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Ladyboy dating: dos and dont's

dating advice relationships

Whether you've been around ladyboys for some time, or are a total noob to meeting them, if you’ve met a ladyboy online and are planning a ‘real’ date there are certain things you will want to bear in mind before your date begins.
Here are a few Dos and DON’Ts to dating a ladyboy:

DON’T.. Assume that you are God’s gift to ladyboys..

It’s crazy, but some guys do go into dates with ladyboys taking the attitude that ladyboys should be grateful or feel lucky to meet them. These guys are naively under the impression that there are so few guys that like ladyboy it automatically makes them every ladyboy’s wet dream.

Here’s a news flash for you: ladyboys, just like everyone else you’ll meet in life, are individuals with individual tastes. Some love young guys, some fall for the guy who makes them laugh, some prefer blondes, or sweet guys, or even mature guys, their preferences and taste are as varied as anyone’s. What the universally don’t seem to like is they guy who thinks he’s God’s gift to the third sex.

Be confident by all means, but don’t be arrogant or rude.

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DO ..Treat ladyboys with respect..

A little respect goes a long way in just about every society of the world, no more so than in Thailand and among its ladyboy population. It’s not only important to respect someone’s race, culture and religion, but when dating a ladyboy it’s just as important to respect their gender choices.

First dates should always be kept pretty light and simple, so asking a ladyboy about her transition or sexual experiences is not the best conversation starter. Treat her like a lady. Be sensitive. Keep things positive and pay her compliments. If you’re wondering at what age she started taking hormones, or how ‘active’ she is in the bedroom, try holding those questions back for now.

Get to know the person and the personality, not the gender or sexuality. There will be plenty of time to tackle the more serious issues if/when the dating starts to get more serious.

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DON’T..Assume every ladyboy is easy..

Yes, most ladyboys tend to be more promiscuous and sexually active/adventurous than most women, but by no means is every ladyboy looking for sex or easy to get into bed. No matter the background or sexual experience of your ladyboy date, assuming you’re going to get laid at the end may lead to disappointment.

Some ladyboys will be looking for a serious relationship, tired of going on dates with guys who just want sex. So, if you’re just looking to get laid then it pays to be honest before the date even begins, I mean why waste anyone’s time, there are plenty out there who will meet you for no strong sex.

By all means flirt and be sensual, but try not to be offensive or come on too strong.

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DO..Be honest about what you want..

As said above. If you want sex, be open from the start, many ladyboys on dating sites are looking for sex meets (whether that be for money or just fun), if you’re looking for a serious relationship let them know you’re open to that option. Or if you’re just looking to meet and see how things go without making any commitment then tell them just that.

Don’t be afraid of their reaction to your honest, it will be far more uncomfortable realizing you both want completely different things after meeting. Telling a ladyboy you are looking for a long term relationship just to get her into bed may well back fire, when you want to ask her to leave after sex but she’s already tucked up in bed with her toothbrush sitting in your bathroom.

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DON’T.. Believe everything a ladyboy tells you..

Some ladyboys will lie. That picture on their profile may be a few years old. When they said they had only been in Pattaya for 2 months they weren’t including the 3 years they spent in Pattaya prior to those 3 months. When they said they are single they meant single when in Pattaya; their boyfriend in Germany doesn’t count, even though he is sending her money every month.

Go into the date with no expectations and an open mind, and take time to learn the truth.

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DON’T .. Believe everything you tell a ladyboy..

Ok so you lied about your age by a few years, and when you said you had only been with 2 other ladyboys, you only meant this month. That’s no big deal, but try not to let the lies get out of hand, and whatever you do, just because you are feeling in awe or horny, don’t start making promises you probably won’t keep.

Relax. Try to listen more than talk. Just enjoy the date and have fun.

Please do share your tips for dating ladyboys!

Written by: Moo Yung

For the dating ladyboys in Thailand we recommend joining Thai Friendly which has hundreds of Thai ladyboys listed.

For dating ladyboys globally we recommend joining My Ladyboy Date which has attractive ladyboys in many Asian and Western countries.