MONEY will rear its ugly head. Ladyboys never seem to have any money. In fact most of the Thai ladies I also dated seemed to be in a permanent state of not having more than 200 baht to their name.
In my six months living in Bangkok, there was many a time when I couldn't set up a date because the lady/ladyboy in question didn't have enough money to jump on a bus and come meet me in the nearest shopping mall.
So if you want a ladyboy girlfriend, you'll spend a lot of time paying for two. While it's OK being a walking ATM machine if you're getting something in return, if you're not, then it's probably best to move on.
Incidentally, being a geek I've done the math...
If you just want sex with a ladyboy, then go to a bar and find a freelancer. It'll work out 2-3 times cheaper than dating a ladyboy and trying to move the relationship from the first date to some bedroom action.
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