The Holiday Girlfriend Who’s Upfront About Money
I started traveling to Thailand about 15 years ago, not having the resources as we do now. I made my share of mistakes. I have many stories from my experiences, but most of them are the usual ones involving bar girls, freelancers, go go girls, tuk tuks, taxis, and massage shops. I have two stories over the years that I find memorable and one that is currently ongoing. I will start with the one that is currently ongoing and work backwards from there. It shows that if both parties are honest and set boundaries, a good non drama girlfriend experience can happen. It does take the right mindset. Having been divorced twice, I’m done with long term relationships. The love of my young adult kids, plus an occasional dating experience, keeps me grounded back home in America.
Meeting Tuk
On one of my trips to Thailand in early 2018, I bar fined a girl in Pattaya. She went by the name of Eureka, and after getting a late night meal, we went back to my hotel and did the obvious aerobics. We had fun, but it was not mind blowing. She ended up spending the night and left after we went another round and had breakfast the next morning. I told her I would see her again and would come by the bar later that night. She told me she would not be there as she had a contract for a few days. She then asked me if I would like to see her friend.
I thought this was a bit odd, and I realized she probably did not like me very much. Knowing this, I hesitated but decided to meet her friend. I gave her my LINE ID and WhatsApp and asked her to have her friend contact me. She explained that her friend worked for an agency, and I would need to contact the agency directly to meet her.
Despite the yellow flag this raised, I went online and made an appointment to meet Eureka’s friend. Her name was Tuk. Her looks really caught my eye, and I wanted to meet her. With some nervousness and hesitation, I booked a date with her. She met me at my hotel and provided her information at reception. I was pleasantly surprised to see that she looked exactly like her pictures. Honestly, I was not expecting that based on previous experiences back in America.
Our time behind closed doors was great, and I asked her if she would spend the night with me. After negotiating a reasonable rate, she agreed but said she needed to deposit the money as that is how they are tracked. I gave her one of my hotel room keys so she could let herself back in without me having to meet her at the elevators. About an hour went by, and I started thinking she was not coming back. However, I noticed she had left her backpack in my room.
Tuk returned about 90 minutes later with a large amount of takeaway food. It was a wonderful spread of seafood, chicken, vegetables, and pork. This was a first for me. Never before had I had a girl buy me a meal. We grabbed some drinks from the overpriced mini bar, which I did not mind, and after eating, I took her up to the rooftop bar for another drink before we turned in for the night. We went another round of aerobics and off to dreamland I went.
Tuk’s First Meeting
I woke up in the morning and we had another round before breakfast. Shortly after breakfast, I had to leave for Bangkok to catch my flight to Phuket. I kept in touch with her through LINE about once or twice a month after returning home to America.
About 9 months later, I found myself heading back to Thailand. I asked Tuk if she would like to spend the night with me, and she asked me to schedule the date through her agency. I booked an overnight date and paid more than I should have, but she was worth it to me.
This pattern continued whenever I visited Thailand.
The Pandemic and Reconnection
Fast forward to March 2020, and my planned trip to Thailand was only 3 days away. I already had an overnight booked with Tuk 4 days before my departure. My neighbor Bobby, who was in the Philippines and planning to meet me in Thailand, messaged me on WhatsApp telling me not to go. He said the Philippines was shutting down and Thailand would be next. He was heading home because he did not want to get stuck. Shortly after that, Tuk messaged me online telling me the same thing and said she was heading back home to Isan.
A few weeks later, I messaged Tuk and got nothing back. A couple of days later, I tried WhatsApp and again nothing. About 3 months later, I sent a simple “Sawasdee krap” through both LINE and WhatsApp and still got no response. By then, I assumed she was with one of her many farang boyfriends or sponsors she probably had I’m not naive. A girl this pretty, fluent in English in her early 30s with a sparkling personality would almost certainly have one or two more sponsors. I did not try to contact her again until late 2021 when Thailand reopened under the vaccination test and go program.
I planned to be in Thailand in March 2022 and thought it would be nice to reconnect with her. I messaged her online and again received nothing. About a month before my departure, I visited the agency website she worked with and was surprised to see her profile still listed. I sent a request to meet her, and to my surprise, she responded the next day and was happy to hear from me. She gave me the usual explanation that she had replaced her phone and lost most of her contacts and had to get a new LINE ID. I did not think much of it and did not really care as she was not my girlfriend and I was not her sponsor.
It was fun being with her again after not seeing her for a couple of years. She had the same energy behind closed doors and always left me short of breath.
The Farm and the Money Requests
Later that year, during one of our random LINE chats, she told me her mother needed help on the farm because her brother was in jail. She said she would be helping her mother and probably would not be working for the agency anymore. I remember thinking to myself, what would she say next? Expecting something along the lines of a sick water buffalo or a broken pickup truck but I did not get either. She simply carried on telling me about their farm, which was not doing very well.
After she moved back in with her mother, we continued to stay in touch through LINE video calls once or twice a month. Her mother is very funny, and somehow between her mother’s almost non existent English and my terrible Thai, we managed to exchange a few basic sentences. Over time, the chats with Tuk become more about her hardships and the farm not making any money. She asked me to help her with money from time to time. It was never a large amount usually between 3,000 and 5,000 baht and I did not mind as we agreed it would go towards my future visits and she would help me learn to read and write and speak Thai. Although I failed miserably at the writing part.
After a while, I grew tired of hearing the same old thing on every call, and I knew it was only a matter of time before I would be pulled into a sponsorship situation. That was not something I wanted. So, apart from a few Buddhist and Thai holidays, I stopped initiating contact.
The 2025 Reunion
In August 2024, my neighbor Bobby asked if I wanted to meet him in Thailand around February 2025. Without hesitation, I said yes. I made my travel plans and decided to contact Tuk. She replied the next day and agreed to meet me in Bangkok, go to Hua Hin, and then spend a few days in Pattaya. As usual, we negotiated a price based on what I had already given her, factoring that into the total. I knowingly broke the 3 day rule this time, but I felt comfortable with my holiday girlfriend arrangement with Tuk. We both enjoyed each other’s company, and in typical Thai girlfriend fashion, she talked me into letting her stay with me for the rest of the 5 days I was in Thailand for a price, of course even though we had originally agreed to 10 days.
While in Pattaya, she had her friends come over to visit, and I paid for a couple of meals for everyone. My neighbor Bobby, who was with me the entire time, was no help at all. I was his entertainment, and he encouraged the girls to spend my money and gave them all the overpriced items from my mini bar. Between their appetites, Bobby and the girls emptying the mini bar as soon as it was restocked, I was starting to run low on my budget.
Luckily, Tuk let me turn the tables, and instead of her owing me, I ended up owing her money this time. I did not mind, as I knew it would only be a matter of time before she asked me for money again. I never tap into funds beyond what I budget unless I absolutely have to and spending time with a girl does not fall into that category.
I am now in the process of finalizing my trip to Thailand in February 2026. Tuk will be accompanying me again for about half the time I’m there. I’m sure her goal will be to talk me into letting her stay with me the entire time like an idiot. It will probably happen.
This story is still ongoing, so I will wrap it up there. Although Tuk denies having any boyfriends or sponsors, she openly admits her lifestyle as a girl for hire. Her mother worked in a massage shop in Krabi years ago. So maybe like mother, like daughter. She is different in the sense that she tells me upfront in a polite and honest way that everything between her and me is about money.
Story Two: The Real Thailand Understanding the Culture Behind the Smile
Thailand is a big, beautiful, safe, warm country. Many of its women are beautiful, too. I moved here from the US when I was 63. That was 2 and a half years ago. Thailand can teach you a lot about yourself, but you’re going to think it’s about the girls. You lived in a very different culture before you got here.
Whether you’re an expert or a vacationer, that makes it hard to separate flirtation from culture. Thais even toddlers are taught to show respect to older people. When I say older, a 20 year old Thai bar girl will address her 22 year old coworker as ‘P’. ‘P’ basically means older sister, and she’ll do this out of respect as her coworker is older than her. Long before you got here, the default social posture was respect. Even during brutal boxing matches, the combatants are constantly touching gloves and wai ing each other. After the bout, they hug like siblings, both bloodied. The language even has a polite modifier ‘ka’ or ‘krap’ to soften the end of a sentence. It’s soft and impolite to say ‘no’ here. So Thais say ‘mai chai’ (no/yes).
The Face Factor
How does all this affect dating and help you find a normal girlfriend? It complicates it. So does the overlapping elephant in the room face. When you see those girls in banks, juristic offices, clothing stores, and real estate offices, they see 55 year old men while their supervisor is 8 feet away. You’re encountering them in tourist cities, in service industries. So, out of respect, they soften their voices, duck when walking in front of you, scamper to your table to serve you, and aren’t confrontational. You will often make the mistake that this is either romantic interest when in fact, they treat 50 year old Thai men the same way.
The gestures you sometimes assume are flirtatious are them doing their job well in a very face based society and are also done by men in the same jobs. You just don’t notice it when the condo security guards and hotel front desk guys do it. Plus, you’re around way more women than men barber shops, restaurants, baht buses, and massage parlors.
The other misconception is that all these single women divorced unfaithful Thai men to become eligible to date farang, or that they’re all dying to meet expats and be finally saved by you. If that were the case, how did 71 million Thais get born? Who do single Thai men date? Very few Thai women have ever dated a Western man.
But if you have alcohol issues, or fetishize Asian women, or move here without hobbies or remote responsibilities, this isn’t a good fit. You’re going to find hours of free time a day, cheap beer, and human girls with complex priorities. Geography, distance, families including their parents and their own children are more years ahead of them than behind you.
The safety and respect and recognition of seniority here is a beautiful thing if you take it for what it is and don’t assume you’re here to save anyone. Use the year round warm weather, low cost food, and lovely view from your condo balcony to save yourself your pension, your health as you age, and your sanity. If you prioritize that, just like Thai women think survival and family first, the dating and the relationships will take care of themselves organically not from thirst, depression, fantasy, or escapism from the West.
Understanding the Face Factor
The best, most genuine women like to be seen as a companion, not an escape hatch just like you want to be seen as a lover, not as an ATM machine.
Story Three: The Department Store Mystery A Cultural Misunderstanding
Back in Bangkok after 6 years, I stayed for a week, but it was more or less impossible to have a serious conversation with people there because they are not used to speaking English. I was very happy when I met a young sales assistant in a department store who had studied my language from my home country.
She was a young girl with skin problems on her face, but the fact that she spoke my mother language at university level made everything else irrelevant. She helped me place an online order through the department store for a shirt that could only be ordered online. The next day, I returned and left an envelope for her along with my business card, but she had already finished her shift for the day. I have a PhD and thought that might impress her. I wrote that I would like to meet her for coffee or lunch as I had many questions about Thailand, and it would also be a good opportunity to practice my mother language. She never replied.
Two weeks later, I went shopping again at the same department store and intended to ask Tip whether she had received my envelope with the message. I also wanted to thank her again for her help as my order had arrived successfully. Another sales girl told me she would call Tip. However, unexpectedly, an unknown girl appeared who could also speak my home language. She mentioned that one of her parents came from my country. She said she would handle the matter for Tip.
I told her that made no sense as Tip had handled my order, not her, and she would not know why I wanted to speak to Tip. She said Tip was dealing with another customer and was unavailable. But I felt there was some untruth in what she was saying. I had the impression that everything was arranged so that I could not speak to Tip again. I said, “No problem,” and told her I would wait until Tip finished with the other person.
Finally, Tip appeared with an angry expression and was accompanied by the two other girls. There were three of them, and they told me they would listen to my issue. I felt like I was being questioned by a group of police officers.
The Department Store Encounter
I explained that the other two would not be able to answer my question, which was whether Tip had received my message two weeks earlier. My second reason for meeting her was to tell her that the online order had gone through successfully thanks to her help, as I cannot speak or read Thai, and that I wanted to thank her personally. They replied, “Oh yes, we do know because we know about the message.” They also told me this was not the place to leave a message like that.
I interrupted them and said they did not need to worry because I would be flying back to my home country that night anyway. I then left. They began performing their thank yous, which in my opinion were completely inappropriate after such an unfriendly encounter. I was left wondering which taboo I might have broken in their view. I was simply happy to have met someone who spoke my language in a foreign country and when I could ask a few questions about her country.
