How to date a ladyboy

Cliché as it may sound, no people are alike, especially for ladyboys since they come from different backgrounds and have different experiences leading to who they are today. As such, there is no single way to please a transgender date but several years of experience dating transwomen taught me a thing or two, especially the things that should be avoided. Here are some tips to help you in dating ladyboys that can make a difference in your relationship.

Since transgender women identify and live as women, the rule of thumb to treat them as such. Dating transgender women should not be any different from dating a biological woman. They long to be accepted for who they are and as their date, treating them as women is the way to go. Asking her what her favorite food is can leave a good impression. In my experience, knowing several phrases from the language of my foreign transgender date makes her very delighted.

Couple holding hands at the restaurant

Refrain from asking questions that are too personal unless they communicated to you that it is okay with them. Questions relating to their virginity, sexual preference, and sex life should be avoided because these topics are generally not appropriate especially on the first few dates. Asking if they had sex with a girl or if they have a vagina is a deal breaker. Their status whether they are pre-op, post-op, or no-op ladyboys is none of your business because the decision to undergo any procedure is their personal choice. They would share their experience eventually if they are comfortable enough.

Ask her about her hobbies and the things that make her happy. Let her pour out information about herself without pressuring her or making her uncomfortable. Showing interest regarding her future goals and plans is also a way to keep the conversation going.

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While transgender women love to hear compliments, avoid those that may come off as insults. Do not say things like, “you really look like a woman” or “I have no idea you were trans because you are so pretty” because these statements imply that they are not women, which they are.

Listen with an open mind because she has a story to tell. If you are dating a transgender woman for the first time, don’t blurt out things like “I only dated women before” because as I said, they are women too. Instead, say that you don’t have experience with transgender women.

Research and try to learn about transgender women in general—what they are and what made them who they are. Don’t come off as unknowledgeable or insensitive especially by asking what their previous name was. Also, avoid terms such as tranny and shemale because these terms are offensive. Treat them with respect as you would do with cisgender women.

I may be guilty of this during the early stages of dating transwomen but hiding them would not produce any positive result and would have a negative effect on your date’s feelings. Instead, take them out and when they are ready and involve them in your social circles. They are amazing women so don’t be afraid to show them off.

Some ladyboys undergo transition and dating one that is currently on that phase may have emotional issues that you will have to deal with in an understanding manner. It would show that you are a gentleman and they will greatly appreciate that.

Follow these tips and don’t waste the chance to have a deeper and meaningful relationship with the wonderful woman you are currently dating or the woman you dream of dating.