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DO’S and DONT’S of Dating a Ladyboy

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Dating is very tricky, even trickier when dating a ladyboy. You have to be an expert in reading minds because most ladyboys 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 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.

Early Stages

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 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, 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.

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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 on 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 attractive. DON’T act too cool to the point of being a snob, be polite and always smile to the waiters, drivers 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 hot 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 with being sweet in public even with genetic girls but she is a ladyboy so you need to go the extra mile in making her feel that she is no less than a woman.

Follow Up

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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About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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9 thoughts on “DO’S and DONT’S of Dating a Ladyboy

  1. This article is really ignorant and transphobic. I am pretty sure that most transwomen, if not all, including myself, don’t like to be labelled as ”ladyboys”. Why don’t you have a real transwoman write an article for you and at the same time you can change to name of your website. While you are at it maybe you should look into an anti-oppression training and learn about exploitation and tokensation of trans* people.

    1. Thanks for your comment, as it is for me a good opportunity to explain how the choice of the “ladyboy” term is wise (despite some might think).

      First, I’d like to tell you that the writer of this article is a transgender woman from Philippines, her name is Gabrielle Lynne Dela Cruz, you can look her up on Facebook, Google+, LinkedIn, oDesk… she’s a professional writer and has profiles on various professional networks (additionally she’s a friend of mine).

      Second, for the sake of History, I’ll remind that “ladyboy” was originally an English translation for katoey (the Thai term for more or less defining MTF transsexuals, but kind of widely used also for effeminate gay men… there is no exact equivalent in our western cultures — I suppose you’re a western individual, my apologies if you’re not). In Philippines, we have local terms such as “bakla” and “bayot” which also make no distinction between a transsexual woman and an effeminate gay. Then, throughout the years, and because transsexual women are a fetish for a lot of men, “ladyboys” have been associated to activities that are sexual in nature (say “ladyboy”, everybody think “adult entertainment industry in Thailand”, right?) and adult videos (oh google for “ladyboy” and you’ll see the result, although we managed to rank first on a lot of queries, which supports our vision, I’ll explain in the last paragraph).

      We are close to many LGBT (and especially trans) organisations here in Philippines who appreciate our work, how we aim at educating trans-oriented men and the general public. Producing quality and decent content on the word “ladyboy” is slowly helping to make a change in how people see… well… “ladyboys”, and as a consequence, transgenders as whole. At MyLadyboyDate, our staff is made of transgenders, and men who have transgender partners. We participate in LGBT events (although we try not to get involved too much in politics) and we are well aware of the terms, what they mean, how people understand them (or not)…

      We try to reach to people and spread a message. Our message is that “ladyboys” are not what the general audience seems to believe. And we made the bet that we can spread this message in the most efficient way by, well, talking to the people who don’t know the difference between ladyboy and transgender. Because the people who know that difference, well, they don’t need our message. By employing the term “ladyboy”, we succeeded to reach to transgenders who didn’t even know that themselves, we reached to men who were too ashamed of openly being with a transgender partner. We opened some minds…

      And if we shocked (well, if I wanted to lead an anti-racist message for black people, I would definitely use a not politically correct word such as “N*****” because it will reach more people), well I’m sorry if you got offended, there is really a second degree to understand in what we do here. But the thing is, leave appart the term “ladyboy” and I’m sure you’ll love our content, if ever you read more, it’s a love message, it promotes the talents and qualities of transgender people, it shows the good example that love relationships between transgenders and men are okay and shall be accepted.

      We bother less about labels than about the core of our message (we’re not into politics…). And we carry the exact same message that our LGBT organisation fellows do, believe it or not (it’ll just take you to read some of our work to figure it out).

      Again, thank you for pointing this out.

  2. Most of the DOs and DONTs are quite plain….the same could be used for anyone. They are stating the obvious. How about how to fill in the blank in a conversation?Most of the ladyboys I have met are quite borring or have the usual “let’s talk about love, life, the weather and food”. Not bad personnalities…..but borring. Kind, honest yet dull and uninteresting people. This was my experience but hopefelly, I will meet one that will change this!

  3. Gabrielle Lynne Dela Cruz – you are absolutely gorgeous. Oh how I wish I
    had the honor of being able to take you out for a nice quiet romantic
    dinner. You are very very attractive.

  4. “Tell her that you’ve never seen someone in your life who’s attractive as she is.” – I disagree with this – please only tell her this if it’s true… honesty is important too.

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