An Old Dog Learns New Tricks
I was inspired to write this after reading a story published on Refinery29, entitled “I’m A CEO, 50 & A Former Sugar Daddy — Here’s What I Want You To Know”
It’s a wonderfully vulnerable and authentic piece that I thoroughly enjoyed. So I was amused to see a huge volume of condescending comments in response.
Which I interpreted as saying a whole lot about the commenters and very little about the author. Envy? Projections? Self-righteous indignation? Yes, these and more.
I can relate to much of what the author owned about his dating experience in that article.
Because I dated women half my age (or less) for over a year.
It was tremendous fun, and sexually gratifying. While it lasted. Ultimately, though, things shifted for me.
This is my story.
Confession? I’m sure some will view it that way, and leave me equally nasty comments. Bring it, baby.
I can look back on my experience now and see that it was a necessary development step that led to a deeper experience of profound love.
In 2010, I finalized a divorce and fulfilled a 10-year dream: Retiring and moving to a little village in Mexico. I thought I’d live there forever, since it seemed a paradise that was beautiful, exotic, and incredibly fun.
In 2014 I got a Facebook friend request from a beautiful young girl from the Philippines. I accepted. She started chatting me, and sending photos. We chatted occasionally, sharing stories from our lives. Eventually she suggested she’d like to meet me. I was enamored with her friendliness, her perceived innocence, and her youthful beauty. The idea of meeting appealed to me, too.
I know, I know. These days you’d be absolutely convinced that she was a scammer. But her Facebook profile went back several years with lots of posts and hundreds of selfies with friends. Not exactly a scammer’s profile.
What about the age difference, I asked (since I was probably older than her father). Her response:
Age is just a number.
Which I later learned is more than just a come-on. It’s like a mantra for Filipinas, who frequently partner with older men — Filipinos and foreigners alike. Older age is prized among younger Filipinas, who equate it with maturity, security, and stability. Far preferable as partners to the boys they grew up with, who are usually jobless, and prone to fuck-and-run — often leaving babies behind for the girls to raise with their family.
I decided to travel to the Philippines to spend a week with her on Boracay Island, the dream destination of millions of Filipinas. Why? Boracay was awarded as the Best Island in the World in 2012 by Travel + Leisure magazine.
She mentioned that she didn’t have a bathing suit appropriate for Boracay. Though she lived near the ocean, most of the time she and her friends just wore shorts and t-shirts when playing in the water. So I located a Philippines online shop, picked out an inexpensive but cute bikini and a couple sun dresses, and had them shipped to her home prior to our trip. She was appreciative of my generosity, which affirmed for her that I was a good man.
I was excited to no end by the thought of spending a romantic week on the Best Island in the World with a gorgeous young girl with light brown skin, long, silky black hair, Angela Jolie lips, and big brown eyes. It seemed like a fantasy about to come true.
Our Boracay Trip
We had great fun together. Holding hands, walking around on pure white sand beaches, looking out on an azure blue ocean. Watching the blue sailboats against a backdrop of spectacular sunsets every night while sitting on the beach and sipping beers. Deep kisses and amazing sex every night.
Between the beach walks, sunsets, yummy food, and sex, though, she didn’t talk much. She usually had fairly short and direct answers to my questions about her family, lifestyle, ambitions, and so on. And rarely asked questions of me. She described herself as a simple girl “from the province”, who had never before traveled more than 50 miles from her family home — let alone ridden in an airplane. I found our conversations boring, but that didn’t keep us from fully appreciating this magnificent place we were visiting. Nor from me appreciating her youth and beautiful smiles.
Though we had loads of fun, it was clear that there was no deeper connection. We were from two different cultures, I was perhaps the first foreigner she’d ever met. When we arrived at the Manila airport gate for her to board her flight home I shared that this was goodbye. I wasn’t up for bullshitting her that we might meet again in the future. She was nonplussed, hugged and kissed me goodbye, and walked down the jetway.
I didn’t leave the Philippines right away. I wanted to do some sightseeing — it’s a long way from Mexico and I didn’t know if I’d ever return to the 7,000 islands that make up this amazing country.
I checked into a hotel and loaded up a dating app — Baddoo. I wrote a little profile with a photo, and reached out to several local, attractive girls. I was pleasantly surprised to find that there was no shortage of young women who loved the idea of spending a few days with a “white” foreigner — particularly when they got to go somewhere they’d always dreamed of while I picked up the tab. It was a foregone conclusion that romance and sex were part of the package. They were exotic, young, and lovely. Not stupid.
Nor were they pros. Just young girls who lived with their family, usually in relative poverty, thankful for an opportunity for an exciting escape for a few days from their everyday reality. And the unspoken possibility that they might score a husband and provider.
I met several girls for 3- or 4-day excursions, each of us thoroughly enjoying the experience. Without any attachments. We would go to an aquarium, or a zoo, or an amusement park, or island hopping on a small boat, or snorkeling, or scuba diving, or visiting an outback adventure park with a zipline through the forest or over a lake. There was plenty to do and see, always with a sweet girl on my arm.
It was understood, when we parted, that I would pay for a taxi back to their home. And it was pretty frequent that they’d ask for $20 or so, “just to help them out”. I was happy to oblige. That was a lot of money for them, and manageable for me.
These girls were fun! I felt younger than my years, hanging out with them. Though I’d never thought of myself as a handsome man it seemed they found me as attractive as I found them delightfully pretty, sexy, and lively. It was a great ego trip! Meanwhile, they were creating fun memories, exciting stories, and plenty of selfies in exotic places that they could share with their friends.
Time to go now.
After a month or so in the Philippines, I was ready to head back home. But a friend’s parting words before I left Mexico came to mind: “If you’re going to be in Southeast Asia, you must see Bali”. I booked a flight, figuring I might spend a few days or a week there.
Long story short: I was so blown away by the unique culture, variety of natural beauty, and sacred Balinese Hindu traditions of Bali that I decided to stay there rather than return to Mexico. I found a comfortable place surrounded by the fabulous Ubud rice fields (from Eat Pray Love fame) at a reasonable rental rate, and rented a motorbike to get around.
I had gotten a Visa On Arrival that was good for 30 days and extendable for another 30 — after which I’d have to do a “visa run” out of the country and back in again — which many people did same-day.
I was happy, though, to use visa runs as an excuse to travel to other SE Asia countries for a week or two at a time— Malaysia, Thailand, Singapore, Vietnam… and of course, the Philippines. The latter being the most frequent because of the lovely, English-speaking women and the fun I always had there.
Generally, I’d meet new girls each time I went to the Philippines rather than seeing girls I’d dated earlier. Like the first girl I’d met, these were self-described simple girls, with very little life experience that made for interesting conversation.
Riza was different.
However, I met one lady who was quite different. Riza and I had wonderful conversations, and we saw one another several times over the course of a year. She had a big aspiration: to become one of the millions of Overseas Foreign Workers in the Philippines. Go to another country with a 2-year contract to become a household worker, earning far more than she could expect in her home country — maybe $400/month.
When I departed for Bali after being together for a few days we both were sad, Riza often given to tears. We acknowledged that we were both feeling the onset of love as we chatted nightly. On one level, we were partially open to our relationship continuing to evolve. But I recognized that her prime intention in becoming an OFW was not about the money. It was about the sense of adventure of living in a foreign country — alone, independent, achieving financial success. Making her own way in life, on her terms. I couldn’t allow myself to interfere with her big life plans. Nor was I prepared to put a relationship on hold for two years.
One day she said she had been accepted to a position in Saudi Arabia. I was aghast. Saudi abuse of young, female OFWs — physical and sexual — was well documented. My research showed that they were known to occasionally hold their workers’ passports, so escape from any sort of abuse was impossible prior to contract expiration. There were stories of Saudis withholding their OFWs’ pay rather than paying monthly.
I was scared for her. And scared for my own feelings, should she end up in a cruel work situation there. With nothing at all I could do to rescue her, I could imagine my heart breaking for her. I shared that if she accepted that position I had no desire for ongoing contact. Zero interest in running the risk of helplessness and depression, should the worst come to pass.
Excited as she was at scoring an overseas assignment after months of waiting, she wasn’t ready to trade that off for our relationship. She declined the position — which was a fortunate choice. She later obtained an offer to go to Singapore — a thriving country, nearer to home, and at considerably higher pay than middle eastern countries.
Back to Boracay
While Riza was preparing to go to Singapore, I went back to Boracay Island. I had visited two times since my first visit, once with her. I wanted to explore the possibility of living on Boracay, so I rented a place for a month. Riza wasn’t able to meet me there, as she was fully engaged in doing all the preliminaries to leave the Philippines later that week.
While there, though, I met Joy.
At 36 years, she was the oldest Filipina I had met. The difference in maturity, though, was instantly apparent. She had had a wide variety of life experiences — including several years as an OFW in Iraq, several former heartbreaking relationships, and a serious brush with extreme poverty. On the night we met we talked until 4AM — holding off on our desires to ravish one another because of the quality of our conversation.
She was truly, uniquely fascinating! I quizzed her about her heartbreaks, her family, and experience working overseas. I discovered she’d read The Alchemist by Paolo Coelho — a very meaningful book for me. When she spoke of painful experiences, she neither hid nor apologized for her tears. I admired her willingness to be emotionally vulnerable and wonderfully authentic with me after just a few hours.
She asked me about my life in Bali, my past relationships, and my previous experience dating Filipinas. I shared about the many girls I’d dated. About how I had found most of them fairly immature, given their youth and lack of life experience. I shared about my feelings for Riza, who (as I’ve said) was different. My disappointment that she was off to Singapore within a week, and that our relationship was, out of necessity, coming to an end.
We bonded in a way that I had not before with a Filipina. There was a chemistry quickly developing between us.
In the days that followed we played together as we explored areas of Boracay Island that were new to us both. She climbed coconut trees and rocks in her bikini, posing for photos. We had a few too many drinks on several occasions. During one such time we came upon a climbing wall. She was clearly feeling her alcohol, and wanted to climb to the top and ring the bell. “Not likely”, I thought.
“Hold my beer”, was her sentiment.
A woman of substance.
Clearly, Joy was not just another pretty face. When she returned to Manila to celebrate Christmas with her family, we agreed to meet there for New Year’s Eve. My one-month Boracay rental was about to come to an end, and there was no doubt we wanted to see each other again.
While we enjoyed a NY Eve fireworks display I invited her to come back to Bali with me. She agreed joyfully, without hesitating.
We flew to Bali together — both of us by this time clearly feeling a deep connection. What followed was 30 days of fun exploring the vast island of Bali. I taught her to swim, and snorkel. We went to Pura Besakih — the sacred “Mother Temple” of the Balinese Hindus. To the sacred public baths. To the Gili Islands — one quiet and romantic, the other known for partying.
The Sacred River
Our most memorable Bali experience was while walking around the Ubud rice fields, hand in hand. We came upon one of the many Balinese artists who maintain little sheds on the path, offering their artwork for sale. Perhaps sensing something special between us, he offered to take us to the sacred river. It was a downhill walk on the other side of the rice fields, he told us. He would guide us there, and then leave us to enjoy it privately. (Hint hint). He introduced himself as Gusti.
He led us to a steep unmarked path down the side of a heavily wooded gorge. Gusti could see I was a bit tentative about walking down such a steep path, partially because I was nursing a bruised hip from a fall the day before. “Careful, grandfather”, he said (a very honorable title), and took my hand to steady me as we walked downward on a path he may have hiked hundreds of times before. Meantime, Joy had kicked off her shoes and was practically skipping down the path. “I’m a mountain girl!”, she declared proudly (which I’ve come to hear as explanation for anything unusual she does).
The river was breathtaking. Only maybe 30 feet wide, with huge bamboo trees and coconut palms growing up both sides of the steep gorge. Gusti said we should be able to find our own way back up, and left us in this private, amazing, picturesque natural scenery.
We quickly doffed our clothes and waded into the swift-running but shallow river. The Balinese regard their rivers — and water itself — as sacred. Bathing in rivers is said to allow it to refresh the soul as well as the body. We thoroughly enjoyed that experience of being nude in the cool, flowing waters of our own private, sacred sanctuary.
After a while we got out and put our clothes on again. Shortly thereafter, Gusti reappeared. His mother, he said, had instructed him to bring us back up so we didn’t get lost. But before that he invited us to pray with him to Mother River, as thanks for our time there. He invited us to do a call-and-respond prayer, which was beautiful. When I asked him if he was a Hindu priest, he affirmed that yes, he was.
Then the magic began.
He asked the two of us to stand face to face, foreheads together with our arms around one another. He asked if he could put his hands on us and offer a blessing. We trusted this fascinating man, and agreed. He began rubbing our backs just behind our hearts in a circular motion, while reciting a prayer in Balinese. Though we had no clue what he was praying for, it felt to both of us almost like a wedding ceremony — very sacred.
At the conclusion of this we thanked him and said we were ready to leave. As he led us back up the almost-trail he offered me his hand. I noticed that my hip no longer hurt — all the pain from the previous day’s fall had dissipated. Was it from bathing in the sacred river? Gusti’s blessing? I didn’t know, but it seemed near-miraculous. I didn’t need his support to confidently scale the steep slope.
When we arrived at his hut we viewed some of his art offerings. Joy bought a piece that attracted her. We thanked him again, and I gifted him some money for his guide offering and blessings. We walked away, hand in hand — feeling as if we had just experienced something sacred and magical. After a few minutes walking I stopped, pulled Joy close to me, and said for the first time “I love you”. She returned that precious phrase. It was entirely spontaneous and unexpected, and marked a precious moment in time from which there was no turning back.
Joy’s return to the Philippines
After 30 days of fun, travel, and exploring this newfound love together, we both understood it as a beginning rather than an ending. Joy was unable to remain in Bali for family reasons. So I decided to join her in the Philippines 30 days later.
In December 2020 we celebrated our fifth anniversary of meeting in Boracay. I prepared a delicious dinner of Tuscan Chicken and a nice Chardonnay. We ate it by candlelight beneath a flowering, Christmas-decorated tree just outside our home.
I have come to admire and adore this amazing, fun-loving, humorous, and persistently happy woman more than anyone I’ve ever known. We truly enjoy doing just about anything together — hiking, scouting out waterfalls nearby, snorkeling, or just sitting on the couch watching a movie. Our love never seems to get old or stale. We know we’ll spend the rest of our days together. When I’ve passed she can rest assured that she’ll never again brush up against poverty.
We have a wide and growing circle of friends — many of whom are couples like us — older expats and younger women — truly enjoying their lives together. For us men, these young, beautiful, and loving women that are our partners keep us feeling younger and more vibrant than our years.
My self-development process
Dating many young girls was exciting, but after a while the novelty of freely available fun, romance and sex with 20-something beauties began to feel shallow and pointless.
But had I not learned the emptiness of hit-and-run dating, no one would have been able to convey to me how unfulfilling it would become. That experiential unfolding opened me to a desire for a relationship that was more satisfying and profound. Like a tasty, home-cooked meal after a year-long diet of McDonald’s hamburgers and fries.
Then in the moment I was ready, Joy showed up in my life. I’m deeply grateful that all evolved exactly as it did.
Hence, the title of this story — An Old Dog Learns New Tricks.
Oh, about Riza…
After a tearful videocall in which we agreed our relationship had come to an end point, Riza and I said goodbye to one another before she headed off to Singapore. We remained friends and stayed in touch for a while after I had moved to the Philippines with Joy.
She met a wonderful man there, got married, and gave birth to a baby boy about a year ago. She seems supremely happy.
Our brief relationship was but a stepping stone for bigger and better experiences for us both.
And the other girls?
Everyone seemed satisfied that our passing flings were what each of us were seeking. None ever expressed anything beyond appreciation for the brief time we’d spent together.
Thank you for reading my story of sex, love, and self-development.