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So you’ve been active on a transgender dating site or ts dating app for a while and finally caught the eye of a trans woman. You chatted, truly enjoyed the back-and-forth, and feel a strong enough connection to take this to the next level.

Yet this is where things tend to get complicated. Online dating is already quite the challenge, but taking any relationship offline can prove daunting, no matter what gender you and your match identify as. The questions remain the same: When is the best time to suggest a real-life date, even at a safe distance if necessary? How can you be certain your potential partner feels the same? If you gathered the courage, how do you phrase your question?

Let’s assume that somehow, you did it. And congratulations, they said yes!

Now the real adventure starts. When you’re dating a transgender woman, you will face more – or rather, different – challenges on your romantic journey.

Your presence on trans dating sites indicates that you already know a bit about trans issues and the reality of transgender lives. However, if you are genuine in your interest when it comes to exploring dating a transgender woman, you will need to do your homework, as they say.

This homework includes research on several aspects of transgender life, including the harder parts and topics you, as a cis person (that is, a person who identifies with the gender they were assigned at birth), might not have on your radar yet. The lack of true and practical information, which may be difficult to come by online if you aren’t entrenched in the community, further complicates your progress.

Fortunately, you have found this guide and thus a great starting point! If you have been wondering what it would be like to date a trans woman or if you have started dating one and need a roadmap to help you navigate the dynamics, the following information will be very useful.

Research and Reflect

Before you begin your search for a trans woman on any transgender dating site or ts dating app, you should take a bit of time to research and understand the various aspects of the transgender community.

Topics we recommend you explore if only on the surface, include but are not limited to: 

– What does trans/transgender mean? How does it relate to the concepts of intersex or the term transvestite?

– What is the difference between sex and gender?

– What are common gender stereotypes and how does the trans community work to dismantle them? What are gender nonconforming practices?

– What legal and medical ramifications are involved in being trans? What role do hormones play? What surgery options are available, and how difficult is it to access them? Who opts for surgery and why, who decides against it?

You do not need to spend too long doing this research before you will have successfully dispelled several myths about transgender lives.

Having at least a basic understanding of these concepts and questions will lessen the burden your future partner or date will have to carry. Just like it is not on people of color to educate their white friends on the realities of racism and ‘Life While BIPOC’, do not expect trans people to enlighten you. Some might be willing to, but the onus is on you to learn.

While doing this research, you might want to reflect on your own experiences. How do you experience your gender? What shaped it? What stereotypes do you maybe harbor? How does this affect the way you approach dating?

Dating a trans woman may not fit your preconceived ideas of dating a cis woman. We assure you, however, that it will be worth the effort you invest in opening yourself up for new experiences.

Avoid Transgender Talk During Your Dates

While you might be curious about your date’s history or details about their life as a trans woman, never make the mistake of delving too deep into the subject of transgender. Just as curiosity killed the cat, it could also kill any relationship potential that was budding between you and a trans woman. It is possible that the subject might pop up later, but in the beginning, it is better to err on the side of caution and steer away from potentially awkward subjects. Remember that, for most people, their gender is an intimate subject, and talking about it with anyone requires trust and feeling secure in the situation.

Even if she initiates the subject at some point, we recommend proceeding carefully. Be careful of boundaries and intrusive questions. However, when she expresses willingness to talk about transgender topics and her own journey, listen keenly and without judgment. Show that you appreciate the trust she places in you and proves yourself worthy of this trust.

First Impression Matters

How you meet the trans woman on your first date may make or break any chances you have of a long-term romantic relationship. Since yes, first impressions matter. Beyond the way you communicate, this also holds true for attire and clothes.

While not every female-presenting person in the trans community values fashion and spends ample time on styling themselves, putting an effort into one’s appearance is a form of self-care. If we feel comfortable in our skin, we will looser and more relaxed when meeting a potential partner for the first time.

You should complement this by putting effort into your dress and maintenance. You do not need to dress up to the nines – but make choosing an outfit an active and conscious choice. Select something that reflects you and your character, don’t ‘dress up’ or pretend you are something you’re not. Natural charm goes a long way and shows your date that you are genuine in your interest.

Be a Gentleperson

Some transgender women enjoy presenting even more feminine than their cisgender counterparts. Other trans women may act more genderneutral or be actively nonconforming and/or fluid. Regardless of how they present, be a gentlemanly date. Not in a condescending way, but from a place of deep respect.

Whether you are a cis man or a cis woman and about to date a transgender lady, you can be courteous. Chivalry, in the sense of pulling out chairs or opening doors, might have a very positive effect on your date. However, only do this if it fits your personality and style. As with clothing, there is no need to pretend you are something you aren’t. Engage your date in meaningful conversation, truly listen when she talks, and smile so that she sees you enjoy her company.

Be Prepared to Talk Politics

For many people in the transgender community, politics is an important subject. The government decides who can transition from one gender to another, whether or not there are gender options outside the binary of male and female, how easy access to hormones or surgery is, and how protected we are in our everyday lives.

While ‘Keep away from politics’ may be sound dating advice for some, when it comes to being active on a ts dating site, you should be prepared to engage in political debates.

This advice ties in well with the research homework you have been given already. Unless they know someone personally, most cis people are unaware of the legal aspects and challenges of being transgender. If you educate yourself, you will certainly impress your date by showing interest and communicating that you are genuine in your pursuit of dating a transgender woman.

When It Comes To Sex

… be patient. Taking one’s time is a good idea regardless of gender identity, since building a long-lasting relationship depends on so much more than sex.

For some transgender women, sex can also be a difficult topic. Not every trans woman had top and bottom surgeries, so do not assume you know what your date’s body looks like underneath her clothes. Once you have built a foundation of trust and you both feel comfortable in each other’s presence, you may certainly ask your date about their sex life. Share your own experiences, if you think it might help. Showing your partner that you are open to talking about intimacy will go a long way in making her feel respected and safe.

Communication is key here – never assume anything. Many trans dating sites offer the option to specify operation status and more, yet this does not mean every person experiences this the same. The wonderful thing about human sexuality is how varied and colorful it is. Explore with curiosity and an open mind. Don’t set yourself any expectations to meet, or signal your transgender partner that there is a certain way they have to perform in order to earn your affection. 

After all, you are dating a transgender woman from a place of love, on a quest for belonging and connection. Neither one of you is in this for a quick hookup - there are other ts dating apps for that.

While there are certainly more tips that will help you navigate the trans dating experience, this hopefully proves a useful guide and starting point. Now off you go, be brave, and make a move!