Skip to content

What Ladyboys Find Endearing

Amanda Valentine Dela Cruz

A lot of men on ladyboy dating sites think they’re slick. They think they know it all when it comes to the matters of the heart because they’ve successfully wooed plenty of women before.

But what they don’t know is that when it comes to truly capturing a ladyboy’s heart, they have to play by the rules. If you want ladyboys to find you endearing, and possibly end up with someone who you’re really attracted to, keep reading.


Ladyboys who are seriously looking for a lifetime partner want to be with someone who’s not problematic. She’s going to be living with this person for a long time. She doesn’t want to be with someone who’s not friendly to her circles.


If you don’t have a friendly attitude, she’s going to think that in the future, being with you could ruffle the feathers of the people close to her. You need to be someone who can easily adapt to people from all walks of life.

Trust and believe that just by having a friendly vibe, you’re going to attract more ladyboys. However, don’t mistake friendliness with being flirtatious.


Many ladyboys have been discriminated against. This is why they don’t want to be reminded of it by speaking with someone who doesn’t have ample social graces. Many of them are often overlooked and not treated how they deserve to be treated.

Being courteous will get you many places in ladyboy dating. Practice saying:

  • Please
  • Sorry
  • Thank You
  • Kindly and more

However, overdoing this could also make her feel uneasy. Just do this naturally. Make her think that you’re the perfect gentleman who’s not going to treat her like a doormat.

Moreover, don’t only show courtesy to her. Be mindful of how you speak to other people as well. Avoid nagging about other people. Bad mouthing people she hasn’t met will make her think that you’re combative and disrespectful.


Nowadays, men are less gentlemanly. Because people, in general, allude to the fact that it’s okay to disrespect women for the sake of equality, a lot of men are turning into jerks.


Don’t be one of them. No matter what society tells you, always treat a woman as gentlemanly as you can. You’re not going to lose anything by practicing chivalry. Things like:

  • Opening the car door
  • Pulling out the seat for her
  • Paying the dinner bill and more.

Still works for many ladyboys. Now, if she insists that you don’t do these things, that’s when you stop. But remember, it’s better for her to be annoyed by your chivalrous behavior than risk meeting someone who will think that you’re a jackass and lose your chance.

The first decent dating site for ladyboys & cool guys
Join over 125,000 members
Sign up now


If everyone’s not open-minded, nobody would date ladyboys. This is why you must explicitly represent yourself as someone who’s easy to talk to. Being open-minded will open the key to her trust vault. She will feel that she can share whatever’s in her mind without you, judging her.

Ladyboys who are looking for a serious partner want someone who’s understanding. There’s nothing worse than being stuck with someone who will constantly judge you.

If you don’t want to feel the same way, you must start with yourself. Let her know in the beginning stages of your conversation that you’re open to any type of topic. Make her want to open up to you. She will not only find you endearing, she will also respect you.


Many ladyboys, just like many cisgender women, are in tune with their emotions. Because a lot of ladyboys have gone through many challenging events, they prefer to be with someone with who they can connect intellectually and emotionally.


If you just talk about stuff on the surface like looks, physical intimacy, money, etc., she will think that you’re aloof, worse, cold. Nobody wants to be in a relationship with someone whose heart seems like it’s pumping in a cage.

Added to that, if you’re planning to be in a trans-oriented relationship, expect that there will be people who will be judging you in the future. If you can’t talk about serious stuff with her right now, what will happen if the time comes that you have to face the caveats?


As mentioned, many trans-oriented couples face challenges. This is why ladyboys find men who are optimistic more endearing. If you don’t have this air about you, she’s going to be afraid to take the next level with you.

Why would she invest her feelings in someone who doesn’t seem to be sure of what he’s getting himself into? If you make her feel positive, she will be compelled to get to know you more. She will think that being with you is her possible happily-ever-after.


Of course, because many ladyboys experienced rejection most especially before transitioning, they want to be with someone who will make them feel like they are worthy of romance.


Being romantic doesn’t only end in the physical aspects of a relationship. It encompasses many areas of how a man should treat a woman he desires. This means that you have to woo or court her. You have to make her feel like you’re working for her approval to let you come into her life.

Flowers, chocolates, sweet nothings, all of these are great ideas. Date her regularly or communicate with her consistently if you’re far from each other.


Noone is more annoying than someone who keeps breaking their promises. Don’t be like this. If you want to be endearing, you must be a man of your word. Never promise her anything that you’re not able to do.

There’s a good reason why the saying “actions speak louder than words” is so popular. If you said that you’re gonna call her at a specific time, do it. If you requested for her to communicate regularly, don’t let her be the only one doing her part.

If you promised her that you will meet her, save up for it until you can have her in your arms. Remember, if you’re unsure of something, it’s better not to say anything at all.

Still single and don’t know where to look for Beautiful Ladyboys who are Looking for Love? Why not sign-up on My Ladyboy Date today and see who cupid has in store for you?!

Posted in Love & relationships
The first decent dating site for ladyboys & cool guys
Join over 125,000 members
Sign up now

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.

Related posts

Comments (0)

Leave a Reply

Your email address will not be published. Required fields are marked *