evening with sex and only occasionally reached the point of cohabitation. Still, though divorce had devastated me, I remained a firm believer in love and courtship and despite my hesitation, I thought, why not?

We boarded and headed to our seats at opposite ends of the plane. After we landed, the reality of what I’d done started to sink in and I hurried off to my car.

What had I been thinking giving that young man my number?! Given my age and disheveled state, surely he’d never call. Why continue to indulge my pipe dreams only to be made a fool of when nothing came of them? But later that night he texted to make sure I’d made it home safely.

Still resisting the urge to be drawn into my fantasy, I hopped in my car the next morning and followed through with my previously scheduled plan to attend an out-of-town silent retreat.

“How are you? Hopefully everything is okay,” Ahmed texted me while I was away. “I am waiting for you to come back so I can see you.”

He also asked for my photo (uh oh!) and then texted me a string of his own. I scrolled through them slowly, leery of what might appear but, thankfully, he was no Anthony Weiner.

After I returned home from my retreat, Ahmed suggested a date for our dinner. That evening we spoke at length by phone, something else I didn’t think anyone, much less young people, did anymore.

“When you told me about talking to the gate agent, I said to myself, ‘This woman has principles, which I like in a woman.’”

I consider myself a strong, proactive woman who won’t accept lies from an airline employee, a prospective date or anyone else — so I mentally awarded him a thousand points for how quickly he seemed to understand that about me.

Two evenings later we met at the Olde Pink House. Ahmed called ahead for reservations and asked if I minded pushing the time back so he could shower again after work. How refreshing it was that he seemed to want to put his best foot forward and I thought, Why shouldn’t I? So I spent the next several hours styling my hair, applying makeup and selecting just the right dress and earrings.

Ahmed arrived at the restaurant at the precise time we had agreed to meet. He slid his soft hand over mine as we walked from the lobby to the dining room where the waiter showed us to our table. He continued standing as the server pulled out my chair and only once I was seated did he take his own seat.

The waiter stopped by several times to take our orders, but we were so engrossed in our conversation that we kept forgetting to open our menus.

“How refreshing it was that he seemed to want to put his best foot forward. So I thought, 'Why shouldn’t I?'”

We talked about our jobs ― my writing and his career as a medical pilot who flew patients all over the world to specialized hospitals.

He told me he was 36. I didn’t share my age but it was clear I was much older. Evidently he didn’t care. He said he traveled often and recounted a few stories about the “immature” women that had hit on him ― women he claimed to find tiresome.

We were both divorced with children. I told him about my aging mother, and he told me about his. He said he’d recently moved in with her after his dad and his brother had both died. He felt she could use his help and emotional support and spoke of her in a way I’d never heard a man ― except perhaps my deceased father and grandfather ― revere a woman.

“The restaurant is closing,” our waiter informed us several hours later. We’d been so caught up in our conversation that we hadn’t noticed the room gradually emptying of everyone but us.

“Thank you,” I said as the pilot handed his credit card to the waiter so quickly the bill hadn’t even had a chance to land on the table.

“Of course,” Ahmed replied, with a puzzled look.

I’m usually uncomfortable when the check arrives while I’m on a date with a man my own age. In this world of post-divorce dating, I’m never sure what I’m supposed to do. Considering the strides women have made and the era we’re living in, part of me feels like I’m supposed to reach for the check or offer to go Dutch, while another part of me insists that I remain still and stop trying to find excuses to let my date pay.

To be clear, I don’t need a man to take care of me but I also won’t apologise for my preference for old-fashioned romance and men with initiative.

Outside, Ahmed and I sat on a bench and kissed.

Just before midnight, he reached for my hand and walked me to my car. I drove home in silence, pleasantly dazed by the fact that the dream I’d just experienced had been real.

The next day, we exchanged texts relaying what a “wonderful” night we had had together.

How unexpected that a man decades younger than me had treated me so well when so many — almost all, if I’m being completely honest — of the men my own age that I’d encountered, including my husband, had been so disappointing.

My divorce had transformed me from a strong, confident lawyer and very capable mother of two to an emaciated shell of a woman haunted by fear and self doubt. For years I couldn’t even look squarely at the mirror when I applied makeup ― the displeasure with myself was that powerful.

I had aged. My children had grown up. In the wake of my divorce, I dismantled the contents of the Brooklyn home I could no longer afford. And as I did, there amidst all the clutter and the devastation I had been through, I was astonished to discover the woman I’d once been, the one friends had urged me to reclaim.

I’d spent so many years burdened by my ex-husband’s estimation of me, I’d neglected to embrace what I thought of myself. And now, this date with a young pilot offered me even more of a chance to see myself as I am, but had ignored for much too long: someone who is attractive, interesting, and worthy of spending time with.

“I’d spent so many years burdened by my ex-husband’s estimation of me, I’d neglected to embrace what I thought of myself. And now, this date with a young pilot offered me even more of a chance to see myself as I am, but had ignored for much too long.”

A few days after our date, Ahmed flew home. I never saw or heard from him again. And I am completely okay with that. I knew going into that magical dinner that one date with a man two-thirds my age who lived halfway around the world probably wasn’t going to lead anywhere. But that doesn’t mean the night didn’t mean anything. Quite the contrary, whether or not Ahmed knows it, he gave me a wonderful gift: He recognised my worth and he helped me to recognise it too.

Now, I rarely date. I’ve shuttered my online dating accounts. I rarely encounter eligible men my age, let alone any I believe are worthy of receiving my time and energy. And I’ve realised I don’t need a man to make me happy. Still, I’m wide open to the possibility of a longterm commitment with someone if there’s another man ― of any age ― like Ahmed (who doesn’t live thousands of miles away).

Ultimately, I may not relate to or even like the term “cougar,” but I do embrace the spirit and attitude that it represents. In a world where women are told they’re past their prime once they reach a certain age (which seems to be getting younger and younger), it’s important to value who we are and what we have to offer, and that that is recognised by the men with whom we choose to spend our time ― no matter how old we are or who does or doesn’t invite us out for dinner.

Beverly Willett, an entertainment lawyer turned writer and TEDx speaker, is the author of Disassembly Required: A Memoir of Midlife Resurrection. A longtime resident of New York City, she now lives in Savannah, Georgia.

This article first appeared on HuffPost US Personal

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