As a transwoman, dating can be a challenge, and can often be an uncomfortable experience. At MyTransgenderCupid, we’re hoping to change that. Our goal is to connect men with transwomen and help them find love. Some men are excited to start on their journey of dating transwomen, but they may not know where to start or what to expect. If you’re the lucky gal that gets to be a man’s first experience with dating transwomen, we want to make sure you have some good advice to help make this as fun and easy as possible. Dating is supposed to be exhilarating and exciting! We don’t want you to be worried and stressed out about what to expect. That’s why we’re giving you some tips and tricks for going out with a man who’s never dated a transwoman. Let’s get started!

1.    Be Safe When Dating On Transgender Datingsite

Unfortunately, transgender individuals are disproportionately affected by violent crime, and due to this, trans people often must take extra measures to ensure safety. By taking safety measures before your date, you can relax and enjoy yourself instead of being on edge the entire time. Your safety should be the top priority every day, especially while dating. We want to give you some practical things to consider to help make your date as enjoyable as possible.

  • Conversation safety

So, you met a guy online and you’ve started talking. Great! Maybe there’s some flirting, and some questions being asked to help you get to know each other. This can often be a fun, exciting phase in the relationship, but you should still make sure that you are staying safe even if you are only talking. Do not give away any sensitive information to someone you do not trust. This is a great time to talk about being out and how comfortable you are with people knowing you’re trans. Protect yourself and your information and set boundaries with the man you’re talking to. 

  • Plan to meet in a public place

Especially if this is the first time you are meeting in person, ensure that you’re meeting in a public place where you feel comfortable. By meeting in a place where you are comfortable, you’re allowing yourself the freedom to enjoy your date and not worry about being in a new, uncomfortable setting.

  • Tell someone where you’re going.

Before going on a date, make sure that someone you trust knows where you are going, has a picture of you in the clothes you’re wearing on your date, and when they can expect you to get home.

  • Know your exits

If you have been to this location before, you should already be familiar with how you enter and exit the place, but if it is new, take some measures beforehand to make sure you will be safe throughout your date. Scope out the place before the planned meeting time. Whether you swing by a few days before or plan to arrive early, make sure you know where and how to safely leave the place you are meeting. If you feel unsafe or threatened in any situation, do not hesitate to leave. Don’t worry about coming across as rude, your safety is more important than manners.

  • Sexual safety

If you are sexually active or planning to be, it’s your job to ensure you are protecting yourself from any STDs, or STIs that may be transmitted during sex. Always use protection when having sex and get tested periodically if you remain sexually active.

Whether you’re just texting back and forth, going on your first date, or having intercourse, your safety is the most important thing to consider. It’s unfortunate that transgender people are at higher risk of violent crime, but we are here to help you find practical ways to ensure your safety and save you some peace of mind throughout the entire process.

2.    Be Patient with TS dating

A little patience goes a long way with TS dating, and you’re probably going to need some if the man you’re dating is a first-timer with a transwoman. He may not understand everything about LGBTQ+ issues, and he will probably have questions. Be patient with him as he navigates this new territory and learns about the transgender world.

  • Don’t immediately assume the worst

If he uses words that are not inclusive, don’t automatically assume he is transphobic or homophobic. It’s possible he is just ignorant of inclusive language, and this could be a great opportunity to teach him. If he uses words or phrases that are offensive to you, feel free to point this out and explain why these words can be hurtful, and offer suggestions for what he could say instead.

Of course, some transwomen prefer to be with someone who is well-versed in LGBTQIA+ terminology, and they may not want to teach someone everything about queer issues. If that’s not your jam, feel free to walk away. You do you, girl!

  • Answer questions you are comfortable with

If he has questions that you are comfortable discussing, answer them! If he’s never been with a transwoman before, he may be confused or curious about some things and that’s okay. However, if there is something you are not comfortable discussing, feel free to set that boundary and tell him that you do not want to talk about that topic.

If you are the first transwoman your date has been with, you may need to be patient while he learns about you, and the trans community. This can be new, scary territory for some men, and having a little patience can help them feel more comfortable and give them an opportunity to learn things they never would have learned without dating you.


3.    Respect For Transwomen And Men

Just because your date is attracted to you, or likes you enough to go on a date with you, does not mean he respects you. Even if you are the first transwoman your date has been with, he should still be respectful of any boundaries that you set.

  • Name and pronouns

If he is aware of your name and pronouns and intentionally does not use them, this should be a red flag. Your date should always respect the way you prefer to be addressed, and chances are, if he doesn’t respect these basic things, he will likely not respect anything else about you.

  • Respecting your body

Your date should also respect your body and personal space. If you prefer not to sleep with someone on a first date, he needs to understand that and not be pushy. If you are at the point of sleeping with each other, he should also respect your preference in the bedroom and things you may or may not be comfortable with.

  • The way you address your body

A lot of trans individuals refer to their bodies in different ways than most people, especially their genitalia. The man you are dating may not be familiar with these terms at first, but after you have told him your preferred terms, he should be consistent with using those words correctly.

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An important thing to note about respect is that it goes both ways. If you expect your date to be respectful of you and the boundaries that you set, you also need to give him that same respect as well. If there is something he is uncomfortable with doing, make sure you are also maintaining his boundaries and giving him time to adjust to the new territory of dating a transwoman.

Dating as a transwoman is not an easy thing to do and it can be particularly challenging if you’re dating a man who has never dated a transwoman before. Even though this can be scary and difficult, there are plenty of wonderful men out there looking for women just like you.


As a proud transgender woman, I'm an award-winning blogger blending my unique life experiences with a Bachelor's degree in Communication. Known for my linguistic expertise and dynamic writing style, I specialize in CBD, SEO, music, technology, and digital marketing sectors.