Build your relationship slowly. Women or a woman are poor reasons to move. If you're contemplating retirement and Thailand sounds like it's for you, take a few short trips, travel around the country, and formulate a plan. Thailand might be the place to call home but take your time.
2) Take a couple of trips here before committing. Travel around the country, see the sites, and get a feel for the people and the culture. If after several vacations you feel like you want to move here, commit for a longer period, perhaps six months to a year.
My original plan was to stay for one year, and if things didn't work out, I would have a little stashed and to start my life again in the United States.
3) Take 6-12 months of living here as a trial period. Learn to speak Thai — at least the basics. This help you communicate with others and help you understand what people around you are saying, good, bad, or otherwise. You can always play dumb, "I'm sorry, I don't speak Thai," and determine what sort of people you're involved with.
4) While on your vacation, scout for places to live. Ask around, ask friends, ask Thais. Sometimes the internet can be a good source of info but if an apartment is shown in English, chances are you are paying a premium for being a Farang. If you choose to come for six months to a year, you will have a good head start and should already have a place in mind to stay. Bear in mind, you may be required to sign a six or twelve month lease by many apartments.
5) Thailand is more expensive than you think. If you want to eat at food stalls, buy inferior products, and live in a studio apartment, sure, you can live for less. The other day I went and looked at Casio watches again. I decided to look at them because in my video, Can You Live in Thailand on a $500 a Month Budget, some questioned whether a Casio is expensive. An expensive watch is a Piaget or a Rolex. A Casio is cheap. But if your budget is only $500 a month and the watch costs $250, it's expensive. There were several styles but the prices ranged from around 3000 baht all the way up to 9000 baht, or around $300.
Go out for Sushi at a decent Japanese restaurant, it'll set you back $30-$40 for two people. When my wife and I go out with our kids to our favorite Vietnamese restaurant, we spend 1000-1200 baht. That's $33-$40. Definitely not expensive but the point is, Thailand is nowhere as cheap as some may believe. You can get just about anything here but for those less-available items, you're going to pay.
Like I always say, Thailand is cheaper in many ways, but it's not cheap.
6) Right now, you may think Thailand is the greatest place on earth. Visiting and living here are completely different though. What would never bother you on holiday might drive you mad if you're living here. Being expect to tip on a holiday is probably no big deal. If you live here and a taxi driver expects a big tip simply because you're a foreigner, it can get on your nerves.
7) Be careful what you wish for. It takes a special type of person to live in Thailand for the duration. If you're going to cry about flooding, the heat, how this or that is too expensive, you might not want to live here. Accept what is and stop thinking about how things should be.
My own personal pet peeve is Espresso. If a coffee shop can't make my Espresso properly, it pisses me off to no end. But I get over it. I go somewhere I know can make a proper Espresso and I'm fine. But you need to be able to find solutions to your irritants or you won't make it here.
8) The longer the stay, the harder to go back. If you are 24 years young, you have your whole life ahead of you. If you teach English or work in any other job here for the next 20 years, what are you going to tell a future employer back in your home country? You may or may not have to start at the bottom just to get a job.
9) Your problems, your fears, your flaws, and all of your positive traits are always with you, no matter where you go. They follow you forever. Going abroad may be the answer for some or it may be the beginning of a string of problems. But make no mistake, if you're not in paradise at home, you will never find paradise abroad.
10) Come with more money than you think you'll need and spend less than you think you should. Be prepared to take a year to network and to start earning a living. Expect success but be prepared for failure...