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Transgender Women Dating Tips for Newbies

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Dating transgender women can prove to be daunting. However, it’s not as complicated as detonating a bomb. It’s also not a landmine field either. I’m a transgender woman and a dating coach. Don’t worry, you’re in the right hands.

However, when dating a trans woman, you must know not to just dabble your way into it.

Don’t expect success just because you belong to the league of straight men. Preparation is key because there are a lot of unwritten rules and transgender dating tips that are not easily available on the internet.

Where to Begin

Before we get too in-depth, you have to start with the basics and fundamentals. Knowing this type of information will help you a lot most especially if you’re a newbie in the world of transgender dating.

There are certain things that you must not say and do. Trans people  have been discriminated against and oppressed over the years. A little bit of sensitivity and empathy won’t hurt.

Address Her Properly

Transgender women are women, PERIOD! You have to take this to heart.

If you have reservations when it comes to the womanhood of transgender women, they’re not the right type of woman for you.

Happy transgender women

If you question her existence, it will result in you, using other pronouns apart from:

  • she
  • her
  • hers
  • herself

and others that pertain to women, you’re not going to succeed in successfully finding a proper transgender girlfriend.

Don’t Strip Her off Dignity

The majority of men online only date transgender women to satisfy their curiosity and fetishes.

Please don’t be like them.

They are called tranny chasers and they’re a dime a dozen.

sad trans women

These men are only interested in transgender women for one thing. That thing is what’s between her a transgender woman’s legs. A transgender person is an individual and they’re more than what’s underneath their underpants.

If you want to have a serious relationship with a transgender woman, don’t make her feel like you’re only interested in fulfilling your carnal desires at her expense.

No Stringing Along

Yes, I understand that some of you may be totally new to dating transgender women.

You’re still testing the waters and are unsure if you truly want to pursue a long-term relationship with women like me.

men with 3 trans women

However, if you’ve gained enough experience already and you’ve come to the conclusion that you won’t be able to commit to a serious relationship with a transgender woman, please do not string anyone along.

This is what truly hurts and karma will truly get you back. If you’re only in it for steamy encounters, you must be completely honest from the get-go. Do not use anyone just to fulfill your needs.

Transgender women are human beings with emotions. They do not deserve men like you.

Be Her Ally

Transgender women have gone through enough already.

They don’t need another person to defy and deny their existence.

If you truly love transgender women, you should be by her side on the fight for transgender movements.

couple on a bed

These movements are not only for her welfare. They’re also responsible for making normalcy of possibility to remove the stigma that’s encompassing trans-oriented relationships.

If these movements are supported by enough people, dating transgender women won’t be seen as tabooed and wrong anymore. This will make your life easier as well if you come to think of it.

Added to that, just imagine how your simple allegiance would help a lot of suffering transgender women around the world.

We do not deserve to be treated unequally and be seen as people without dignity and rights. All we want is to live with the same opportunities that cisgender men and women obtain by birthright.

Now that you know the basics, let’s get in action!

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Dating Transgender Women Online Tips for Newbies

Let me preface this by saying that I’m a transgender woman and in no way a dating expert; a coach but NOT an expert. I’ve not slept with the male global population yet.

When I do I’ll let you know.

I have transgender women friends who found love on My Transgender Date. I’m going to share with you the most common things that we peruse when we try to get to know men.

Added to that, some trans girls are trans lesbians, if they’re not into men. Respect their preference.

Profile picture

This is the first thing we see and we need something to grab our attention for us to swipe right.

Some of my transgender friends like a man who’s confident about his body, hence, they swipe right for the guys who take topless selfies.


For me, however, I like a man who’s more nonchalantly out there. I like it when a guy’s not trying too hard and gives me something to be interested about rather than his ripped body.

Photos in:

  • the office
  • sports
  • travel

or a profile photo with:

  • friends
  • pets
  • and family
  • usually hit the spot for me

Images like those tell a story and show that a guy is more than just a pretty face. I want to see that a guy is stable, loves to have fun, capable of caring for people… ok, the list will be too long but you get the idea.

About me / Description

This part is solely from my point of view.

I love it when a guy is eloquent and can express himself intellectually through his profile page.

Something about a quirky guy who keeps it short and cute also magnetizes me.

a men who is writting

What I don’t like is somebody who puts nothing at all. If you leave your “About Me” section on a transgender dating site empty, you’d probably run into seedy characters who just swipe right to everyone they see.

Think of it like a resume. A little effort goes a long way.

Winks, Likes or Hearts

This feature is usually available in My Transgender Date and it’s the perfect tool to utilize if you’re the shy type.

I for one am used to being afraid of rejection and nothing is more annoying than when you get “seen-zoned”.

smileys and hearts

It probably took weeks before you were able to upload your profile picture and vulnerabilities online then you find your message ignored by some hot chick who’s looking for a 6ft 2 Abercrombie model.

If rejection is something that scares you, you can simply send the girl a:

  • wink
  • like
  • or heart

then wait if she reciprocates. The moment you get a response, start creating a compelling first message which I’ll be talking about in the final section.

Introductory message

You finally have the moxie to send your dream girl a message but you have zero clue on what to tell her.

I’m probably not your dream girl but please don’t ask for a Skype ID on your first message.

Avoid asking a transgender woman in a dating site if she has gotten her boobs done or her noodle size on the get-go.

men in chat

I know that you like s*x as much as I do but get a hold of yourself.

Keep your first message cute and straight to the point. Nothing’s more annoying than a copy-pasted novella.

I don’t need to know everything about you on the first message. Don’t sound like a spam email from Burkina Faso that’s telling me that I can get millions of dollars if I cooperate.

Start with a message like

“Hey, it’s nice to see you here. I’ve been through your profile and you seem very interesting. I would like to know you if possible *insert smile emoji*”.

Keep it friendly, dignified, and sane.

Lastly, avoid wearing statement shirts that say 4:20. I also don’t want to see you vaping on your profile photo.

Dating Transgender Women in Person Tips

If you’re lucky enough to have trans women near you and someone agreed to go on a date, it’s time for you to know what you must do when you’re on your actual date.

Some of the tips that I will be giving you are based on my experience. However, I’m not claiming that I’m the proper representation of a transgender woman.

I’m a bit of a diva so you may find these tips a little bit too demanding. However, when it comes to dating, it’s better to know the extremes. Please take this with a grain of salt.

No CHEAP Dates

Gentlemen, for the love of everything that’s holy, DO NOT ASK HER OUT FOR A COFFEE DATE.

This is very uncouth, lazy, and telling of how disinterested you are with this woman.

meeting with a trans women

When you date someone, be prepared to at the very least, take her to a decent restaurant. Remember, you’re the one pursuing her so you must do everything to give her a great first impression.

If you don’t, she may not see you again. A transgender woman who knows her worth will not waste time with you. Some of them may not even dignify your invitation.

Sleeping together on the First Date is a No-No

I know that I may seem like I’m turning into your mother and you’re my only daughter.

However, please know that this is more for you than her.

Because transgender women are often fetishized and sensualized, a lot of us lose trust in men’s intentions.

empty bed

If you talk about a lot of carnal topics from the get-go, you’re going to be put in the tranny chaser bin. Don’t waste this opportunity most especially if you find the type of girl that you really like. Treat her with utmost chivalry and respect.

This seems quite hard because I know that you love making love. However, Billy, or whatever your name is, you have to play your cards right.

Don’t worry, if you follow the tips enlisted in this section, you’re going to be able to get to that point (rockets, fireworks, butterflies, or whatever you associate to what constitutes great love-making).

Assure Her that You’re Not Ashamed

Nothing’s more effective in getting a transgender woman hooked on you than to have her assured that you’re not going to be ashamed to be with her.

A lot of men who date transgender women want to engage in a secret relationship.

happy couple

I’m not judging these men but realistically, they don’t hold a candle to men who openly date transgender women.

If you let her know and make her feel that you’ll be proud to be in a relationship with her, she’s going to love you more. Trust me on this one!

She’s your EQUAL

You may be thinking that because she didn’t have the same opportunities as you’ve had, her worth is less than yours.

The society has stolen opportunities and dignity from transgender women in the past.

in a relationship with a trans

Sadly, it’s still an ongoing situation. A lot of trans women around the globe are still stripped off from being able to finish school and entering certain areas in the workforce.

This is why a lot of trans women may not be as successful or as cultured as you are. Don’t look down on women like us. We don’t need your pity. Amidst the oppression and discrimination, we still get to live the life that we want and be the women we choose to become.

Living as a woman 24/7 for a transgender woman is already a success. Don’t underestimate us most especially if we get to the point of leveling the playing field. Transgender women have a lot to offer.

You’ll be surprised!


holding hands

You may not be able to remember everything that’s written here. I know that I have a tendency to ramble a lot. However, when all else fails, always know that the best way in attracting another human being is simply by being yourself and treating them with utmost respect and understanding.

It’s unnecessary for you to be the most handsome guy in the room. You don’t have to possess Bill Gates money either.

Just be a good guy with good intentions. Be genuine at all times and most importantly, don’t forget to LOVE.



Posted in Love and Relationships
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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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2 thoughts on “Transgender Women Dating Tips for Newbies

  1. Helpful. Will take it as advice from an expert. Recently spotted the most beautiful profile written in words that could easily have filled a book. And wondered how I could possibly respond to a girl who is ‘in my dreams’ for now. Okay. Advice taken

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