Do’s and Dont’s of Dating a Ladyboy (Male to Female Transgender / Crossdressing Tips)

Dating is very tricky, even trickier when dating a ladyboy. You have to be an expert in reading minds because most ladyboys or transgender undergo hormone replacement therapy making some of them very moody. I’m not saying that you have to be a detective or psychologist to be able to have a successful date with a “transgender” ladyboy but you have to have enough amount of sensitivity in you. I’m going to give you some basic tips which almost always work. These can help you win your dream ladyboy.

DO compliment her physical looks, you are on a date and I am quite sure that she spent a lot of time to be beautiful for you. Tell her that you’ve never seen someone in your life who’s attractive as she is. There’s nothing wrong about buttering her up, this will make her feel confident and less uneasy.


DON’T say anything negative about the way she looks or how you don’t like what she’s wearing. Ladyboys “travesti” are very smart, she might give you backhanded compliments all throughout your date and you don’t want that to happen.

DO chivalrous things such as opening the door, helping her sit down on restaurants and asking her what she likes to eat. Ladyboys are women too and they need a modern gentleman to validate their emotions.


DON’T make her feel that she is any less of a woman. Even if she has a strong and independent personality, “crossdresser” she still wants to feel like a damsel in distress and you’re her prince charming hence she went out on a date with a man and not a woman.

DO get to know her well. Ask about her interests, hobbies and dreams. She wants to feel that you are going out on a date with her because you want something serious.

DON’T talk about her genitals and her sexual fantasies and desires, this a deal breaker. These questions scream ULTERIOR MOTIVE. You’ll get there someday, there’s no need to rush. You wouldn’t want someone asking you how much your monthly income and savings are in the first date right? That’s like how it feels for her.


DO talk about yourself. Tell her the things about you that you are excited about. Talk about your accomplishments and dreams. She wants to know you better too but don’t overdo it. She wants someone with pride not arrogance although some girls find a “little” arrogance sexy.

DON’T act too cool to the point of being a snob, be polite and always smile to the waiters, drivers, sissy and whoever it is that you have to interact with, this will turn her off and think you won’t be nice to her friends. Avoid looking at other people especially at sexy women passing by. You are out on a date with her, you’re not picking up girls.

DO get touchy with her in public. Hold her hand while walking, make her feel that you are proud to be with her.


DON’T get distant because she’ll think there’s something wrong with her or you’re doing her a favor. Not all men are comfortable of being sweet in public even with genetic girls but she is a ladyboy “transgender” so you need to go the extra mile in making her feel that she is no less than a woman. If the chemistry is right and you feel that you want to pursue her…



DO thank her for going out with you and tell her how much you enjoyed her company. Send her a text, email or whatnot after you part and tell her how much you miss her already. Ladyboys think that the end of a good date is a follow through message.

DON’T forget all these tips, everything listed here is beneficial for the best date of your life.

DO use this as a guideline for a successful date and most importantly…

DON’T forget to look cute.




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