This article is primarily aimed at guys looking to date Thai ladyboys in Thailand. Most importantly, this isn’t an article about getting free sex from dating sites or how to date as many ladyboys as possible without getting caught, it’s an article which should be most useful to those looking to go on a real date with a real ladyboy.
Do Be Respectful
It doesn’t matter whether the ladyboy you are about to date is from a farm in Issan, an ex-gogo dancer, or the offspring of a top Bangkok police chief, if you don’t show your ladyboy date respect – you probably won’t get any in return and things are sure to turn sour.
In some ways Thai culture is very simple; smile at people in the street and they will smile back twice as big, be respectful and get lots of respect in return. However, being respectful doesn’t mean simply holding the door open for your date or complimenting her on her dress choice (though these are good moves!), more importantly – you need to be respectful of her culture and beliefs.
Thai ladyboys, just like the vast majority of Thais, feel very strongly about their family, the King (monarchy), and their religion.
You shouldn’t say anything negative on these subjects (especially when on a first date!). In fact, you are best to avoid any conversation on the monarchy and religion altogether.
Don’t Make Assumption
The ladyboy population are an extremely diverse group of people and to make assumptions about how a ladyboy has grown up, what her ambitions are, what she does for a living, or what she wants simply based on the fact she is a ladyboy – is a pretty foolish move.
Perhaps the biggest assumption that a lot of guys make when dating ladyboys is that their date is really after money or a boyfriend who will take care of them financially. In some cases this is true, but you should never go into a date assuming this or it might lead to a very awkward and uncomfortable situation.
I’ve met ladyboys who are architects, accountants, cartoonists, phone technicians, and history students – all of which had very individual and unique tastes and hobbies. Don’t just assume that all ladyboys on dating sites are looking for sex and / or money. If you are really unsure what the situation is or what they want, simply ask, but be sure to do so in a respectable and friendly way.
Do Be Honest
Just as you might want to ask a ladyboy of her intentions or what she is looking for, you should be honest about your own intentions.
If you are using dating sites looking for free sex, then it’s best to be honest about it from the beginning. There are plenty of ladyboys out there on dating sites looking for sex and friends with benefits, but there are also a lot of genuine ladyboys looking for boyfriends and serious relationship. If you make out you are looking for a real date knowing full well you just want to get laid, in the end you’re just wasting everyone’s time.
If you just want to get laid stick to the bars, or seek out the ladyboys online looking for the same thing. Like I said, there are plenty of them around. Trying to bed a ladyboy who you know is looking for a relationship is going to be a lot of time and trouble and you’ll either end up looking like an asshole and upsetting them…or you may even get into a bit of trouble (no one wants to play the game Angry Ladyboys).
Don’t Be Too Honest
While it pays to be honest about your intentions, just as with any first date, it doesn’t pay to be too honest about everything.
Yes, in general ladyboys tend to be more promiscuous than girls, and often have had more adventurous backgrounds and sexual experiences, but that doesn’t mean you need to tell them about how many ladyboys you’ve already bedded and that time you had a 4 some in the hotel pool.
Any first date should be kept simple, fun, and free of heavy conversation. A date with a ladyboy is no exception, and talking about sex and ex-partners is never the way to get off to a winning start.
Do Make an Effort
If you’re going to take a Thai ladyboy out on a date, treat it like you would any date and make an effort. Expensive restaurants in Thailand are not actually that expensive, you can eat in some of the best restaurants in Bangkok for under 1000 baht per person, so why not take her somewhere special.
If you do take her out to a nice restaurant, bar, or club, dress the part. If there’s one stereotype that’s true about ladyboys it’s that they love to dress up and look good. If you do end up in a relationship with a ladyboy you’re going to curse the amount of hours she spends doing her hair and make-up or shopping for shoes and clothes…but when it comes to date time they’ll be turning all the heads in a positive way.
Don’t Pressure Her For Sex
Similar to what I’ve said already, don’t assume that every ladyboy you date is a hooker or looking for sex. Even if your date tells you she once worked in a Bangkok beer bar, don’t assume she’s an easy lay.
Be respectful, if sex happens then it happens but don’t go into the date assuming it’s a given just because she’s a ladyboy. By all means flirt and be sensual, but don’t be too forward or come off as a sex offender – as said earlier, if it’s sex you’re looking for it would have be easier to be honest from the start.
Do Be Proud
If you’re feeling ashamed to be seen with a ladyboy or worried about what other people might think, then maybe you’re not ready for your first ladyboy date.
You’ve got to leave all that baggage behind you if you’re going to go on a date with a ladyboy, especially in Thailand. It’s not like everyone is going to stare at you and call you a freak, if anything the people starring will be wondering how the hell a guy like you landed such a hot date. If you go into it with any sense of shame or social shyness you’re only going to make your date feel totally embarrassed and uncomfortable, which isn’t cool.
Be proud about the hot date on your arm. Don’t walk 5 steps in front of her or take her somewhere quiet and away from others. Let her see that you’re comfortable with who you are and you’re not ashamed to be seen with her.
Do Enjoy It
Regardless of all the tips and rules and things you read in guides and blog on dating, the most important thing when dating a ladyboy is to enjoy it. I find ladyboys to be among the most fun, kind and funny people I’ve met, so full of surprises and usually a total pleasure to be with. Don’t over think it, just be polite, be yourself, and have a great time.