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Dating a Younger Ladyboy. Is it Possible?

Amanda Valentine Dela Cruz

Here at My Ladyboy Date, we’ve already shared tips from the angle of a ladyboy dating an older man. But because of a comment that we’ve received from one of our readers, Joe, recently, asking “I’m very insecure, but just so in love. My question to you is: How much does age mean? I am now 55, train a lot, am hygienic and proper, she is 36. is there any chance in your opinion. Pls be honest”, we’ve decided to create this guide.

If you’re dating or eyeing a younger ladyboy and you have doubts about whether it’ll work or not. And if you can achieve real love even if she’s 10 or more years younger, keep reading!

Advantages

But of course, let’s not discount the fact that dating a much younger partner has its advantages. They say that when it comes to true love, the benefits and advantages don’t matter. But realistically, a relationship is based upon the foundation of giving and taking.

Confident young woman in a stylish gray dress poses with one hand on her head, adjusting her glasses with a bold expression.
Confidence is the best accessory. – pexels.com

And it’s time to appreciate what you can get from the taking spectrum.

More Adventures

They say that when it comes to wisdom, one must factor in one’s age. People tend to reinforce that wisdom comes with age. But it doesn’t mean that someone younger can’t teach you a thing or two. Even if you think these lessons are trivial, you must be aware that some of the simplest things in life are the ones worth looking into.

In this case, a much younger person is more likely still seeking many adventures. And along with these comes happiness. There is no age limit when it comes to having fun and a happy disposition provides a healthy life.

Lots of bedroom moments

They say that men tend to maintain their appetite well over years after their senior birthday. Because of this, single and middle-aged gentlemen tend to select a much younger partner who still has their virility intact.

Compatibility in the bedroom is very important and whoever says it isn’t probably still participates in Disney Princess movie marathons. You see, making love is the highest form of expressing one’s emotions. And without it or the lack of it, the other may feel rejected.

You’ll be the envy of your male friends

Outings with friends and couples, reunions, black tie benefits, downtown dates, etc., whatever it is, having someone young and beautiful beside you provides an instant boost of confidence.

Not to objectify ladyboys and women in general, but this is the reality. Women love to flex their jewelry and handbags while men love parading their cars and babes.

She can take care of you when you become really old

One of the biggest fears of people aging is probably the day when they get sent into a nursing home. If you marry someone particularly younger, most especially a ladyboy who most likely comes from a very family-oriented background, a home for the aged will be the least of your worries.

It is not a requirement for someone old to be sent to this type of facility if they can take care of themselves or… if someone from home can take care of them. Would you rather spend your remaining days in a place whereby people are paid to take care of you (not that there’s anything wrong with professional help), or spend them at your home with someone who loves you and truly cares for you?

It may be true love

Apart from the most obvious benefits, who knows? Maybe she’s truly in love with you and she didn’t choose to be with you just to have a better life. When it comes to true love, age is just a number.

Don’t let the judgment of others cloud your reality. Love can exist anywhere. It can grow even if it’s surrounded by prejudice and bigotry.

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Disadvantages

But of course, it’s not all rainbows and butterflies. There are many disadvantages if you don’t always view life from rose-colored glasses. 

A relaxed person sitting on a leather couch in moody dim lighting, holding a glass of red wine while engaged in a phone conversation.
Late-night thoughts and deep conversations. – pexels.com

Below are the reasons why the likes of Joe have apprehensions in believing that a relationship between an older gentleman and a much younger ladyboy won’t work.

She might be a golddigger

The reality is, most especially if a ladyboy is in her early 20s or early 30s, obsessed with her looks, and material things is that if she’s dating an older guy, she’s probably just dating him for his bread.

There’s nothing wrong with trying to live a certain lifestyle but only if it’s not on the expense of others. A person who has not worked hard for a certain period of time and who only obtained the things they show off are probably the ones who only hop from one relationship to another just because of the money.

This is one of the easiest to determine whether true or not so be honest with yourself, is she a golddigger?

Other people will think she’s only after your money even if she isn’t

To answer the question of Joe specifically, if she’s 36 years old and he’s over 50, there’s a huge chance that she’s not just using him for money. From the way he wrote his question, he seems like he’s the one feeling like he holds the shorter end of the stick.

So now, the problem is, from an outsider who will experience the first time seeing these numbers, the thought could be that she’s only using the man for his money. Even if it’s not true, it can be hurtful especially if the judgments are coming from the people close to the guy.

Now, if you’re the type who’s quite secure about what you have and the opinions of others don’t matter, keep dating your younger partner!

Hard to keep up with her strength

Not to say that all middle-aged men require a cane to walk but to compare the energy levels of a particularly young ladyboy and an older man is like watching a crustacean compete with a shark in a race. The disadvantage is too obvious.

This strength can be seen in terms of traveling, making love, socializing, and more. The parity can widen more but if you’re up for the challenge, why the hell not?

If you’re insecure, you might think she’s going to cheat on a younger man

Not to be cynical but if you lack the confidence that one must possess to make a relationship like this work, it’ll never work. You’ll always feel conflicted and unsafe if you’re not able to erase all of the doubts in your head.

This is not healthy for you and your partner and it’s best to end it before it begins. You can’t go through life tightening your grasp whenever you’re out and she sees a man who stands above 6ft 2in with big guns. You can’t let every beach Adonis in your summer vacations cloud your special moments.

You have to take care of her financially (Doesn’t apply to everyone but a norm)

Most ladyboys who grew up in Asia will be financially dependent on you after you decide to be together. If you can’t step into the role of a provider, dating a much younger ladyboy will not work.

You see, normally, it’ll be the guy, taking the ladyboy into his home country for better opportunities and the legality of marriage. And along with this taking are her current career, means of living, family and friends to count on, etc.

She will be divested and you’re responsible for how she’ll be able to start a new life in your place. This kind of relationship requires maturity from the man. Not because you’ll spend on her means that she just chose to be with you to suck the blood out of you. You should be aware of her sacrifices as well.

Is it possible?

To answer Joe’s question about whether there’s a chance for a much older man and a much younger ladyboy to have a successful relationship, with all honesty, YES!

A romantic moment captured at sunset, showing a barefoot person on tiptoes reaching up to kiss their partner near a lake.
Love rises with the sunset. – pexels.com

But like any other relationship, it requires:

  • faith
  • open-mindedness
  • clear communication
  • endurance
  • maturity
  • and lastly, ample time to get to know each other better

Now, if you’re still single and have dreams of spending the rest of your life with your ladyboy soulmate, your first step must be to create a My Ladyboy Date account. It’s the first decent dating website created for ladyboys and the men who love them.

True love waits but you’re not getting any younger! Sign-up today and start your new love journey!

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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