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Discretion With Dating Ladyboys. Why and Why Not?

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A lot of relationships are out in the open but relationships are not replicated, each one is different. Some relationships have the “perfect” setting but don’t work and some are seemingly unusual but work “perfectly”.

How does a relationship work for a couple without having to sacrifice anything? Is that even possible? These questions get piled up and just go into a blur that we can’t even figure out but here at MyLadyboyDate, we will try our best to give you all the information that can help you in your relationship with your Ladyboy girlfriend.

Discretion is a very grey area in a relationship; we may find it insulting but on the other hand, helpful as well. Why do you need it? Why don’t you need it? What is its relevance? How will it affect your relationship?

Why do I have to be silent with my relationship?

As awful as it sounds, it really is practiced by many couples. Because our society is not yet fully accepting of our choices, we are forced to conceal them even if it’s contradictory with what we truly believe in. Work, family, friends and such factors are what drive you to be discreet about your lover’s identity.


You are afraid that if your colleagues find out about your “sexual preference”, it might affect your status at work and possibly make you uncomfortable with having a healthy working attitude. As much as we would like to see our world as a playground of happiness, acceptance, and individuality, there will still be antagonists that will use your ladyboy relationship against you and take it as an advantage to ruin your “image”.

Working for a huge company is like being a candidate running for politics, if you have a bad image and campaign, you will not win. There is nothing wrong about having a relationship with a transsexual woman but not everyone is accepting of it and there are just envious, greedy and manipulative jerks who are happy to slander it with negative notions.


Family is also a huge factor in your fears of showing the real you. Being a straight man telling everyone you like ladyboys is harder than being a gay man trying to come out of the closet. The media made gay and lesbian cool and mainstream but they left out transgenders in a dodgy, freaky and dark area. You can’t really blame your family especially your parents who were born before the 80’s, most of them still live in the transgender taboo era.


Friends are the people you can count on and share all your secrets with. However, you’re afraid of losing these people because of your choice. This gets harder when you have a friend who is either very religious with strong disapproval of gay people and transgenders or simply a judgmental hater.

Your ladyboy girlfriend is ok with this setting so she says but how does she really feel? You asked her and she said she doesn’t mind but do you really know what’s going on inside her brain?

Why not let everyone know?

Some men are quite brave and they are usually the type of men that are worth keeping. Personally, I don’t really believe that discretion can help your relationship with your Ladyboy girlfriend. It helps with your other relationships but not with her.

Hiding her from the people who matter to you is totally opposite of how you say you accept her for who she is. Caring about the negative thoughts from other people against your girlfriend just goes to show that you think the same and you are one of them.

How would you feel?

Denying a person from your life because she is transgendered is demeaning and worse than denying a mistress. How would you feel if your ladyboy girlfriend denies her relationship with you because of who you are? Let’s say her family is rich and you are poor, she doesn’t tell her family about you because they might disapprove and think of you lowly, doesn’t that hurt? Doesn’t it hurt when someone says he/she loves you but you are being buried deep into the ground like you’re a pungent truth and it is fine if you rot there?

When she says she’s okay

When your partner says she’s ok with being a secret you should think again. Maybe she loves you too much that she is sacrificing by swallowing her pride because of you or she doesn’t want to be a burden to you even if it downgrades her self-worth. You are not the only one who matters in the relationship; your girlfriend is a person like you who has dignity and emotions. She is not a “fantasy-fulfiller” nor a supporting character in your life.

I’ve given you some answers to most of the questions that have been bothering you but I am leaving you with one question that you yourself could only answer.

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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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7 thoughts on “Discretion With Dating Ladyboys. Why and Why Not?

  1. It’s not that ladyboy are just “fantasy-fulfiller”. It’s just that in some society, you have to be very discreet about your relationship, especially religious, homophobic society. You can get your girlfriend and yourself killed just because you decided to be open about your relationship.

    So, your advice in this blog are limited to a small number of scenarios, whereas there’s numerous of them out there, which are way beyond our control. Not everybody has the same life as you are, so don’t judge people who just want to be discreet about their relationship. It could mean their life to them.

  2. I can appreciate the scenarios you listed in this blog, but I need clarification. I would not want to hide (or keep secret) my relationship in and of itself. But, living in the society I live in, would it be so wrong or demeaning to hide the fact that my girlfriend is a ladyboy? She would be a partner in every aspect of the word, but the part about being transgender would be our secret. From your perspective and position of experience, would that be an acceptable scenario? Or would it be construed as not being wholly accepted and/or acknowledged?

    I hope I can get some answers from those of you who may be in or been in a situation like I just described. Thanks.

    1. I believe it’s even the most acceptable scenario. It’s not because you’re proud of having a transgender girlfriend that you should expose her literally to anybody. Like when you introduce your girlfriend to somebody, are you going to say “This is my girlfriend, she is a transgender”? No, you will just say “This is my girlfriend”, period.

      I treat my girlfriend like the woman she is, and I present our relationship to the world as a regular couple (and we are a regular couple!). Her condition as a transgender is only our private matter (mostly, it’s HER private matter). For my family and close friends of course, the information is disclosed, but it was only after we made the decision together with my girlfriend.

      Don’t worry mate, you’re in the right direction. Many transwomen would like to be with an open and respectful man like you.

  3. relate much. it is not easy for us (ladyboys) to have this kind of relationship. there are moments that i got offended, but i still have to do it because i love him. is it love? im so damn! what should i do? do i have to continue this? or stop and look for someone else who is very willing to introduce me to the world?

  4. You failed to answer the last question; why not let everyone know my girlfriend is transgender? Well, why not? One reason I can think of is the man is comfortable with openly dating a transsexual but the girl is still not ready to come out.

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