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Ways to Surprise your Ladyboy Date

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If you’re looking for ways to surprise your ladyboy date, or your girlfriend if you’re lucky, please keep reading.

There are many articles about surprising women yet surprisingly, you’ll find close to none when it comes to dating ladyboys.  Please know that I’m a ladyboy myself.  However, I’m not the paragon of ladyboys so still please take this with a grain of salt.  The list will include what some of us ladyboys will be happy to experience. Enjoy!

Do to Yourself

In this section, we’re going to discuss more what you can do to yourself to surprise her as a reaction. Please know that this may or may not be applicable to you so take all of the tips here with a grain of salt.

A New Haircut

Dear gentlemen, the majority of ladyboys LOVE a clean-cut guy. If you want to surprise her in a positive manner, it’s time to tweak and improve your grooming. Not only will it help you in the long run, but it’s also going to guarantee your ladyboy girlfriend’s approval.

Men tend to overlook the importance of grooming because a lot of them feel that most women don’t care about looks. This is not the case. Ladyboys are very particular when it comes to transitioning and a lot of us appreciate and are in tune with aesthetics.

men haircut

You don’t have to look like a Ken doll but a sleek haircut usually suffices. Don’t go overboard as well when it comes to experimenting with your style. Not because a hairstyle is on-trend necessarily means that it’s going to look good on you.

The key to knowing what suits your face best is your face shape. Hairstylists who know what they’re doing will be well aware of your proportions and what will match your face shape. Dear gentlemen, compared to us ladyboys, you don’t have to spend a lot when it comes to grooming so PLEASE don’t skimp when it comes to getting your hair done.

Learn what She Loves

A man who likes to be part of his partner’s life and shows it in obvious ways is a very attractive man. For example, your partner loves to swim, this is when you have to start learning how to so you could join her in this activity. If she likes to paint, it’s time to buy a canvass and start practicing your strokes.

couple in a restaurant

It’s not about being too codependent or having no identity. This gesture will only bring the two of you closer and trust me, it works! My ex-boyfriend had me do a lot of things and watch a lot of shows that I did not have an interest in from the get-go but I’ve learned to love everything he recommended because I’ve enjoyed every moment I’ve participated in those occasions.

Speak Her Language

English is considered as the universal language and it’s quite fundamental in terms of dating ladyboys online. However, learning your ladyboy girlfriend’s language can be very attractive as well. This goes to show that you don’t only fancy her but you’ll actually go all the way in terms of being a part of her life.


Most men who seek ladyboys for relationships online choose girls from overseas; particularly Thailand and the Philippines. You don’t have to sound like you’re a native speaker of their language but knowing some words that revolve around compliments and affection may suffice. Surprise her by telling her how much you love her in her native tongue and see how she reacts.

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Do to Her

This section will solely include the things that you must do to or for her. It’s quite more actionable and reactive because the tips here will directly involve your ladyboy date.

Unannounced Visit

If you know where she lives, show up on her doorstep with a bouquet of flowers!  What would make it even sweeter is when you pretend to be a delivery man with the undressing of the helmet reveal!  If a guy would do this for me, my heart would melt and it’ll be something worth remembering for the rest of my life.

men's gift

The impression you’re going to leave to her is that you are a loving, spontaneous, and one of a kind gentleman.  However, it will not be my fault if she happens to be cheating on you and you find a man living in an apartment with her LOL.

Spicy love

Intimacy with ladyboys is spicy enough. However, if you want to turn up the heat further, you must surprise her with new bed knowledge and methods. Try introducing a little kink to your ladyboy love. Just don’t go overboard because she might think that you’re fetishizing her.

There are a lot of things to do in the world of Bee DSM and it’s not all about pain. There are cosplays, roleplays, submission, and domination activities that both of you can enjoy without having to inflict or receive pain.

couple in a bed

Moreover, spicy intimacy doesn’t only revolve around Bee DSM. You may also change the setting of your bout. A lot of couples find public intimacy to be thrilling. You may try doing this in a park, the lavatory, or anywhere that provides the chances of being caught. The rush from the feeling of getting off while being nervous that someone might see the two of you can be quite adventurous and memorable.

However, if you don’t want to risk public scandal, you may simply try new positions. There are more than a hundred love-making positions and I guarantee that you and your girlfriend haven’t tried even more than five of these. It’s time to invest in a good Kama Sutra handbook and see what’s in store for the both of you.


A lot of you may skip this because you may think that gold diggers are the only ones who love receiving gifts. Most men today are quite wary about their wallets and dating. However, nobody’s telling you to buy her the latest Louis Vuitton purse or Hermes handbag.

gift box

There’s a lot of gifts that you can buy her without breaking the bank. When people say jewelry, we tend to think of hundreds of thousands of dollars. However, you can buy her a nice piece of gold necklace for around $200 or so. Besides, you’re only going to do the gifting occasionally if generosity is not in your nature.

Gifting is the easiest way to surprise somebody. Although not all ladyboys appreciate material things, I guarantee that every girl will appreciate a nice set of earrings.

Gourmet with Love

I personally believe that every girl dreams of being with a man who knows how to cook. When I say who can cook, I don’t mean someone who can boil an egg. If you’re good in the kitchen, you will rack up a lot of points from her. Surprise her with a nice meal that you’ve made from time to time.

cooking men

Make a lovely presentation as well. Nothing feels more heartwarming than a warm meal from the man she loves. I’ve never experienced being with a man who can cook and if you’re single and you’re one, don’t hesitate to write a comment below xo.

Lovely Dinner

The reason why I put emphasis on dinner and not any other meal is because…

Lunch is for friends, Coffee dates are for Tinder dates that you’re unsure of, and Breakfast is for your wife which she isn’t yet.

couple at a restaurant

I know how most of us today can get quite busy but what kind of girl turns down a dinner date from a man he likes.  I’m pretty sure that even if she’s not in the best mood, she will agree to go with you and ENJOY it.

Presentation is key in making lovely dinners.  Don’t just take her out in a random Chinese restaurant and eat wonton.  She deserves more than that.

Lastly, I’m going to share with you a topic that is exclusive to ladyboy dating and what will set this article apart from the rest of dating articles online.

Surprise Event

Most dating websites would deem this to be indiscrete and unnecessary but if you are dating a ladyboy and you want to make her feel comfortable about who she is and that you’re very proud to be with her, invite her on occasions that she knows matter to you.


Let’s say, the birthday of your mother or your high school reunion.  If you are confident enough to invite her into gatherings with people who matter to you, I’m pretty sure that she will feel more than elated and will think that you are not ashamed to be with her.

Nothing’s sweeter for a ladyboy than to feel that her man genuinely loves and accepts her no matter what may go through.  If you are able to do this, she will surely see that the foundation of your relationship with her is not only built-in attraction or anything superficial, but with true love, strength, and inclusivity.

I hope that you enjoyed my tips.



Posted in Love & relationships
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About the author

Amanda Valentine Dela Cruz
Amanda Valentine has been a writer for My Ladyboy Date for over 10 years. She writes various topics on trans dating and other trans-related content. Her personal experiences as a transgender woman have given her a unique point of view on trans topics. She has written 5 books on trans women’s relationships and has made it on Amazon’s best-seller list. Her book “Dating Transgender Women for Gentlemen” reached #3 on the Transgender Studies category on Amazon. Her love for writing started when she won a poetry contest in 4th grade which made her pursue a career in literature.

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