Transgender Dating

Dating a Trans Woman: My Adventures & Advice

I needed a change; the brutal world of dating had left me exasperated. I decided to try something new and fixed up a meeting with a trans woman online. I got to the bar before her. She came on time. She was a statuesque blonde and remarkably pretty.

There was a mix of excitement and anxiety in my voice. We both introduced ourselves and got down to the usual dating talk that I have done hundreds of times before. However, this time the situation panned out differently. In all my dates with women, it was basically me talking about interesting stuff while the girl just sat there nodding her head and giggling. But this time it felt different.

This girl listened to me with undivided attention and kept her smartphone away. She had many humorous stories to tell, and the time passed quickly. She did not put pressure on me to act cool, nor did she give me that judgmental gaze which is a hallmark of cis dating. The night went smooth, and we eventually went to my place. But that is a story for another time.

trans women

Normal is King: Do not be a weirdo. You have to act completely normal and take it easy. Do not ask uncomfortable questions that will ruin the vibe. It is pretty easy to be normal. Just go with the flow and everything will be all right.

Be Chatty: I have had many dates turn awkward due to neither of us speaking or there being long pauses. You have to avoid this. The conversation does not have to be deep; it can cover general topics and be pointless as long as it is fun. As the man in the courtship process, it is your duty to steer the conversation.

Do Not Make Her Uncomfortable: Trans women really have it tough in the world. They are constantly attacked by the mass media and conservative culture for things they have no control over. It is the duty of the man to make her comfortable and not ask questions that make her feel apprehensive. This is actually very easy to do. You just have to accept the lady as a full woman and you will find that this step will come naturally to you.

Transgender dating is as exciting as it is novel. It is one thrill that has to be experienced to be understood. Trans women will definitely rock your world and will give you a totally new experience. The only thing that a man starting out on this journey of Trans dating has to do is to show up with a nice disposition to the date, have an open mind, and look for love. It is simple. It is uncomplicated. It is beautiful.

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10 thoughts on “Dating a Trans Woman: My Adventures & Advice

  1. TansSingle would like to thank you for your in depth comments and observations regarding our terminology on our article. We would like to apologize for what may be or seem to be disrespectful or inaccurate terms. We agree that there are certain tags etc. we should no longer use and will be correcting these immediately. TransSingle welcomes our community to comment and if need be “correct” us. We pride ourselves on providing a safe and comfortable environment for our Transgender community.



    1. It always amazes me that dating sites aimed at dating Transwomen have models on the front membership page that are perfectly cisgender “Cindy Lawford” look-a-likes. Although we would all love have looks and bodies like Cindy Lawford, the reality for many transwomen (myself included) to merely pass as our gender identity and live our lives without being outed is a dream that is far out of reach.


  2. Love to meet trans woman I am a crosdresser behind closed doors who would love to have a trans woman help me dress and have a very serious girl day out in puplic go shopping get pampered like real woman just want this bad


  3. hellow can u skype whit me in love me true im jhen philliphines 18
    if u read this just add me on fb tJ jhon ybanez think u hope u will find someone for me


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