My Ladyboy Cupid

Dating tips when you meet a ladyboy online

Finally… after meeting a beautiful Ladyboy on MyLadyboyCupid and “dating” her online for the last two months, today is the big day.

Create a FREE profile

Finally, today you are going to get to meet her in person. You may be living in Thailand or The Philippines already or might have traveled to her country to meet the Ladyboy you’ve been longing to meet.

It’s your first real chance to get to know your “date” in the flesh as it were. The first chance to meet your potential Ladyboy lover. Of course, you want it to all go well, your first true meeting to proceed smoothly. Hopefully, you will “bond’ and this will be the beginnings of a special long-term relationship…

Meeting a Ladyboy you’ve been “dating” online for the first time

Nervous: probably. Excited: for sure. Looking forward to meeting the Ladyboy you feel that you’ve known for longer than the two months you have been talking, flirting and dating: absolutely!

First dates are always quite stressful whether they be with a genetic woman or a Ladyboy. You want everything to go well, the conversation to flow naturally and both of you to have a great time. But most of all you want this to be the first of many dates and the start of your life journey together. After all, you’ve had two months before today to get to know each other reasonably well!

A short selection of great dating tips when dating a Ladyboy

We could offer dozens of tips and suggestions about what to do on your first date with a Ladyboy. But, let’s keep the number down and aim for just 6 great, important tips to make her feel comfortable and relaxed:

  • when you see her, compliment her on her looks, her choice of clothes, her hair and her choice of clothes. Nothing makes a woman feel as good about herself as compliments. Make sure you sound genuine and sincere in your compliments (you will probably be when you see your beautiful Ladyboy for the first time!).

But don’t forget to remark on how good she looks every time you meet. It’s doesn’t have to be specific comments each and every time. “You look great!” will suffice most times; or try “Your dress really suits you… makes you look wonderful!”

  • tell her she’s beautiful: this can be an adjunct to the point above. But Ladyboys love to hear that they are beautiful. In fact, your new Ladyboy girlfriend most likely is a stunner with high cheekbones, full lips and long dark/black hair. Just remind her now and then that she is a true beauty…. flattery can get you far!

Charm your Ladyboy girlfriend, just like you would any other woman

  • buy her surprise gift or gifts: maybe just a small token gift for the first date (perfume, chocolates or a bracelet). It’s not something you have to do every time but if you go shopping just buy your Ladyboy something she admires. Or buy it when she is not with you and keep it to surprise her next time…. Thai Ladyboys and Trans-Pinay are suckers for gifts!
  • it may not be on your very first date and perhaps more something to keep in mind for future dates (if your dating and relationship gets that far, of course). You’ll invariably meet some of her friends and, in time, she will meet yours—again especially if she is Thai or Filipino and you are already living in her country. Whatever you do, when you do introduce your Ladyboy girlfriend to your friends, don’t call her a Ladyboy, Katoey, Trans-Pinay or anything which signifies she is not a “real” woman. Have some respect for her and the challenges she has had to face growing up different from others. She is forever striving to be a woman, not a Ladyboy!
  • this last point leads neatly into this one: at all times, whether alone with her at home or out with friends, treat her just like any other woman. Forgive her moods and her (perhaps childish) behavior, forgive her temper and emotions. Underneath it, all your Ladyboy is fundamentally a woman, with all the challenge which go with the territory. Something you need to always keep in mind!

Finally, when dating Ladyboys: be polite and respectful

  • this piece of advice shouldn’t really be on the list, it’s really only common sense. But you’d be surprised how many Trans-oriented men on MyLadyboyCupid think it’s okay to ask a Ladyboy they’ve just met about their surgeries or lack thereof. In short, don’t. Don’t ask invasive questions on the first date, unless your Ladyboy friend volunteers the information.

Does it really matter what operations she has had if she’s young and beautiful, you’re happy and she is dating you?

The best Ladyboy Dating site © 2023 MyLadyboyCupid