After leaving the Philippines once, blaming the country for my mistakes, and eventually returning, I finally learned the difference between unrealistic expectations and reality—and why I’m staying. The Philippines didn’t fail me. I simply learned what it was—and what it wasn’t.
This article is part of the My Philippines Retirement Hub , a collection of observations, practical advice, and hard-earned lessons about retiring and living in the Philippines.
When I first came to the Philippines, I didn’t have the benefit of hundreds of YouTube videos, Facebook groups, blogs, or AI tools explaining the pros and cons of retiring here. There were no endless discussions about the cost of living, healthcare, visas, exchange rates, traffic, dating, scammers, or which islands were best for retirees.
The truth is, I came here cold.
And if I’m being honest, I didn’t come here because I had spent years researching retirement overseas. I came because I was lonely, and American women my age simply didn’t appeal to me. Back then, there were dating sites like Cebuana.com where you could meet online and chat with younger, exotic and beautiful Filipinas, and like many men before me, I decided to take a chance.
Was that a smart plan?
Probably not.
And yes, I made mistakes. Some of them were very costly.
But I didn’t give up, because even after the mistakes, I could see that this was a place where I could be happy if I learned to play the game a little smarter.
The Philippines is not the United States, and it never will be. But it can be paradise—if you make the right choices and arrive with realistic expectations.
Today, you have resources I never had back in 2010. You can watch videos, read blogs, join Facebook groups, ask AI questions, and research virtually every aspect of life in the Philippines before you ever step on a plane.
Use those resources.
Learn first.
Decide wisely.
I may have come here cold in 2010.
Today, you don’t have to.
And that’s one of the reasons why I’m not fleeing the Philippines.
The First Time I Left the Philippines
But I need to be honest here.
I did flee the Philippines once.
In 2016, after four years living in Cebu City, I reached the point where I felt I had to leave for my own emotional well-being. I left behind a house I had been talked into buying (I had to put it in her name, a foreigner cannot own property in the PI), a car, and a household full of possessions I had purchased to make myself comfortable. More importantly, I walked away from what had become a deeply unhappy relationship with a woman I later discovered was still legally married.
Had I known before moving in with her that she was what expats now call a W.I.N.O.—a “Wife In Name Only”—I would like to believe I would have made a very different decision. In the Philippines, where there is no divorce for most Filipinos, a person can be separated for years, even decades, and still be legally married. Understanding that one fact alone could have saved me a tremendous amount of heartache. (See my post on W.I.N.O.s. in the Philippines)
At the time, though, I didn’t blame myself and I really liked her.
I blamed the Philippines.
I convinced myself that the country had somehow failed me, when in reality I had been too trusting, too naive, and too willing to believe what I wanted to believe. I returned to the United States determined to put the Philippines behind me forever.
This time, I met a woman living in Angeles City on the island of Luzon. Before I ever got on a plane, I made certain to ask the question I had failed to ask the first time:
“Have you ever been married?”
After receiving assurances that she had not, I decided to return to the Philippines and meet her.
To make a long story short, we hit it off.
After spending two months together at her place in Angeles City, I returned to the United States and we began planning a future together. The plan was for her to come to America on a K-1 fiancée visa, which allows a foreign fiancée to enter the United States and gives the couple 90 days to decide whether to marry or for the fiancée to return home.
At the time, I believed I had finally gotten it right.
Looking back now, I realize that what had changed wasn’t the Philippines.
It was me.
What Changed Wasn’t the Philippines
I had learned some painful lessons the first time around. I asked better questions. I paid more attention. I was less willing to believe fairy tales and more willing to accept reality.
And that’s when I finally began to understand something that many expats never do:
The Philippines doesn’t fail people.
One of the biggest mistakes Americans make is arriving with expectations that don’t match reality, which is why understanding How to Live Peacefully in the Philippines is so important.
People fail because they arrive with unrealistic expectations, bad information, wishful thinking, or no plan at all.
That realization changed everything for me.
Finding Puerto Galera
We married in Las Vegas and settled into a home in Phoenix, Arizona. And for five years, we were very happy.
Unfortunately, after she obtained U.S. citizenship, our relationship began to change. She became increasingly withdrawn, spending most of her time on Facebook and less and less time with me.
I remember thinking:
Well, here we go again.
By the seventh year of our marriage, we divorced, and I found myself facing a decision that many older people eventually confront:
Was I going to spend the rest of my life alone?
I decided the answer was no.
I still believed that happiness was possible. I still believed I could find the right companion and enjoy whatever years I had left. By then I was approaching seventy-five and felt that time was no longer something I could afford to waste.
Around that time, a friend of mine who had been traveling to the Philippines for many years—and who had a wife and family there—told me about a place called Puerto Galera on the island of Mindoro.
He explained that a close friend of his had recently passed away. The man had lived in Puerto Galera for years with a Filipina companion he had never legally married, and together they had raised two children in a beautiful home high on a mountainside overlooking the ocean.
In January 2025, we traveled to the Philippines together. My friend went to visit his family in Pampanga, while I traveled to Kabankalan on Negros Island to meet a woman I had been talking with online.
After spending ten days with her and her two young children, we discussed the possibility of building a life together and relocating to Dumaguete.
When I returned to Manila to meet my friend after his family visit, he suggested that I meet the woman his late friend had left behind.
He was quick to point out that he wasn’t introducing her as a romantic prospect.
Instead, he described her as someone who might simply be able to help me.
He told me she was forty-six years old, a licensed caregiver, intelligent, well-spoken, and someone he trusted completely.
So we met.
And we hit it off immediately.
She was still living in the large house her companion had built on the mountain. Through circumstances I won’t go into here, she had managed to secure ownership of the property, but after her partner’s death she had very little income.
After visiting her home and spending time with her and her sister, I realized that perhaps we could help each other.
I offered to pay a generous rent.
She accepted.
I then called the woman in Kabankalan and explained that I had decided to settle in Puerto Galera instead.
In May of 2025, I moved to Puerto Galera.
And I’ve been happy ever since.
Why Puerto Galera Works for Me
This place is unique—even by Philippine standards.
It’s safe.
It’s peaceful.
I have fresh mountain air, spectacular ocean views from my veranda, white sand beaches nearby, crystal-clear water, and none of the constant traffic, congestion, or noise that made life in larger cities exhausting.
I have the comforts I want:
- air conditioning,
- a swimming pool,
- reliable internet,
- hot water,
- familiar groceries,
- excellent restaurants,
- good friends,
- and access to healthcare.
I didn’t come to the Philippines to suffer.
I came here to live well.
One of the biggest mistakes many expats make is assuming that retirement in the Philippines means enduring inconvenience as some sort of badge of authenticity.
I disagree.
There are countless beautiful barangays throughout the Philippines where you can live peacefully, safely, and comfortably without fighting the traffic of Manila or Cebu City every day.
And yes, I’ll admit one more thing.
At my age, having people around me who genuinely care about my well-being matters.
The women who help care for me happen to be trained caregivers.
And after spending years in both America and the Philippines, I’ve come to believe there’s a reason Filipinas have such a strong reputation as nurses and caregivers throughout the world:
They care.
And at this stage of life, that counts for a lot.
Why Some Expats Don’t Make It
Now, about those guys who didn’t stick it out.
After living in the Philippines for many years, I’ve watched a lot of expats come and go. Some found happiness and stayed. Others packed their bags and headed back home, often angry, broke, or blaming everyone but themselves.
In my experience, most of the failures weren’t caused by the Philippines.
They were caused by poor planning.
Many of the men who didn’t make it here arrived with unrealistic expectations and inadequate finances. They were young enough to chase a pretty Filipina but didn’t have the income to support either her or themselves. They had no pension, no retirement savings, no military disability, and no real safety net. Their retirement plan consisted mostly of wishful thinking and advice from strangers on the internet.
Then, when the dollar dropped a peso or two against the Philippine peso, they reacted as if civilization itself was collapsing.
My advice?
Be patient.
Come here when you have reliable income:
- Social Security,
- military retirement,
- VA disability,
- a private pension,
- or sufficient savings.
Yes, that may mean you’re older.
So what?
The Biggest Mistakes Expats Make
Then there’s the bad advice industry.
You’ll hear people tell you:
“Don’t worry, just start a YouTube channel.“
“Become a blogger.”
“You’ll make money online.”
Maybe.
But probably not.
As I’ve written elsewhere, making a real living online is much harder than most people imagine. Without a serious plan, trying to fund your retirement through blogging or YouTube is a bit like building a nipa hut out of balsa wood and hoping it survives a typhoon.
Then there are the business dreamers.
Every year, foreigners arrive convinced they’re going to open the next great American-style restaurant, bar, internet café, or “can’t miss” business venture.
The reality is that foreign ownership laws in the Philippines are complicated, and many businesses end up being placed in the name of a Filipino partner or associate. Sometimes that arrangement works.
Sometimes it doesn’t.
I’ve seen too many foreigners lose everything because they entered into business agreements based on trust rather than legal and financial reality.
The Reality About Relationships
And then there’s romance.
Here’s the part nobody tells you:
When you marry the girl, you often marry the family too.
Family obligations and expectations are one of the least understood aspects of Filipino culture, which I discuss in When You Marry a Filipina: Are You Expected to Support the Whole Family?
That’s not a scam.
That’s the culture.
Family obligations in the Philippines run deep, and if you’re shocked by that reality, then you probably didn’t do enough homework before moving here.
At the same time, I’ve become skeptical of many of the “I got scammed by a Filipina” stories you hear online.
In my observation, a lot of those stories begin the same way:
A man ignores warning signs because he’s attracted to a younger, beautiful woman and convinces himself that this relationship will somehow be different from every other relationship he’s ever had.
When the relationship eventually falls apart, he calls it a scam.
Sometimes it was.
Sometimes it wasn’t.
The truth is that many Filipinas come from backgrounds that most Americans can barely imagine. Poverty, absent fathers, family responsibilities, and financial insecurity shape decisions in ways that can be difficult for Westerners to understand.
The way age differences are viewed in the Philippines versus America often surprises Western men. I discuss this in Age Gaps, Foreign Boyfriends, and Chismis.
That doesn’t excuse dishonesty.
But it does explain why survival, family support, and financial security often play a much larger role in relationships here than many foreigners expect.
If you really want to understand how Filipinas think about relationships, family, and foreign men, I recommend watching the work of The Filipina Pea on YouTube. She offers practical, straightforward advice from the Filipina perspective, without the clickbait, fantasy, or nonsense that dominates so much expat content online.
And if you’re thinking about moving here, listening to that perspective may save you a lot of money—and a lot of heartache.
Here’s another gem for the insecure: if hearing Tagalog (or Cebuano, Ilocano, etc.) around you makes you think people are talking about you, you’re going to be miserable. Most of the time they’re chatting about lunch, kids, or neighbor gossip. If that rattles you, you didn’t prepare.
And social media jealousy? Filipinas live on Facebook and Messenger. It’s family, friends, group chats—the daily heartbeat. If seeing your lady glued to her phone makes you spiral, you are in deep trouble. That’s not a bug in the culture; it’s a feature. Accept it or don’t come.
What I Wish I Had Known Before Moving
It all circles back to one thing: do your homework.
- Do your homework about where you’ll live.
- Do your homework about money (pension, savings, income from back home).
- Do your homework about law & business (you won’t legally work or own the thing you think you will).
- Do your homework about your partner (and her family).
- Do your homework about culture (language, phones, family obligations)
- Think twice about driving anything here, even a motorcycle. If you hit someone or even if they hit you, guess who pays? For the price of a car you can get a lot of trike or tuk tuk rides.
- Don’t fear the Reaper – the Philippines is not the dangerous place the uninformed would have you believe. Behave yourself and you will be fine, and travel no further south than Davao on Mindinao.
- Don’t panic at the first sign of chest pains or a cold, they have the best doctors in the world here AND healthcare costs only a fraction of what a doctors visit or a hospital stay in the US will cost you.
- Pay attention to the visa requirements here. You can get by on a tourist visa for a couple of years of extending by a month or two at a time and if you plan to live here permanently the best deal for that is for veterans, the SRRV Special Retirement
- Speaking of Veterans, there is an VA outpatient clinic in Manila where you can schedule video calls with questions about benefits or you can make an in person visit with an appointment but you don’t get the same healthcare here as in the US. You can only be treated for service connected disabilities such as mental health for PTSD. A 100% rating with unemployability means nothing here. As far as being re-imbursed for medical expenses you incur, you can try submitting receipts to the VA and see what happens. Healthcare is so cheap here I don’t even bother.
- Don’t sweat the “skin tax” the difference between what a Filipino would pay for goods or services and the extra $ of what they would charge a “rich” foreigner. Don’t be a cheap charlie and cross the street to save a couple of pesos.
- About dating sites such as the Filipina Cupid, my advice is don’t go there. There are plenty of ladies to meet once you get here, enough said.
Ignore real advice and only listen to what you want to hear, and you’ll be the next guy uploading a “Why I Fled the Philippines” video.
Me? I burned the ship. I committed. That’s why I’m still here—happy, secure, and living the life I chose.
Why I’m Still Here
I didn’t stay in the Philippines because everything here is perfect.
One final thought
“What if I make a terrible mistake?”
My answer is:
“I did. More than one. And I’m still here.”
Continue Exploring
How Seniors Are Treated: Philippines vs. America
Why many retirees discover that age and experience are viewed differently in the Philippines.
YouTube Is Not Your Retirement Plan
Why social media influencers may not be the best source of retirement advice.
The Ladies of the Philippines
Understanding one of the cultural realities that attracts many expats.
Philippines vs. U.S.: Fiesta vs. Fourth of July
A look at how celebrations reflect deeper cultural differences.
When You Marry a Filipina, Are You Expected to Support the Whole Family?
One of the most important cultural questions many foreign men eventually face.
🏝️ Return to My Philippines Retirement
Continue exploring practical advice, observations, and hard-earned lessons about retiring in the Philippines.
📬 BUNKER NOTICE
The biggest lesson I learned about retiring in the Philippines had nothing to do with visas, money, healthcare, or even relationships.
It was this:
The Philippines doesn’t owe me happiness.
My job was to learn how the country worked, adjust my expectations, and build a life that fit reality instead of fantasy.
Once I did that, everything changed.
Subscribe to The Bunker Briefing for more practical advice, observations, and hard-earned lessons about retiring in the Philippines.