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Ladyboy Dating Drama

Amanda Valentine Dela Cruz
This post was last updated on .

Drama is everywhere and not just in the world of ladyboy dating but I’m going to list some possible scenarios and how to deal with them.

If you find yourself giving up because of the drama, toxicity, and exhaustion, please keep reading.  I’m a ladyboy and the stuff I’m going to include will be from experience through myself and with friends.  Alright, let’s start with…

Your Current and Your EX are FRIENDS

Boy oh boy… this really sucks lol.

Your current ladyboy date is friends with your ex and you found them both in the same ladyboy dating website.  I’m pretty sure that you and your date are both aware of the girl code and the bro code or whatever they call them these days.  To be honest, this is a really sticky situation.  If this ever happens to me, I think the best way to deal with this is to wait for some time (around 6 months) before having a conversation with my girlfriend.  6 months is a good gauge to knowing if the relationship is serious and going somewhere.

However, if your relationship with your ladyboy ex ended up badly and you’re the one at fault, your current ladyboy date should be prepared to lose the friendship.  All in all, I don’t want to be in this situation but if the LOVE is too strong, maybe you could make it work

Your Family and Friends are Transphobic

I suggest you get a new set of friends, parents, and siblings. Seriously, I do.  LOL  Anyway, this will all depend on you and how much you want your relationship to grow with your ladyboy date.  To be honest, even if I’m a ladyboy, I have to sometimes compromise and endure a little bit of abuse in order for the future to be brighter with the one I’m currently dating.  Let’s factor the guy’s inheritance, promotion, or closing a huge deal lol.

If you’re a ladyboy and your boyfriend asked you to give him a little more time before going public with you, I think you have to take a little chance.  Just be sure that he truly has a plan and not just stringing you along.  However, if your boyfriend is just too concerned just out of not wanting to be criticized and doesn’t acknowledge your relationship with him even after many years of being together, he’s a COWARD.

Give yourself a deadline and a timeline sis!


This actually happened to my friend and I don’t want to judge anyone’s relationship.  So my friend is planning to be post-op and she’s disgusted with the thought of having a penis.  Her boyfriend likes the best of both worlds but they remain together because they have a great connection.  However, my friend compromised and she’s OKAY with her boyfriend having sex with other ladyboys and he often watches ladyboy porn in front of her or while they’re doing the deed…

Again, I am no one to judge.

They seem very happy as they’ve been together for years. If you find yourself in a situation like this, maybe you can go with the open relationship kind of route. I’m not advocating infidelity but sometimes, something’s got to give.



Posted in Love & dating

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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One thought on “Ladyboy Dating Drama

  1. ” However, my friend compromised and she’s OKAY with her boyfriend having sex with other ladyboys and he often watches ladyboy porn in front of her or while they’re doing the deed”

    So sorry for your friend. She needs a man who can be happy with just her. Removing her penis will solve nothing. Hope she is careful and uses protection if she continues with him (boyfriend)

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