Skip to content

Dating a Famous but Discreet man

Amanda Valentine Dela Cruz

Today is going to be an article solely for my trans sisters. Transgender dating is already a very small circle made smaller by dating sites.  Dating sites are the most accessible avenue and common ground of trans people and people who love them so it’s inevitable to be passed by popular personalities from time to time.

Dating famous people can be rewarding but can be crippling to one’s confidence at the same time especially if you’re a transgender woman and the man you like who also happens to like you back can’t for some reason introduce you to the world.  I’m a very understanding woman and I try to be patient for as long as I can especially if LOVE is already in place and for the welfare of my partner.   However, there comes a time when I’ll tell myself…

Enough is ENOUGH!

Well… factoring if he makes millions, that’s a whole different story. Just kidding!

When is it ENOUGH?

For me, a good gauge is usually 6 months or when the time comes that I start doubting myself.  Doubt in a way that it’s already affecting my view of self-worth.  When my confidence escapes my individuality and I’m starting to think that I’m less of a human being just because I’m transgender; that’s when I think I’ve had ENOUGH.

How is it ENOUGH?

Please keep in mind that there are different types of men.  These men have different approaches as to how to deal with their transgender dates.  Some men are so smooth and can get you thinking that you’re doing something noble by keeping your relationship a secret.

To cut the story short, you’ve been DICKMATIZED.

I’m sorry but I can’t find any other word to describe it.  You’re the only one who can really assess the reality of what type of relationship you’re participating in but it’s pretty obvious that you’re only being manipulated if his wants and needs are the only factors that are being fed in the relationship.

Why is it ENOUGH?

I don’t know your situation and why you’re still in this relationship.  I also don’t know if the discretion will end and you’ll get to live happily ever after with this famous man.  All I know is that time’s-a-ticking and you’re not getting any younger.  Most women and I’m not discounting myself, dream of a knight in shining armor and we sometimes think that a dashing and rich man is the epitome of that but… is he really a knight if he can’t defend you let alone introduce you to his circle?

I don’t want to shatter your dreams but if you prefer to live a life of secrecy, that’s all on you.  Maybe your LOVE for him is too strong already or maybe you’re benefiting in different ways but ask yourself this…


I used to work in the adult industry and have dated very powerful and popular men in the past.  Why am I here single and writing about not recommending a relationship like I’ve had with them?  I’m not saying this out of bitterness, I still have feelings for some of them up to now.  Sure, there are a lot of perks.  Expensive gifts, gratified attractiveness level, and fancy restaurants…

I just think, even if I’m single, writing this transgender dating article, on the work desk in my bedroom which is so far from a glamorous life, I get to at the very least sleep comfortably at night knowing that I AM WORTH loving and there’s nothing nagging me about how I should feel guilty of being in a relationship which can potentially ruin someone’s career and livelihood just because I’m a transgender woman.

At the very least, I’ve let go of them because guess what? I know LOVE and that LOVE began by letting go because I LOVE myself too much not to hurt myself furthermore.

Find a REAL man, not the FANTASY.



Posted in Love and Relationship, Product updates

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 ->

Related posts


Leave a Reply

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