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Why Do Some Ladyboys Date Older Men?

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Have you ever wondered why many young ladyboys choose to date older men? It might not be as simplistic as a younger individual seeking a relationship with an older, financially secure partner. Maybe there are other reasons that are more valid rather than… just reducing two individuals’ relationship into something of convenience only.

Common Reasons

Today, you’re going to find out the most common reasons as to why some ladyboys only date older men. Please take everything with a grain of salt. This may or may not apply to you.

a curious old man

Physical Attraction

The saying that men age like fine wine doesn’t exist for no reason. There are older men who are quite attractive and this is why some ladyboys fall for their “daddy” charm.

Not everyone’s into the boy-next-door look or the typical hunk. Not everyone who’s into an older man is only in need of financial security. You have to acknowledge the fact that there are ladyboys who are solely attracted to men of a certain age, sometimes, this attraction can go well over 60+!

Gentlemanly Behavior

Older people, along with wisdom, learn proper etiquette. This is why most older men are very gentlemanly. They know what and what not to do when it comes to being in a relationship and treating a ladyboy. They also are more empathetic because they’ve already had bad experiences in their past flames.

Mental Seduction

Many ladyboys enjoy being with older men because their experiences have helped them a lot of knowledge. This can be very stimulating most especially in conversations.

Something worse than getting a ladyboy pissed is getting her bored and if you’re not offering anything in this area, the relationship will go stale and she will be seeking new adventures with someone who’s more exciting. Other than that, some ladyboys are simply sapiosexual.

Not to say that younger men are dumb but they don’t have as much experience in life as their older counterparts who’ve probably seen the world in a merry-go-round motion.

Matured Outlook

A lot of couples bicker about the littlest things and one of the perks of dating older men is they are more patient. They know when to dignify a hissy fit and when to not. They also know not to escalate arguments by giving way and focusing on other more important things.

Financial Security

Not to be redundant but in reality, many ladyboys choose to date older men because of security. But this doesn’t mean that they’re only after the money of the older gentleman.

What this means is that they want a brighter future and prefer to spend their lives with someone who will less likely encounter financial problems. Many ladyboys come from deep poverty and this could be the most reachable option for them.


If a ladyboy’s dating an older man, maybe she’s not really into a guy like this. It just so happened that she found her soulmate in his form. Different people have different standards when it comes to their soulmates. Maybe, she sees beyond the age difference and that she’s genuinely in love with the soul of her partner.

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Emulating Older Men

Not to say that you should not enjoy your youth because after all, it goes by so fast. But if you’re at the stage of your life wherein you feel like a shift must happen for others to take you seriously and for you to have a more “mature” image, keep reading.

an old man


Many older men have nothing to prove anymore and that is why they dress up in a classic and stylish manner. They don’t select flashy clothes anymore and that is why many ladyboys enjoy going out with them. When it comes to STYLE, less is more.

Added to that, this type of nonchalance also adds to their “masculine” appeal which a lot of ladyboys go gaga for.

Improving Manners

Manners are very important when it comes to dating. If you don’t have enough of it, you’re going to repel many people. Not to say that you have to follow everything from Emily Post’s etiquette book, but at the very least, you have to have an idea of what basic manners for gentlemen are.

A simply pulling the chair for her will get you a long way.

Reading and Researching

People naturally idolize people who they deem to be better than them in different aspects. And one of these aspects is intelligence. If you know many interesting things, you’re going to find a topic that will touch her heart and make your conversations more meaningful.

This is why you must always read and research in your spare time. Start this healthy habit by reading the news for at least fifteen minutes a day. You’ll see great improvement in your conversations with people.

Seeing The World in Another Light

A lot of young people are quite dismissive and want to prove to the world that they know better. Don’t be one of them. A real intelligent person is someone who knows to ask more and discover new information with their own efforts.

This way, you will learn how to empathize and not judge someone without trying to get to know where they’re coming from.

Securing YOUR Future

When you have passion, drive, and perseverance, you will reach your goals. You don’t have to be a millionaire in your twenties to attract ladyboys, but if you know you’re working hard in securing your future, they will gravitate towards you because you will have this dependable energy and aura.

You CAN’T Fight Destiny

However, if your type has set her boundaries and told you that she is in love with someone much older and that she won’t be able to love you back, it’s time to move on. Never fight with destiny because you’ll always lose.

Cast a wider net and be smarter with your search. My Ladyboy Date has plenty of decent ladyboys who are just like you, looking for genuine love. Maybe she’s online and maybe you are her destiny!

Sign-up Today and See What Happens Next!

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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