I have read quite a few articles on websites such as Stickman, and various blog posts, about how Thai culture will be highly difficult for Westerners to understand and adapt to. They stress the frustratingly huge culture gap that would cause problems in relationships with Thai woman. However, personally I found that it hasn't been such a big deal for me, and that there really wasn't too much of a cultural understanding gap between me and the Thais.
There are some books I've read like "Thailand Fever" which try to explain Western and Thai cultural differences to both sides. (See http://thailandfever.com/ , particularly http://thailandfever.com/inside_en/all.html ) Personally I haven't found that book to be too helpful. It's more like a review of why my parents behaved the way they did and why Anglos behaved the way they did. Plus the book gives justifications of certain behaviors and attitudes that would not considered to be entirely acceptable by all Thais, especially upper-middle class Thais and Thais with proper krengjai (shame).
Thai and Chinese cultures vs. Filipino and American
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