Talking to Trans Women on Dating Apps – Key Tips

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Alan Schin
Updated on December 19, 2024 | 15 min read
Talking to Trans Women on Dating Apps – Key Tips

One thing for certain – there is no lack of online dating apps out there. Reportedly, there are about 8,000, with new ones popping up every day. There are the huge apps that try to be everything to everyone; there are very small apps targeted at a specific niche of daters – farmers, vegans, astrological signs, gamers, etc.

And yes, there are transgender dating apps too. Trans women and men do access these niche apps to see where they may find fellow members from the transgender community and feeling safe within that community.

On the other hand, these dating sites can be a bit restrictive if a trans girl wants to connect with others based on her sexuality. For these connections, trans women may want to think about using a broader dating app that encompasses the larger LGBTQ community. For example, suppose a trans woman may want to connect with lesbians, gay men, bisexuals or other non binary people. An all-inclusive, user-friendly LGBTQ+ dating app allows this, in a safe environment where they can be who they are openly and without concern and seek connections, bonds, and yes, romance, and to freely seek love.

If you are looking to date trans women, and you have not before, then you have some education in front of you before you begin to talk to them on a dating platform. So, let’s get that out of the way – the sooner the better.

How Do I Talk to Trans Women on Dating Apps?

The short answer? You don’t, until you have taken a short master class to learn as much as you can about transgender people, and specifically trans women. It’s not like dating a type of person you have dated before that allows you to just move on in and start chatting. Trans people are unique and enter the dating world with far different experiences than others have had.

So, where do you go for this master class? Several places actually.

  • There are plenty of websites and chat forums you can access to read up on trans people. If you join a forum, spend time taking in what trans women say about dating and finding meaningful connections with others.
  • There are LGBTQ dating sites with transgender members that also operate as their own social media function. Join one that seems to be popular. If it doesn’t have groups to join, there are other dating sites that do. Keep looking until you find one or more apps where trans singles gather to post and participate in discussions. Be a listener not a talker. You are there to learn, not to look for a date yet.

In the meantime, here is some general information about trans women and what they bring to the table, as well as some important dos and don’ts as you talk with them on a trans dating app.

Some General Information About Understanding Transgender Women

You need to understand what makes trans people unique, so here is the most important basic information.

Everyone is assigned a gender at birth – male or female. Some feel uncomfortable with their assigned sex very early on. They may be in a male body but have the same interests and tendencies as girls. They reject societal norms about how to be a boy and grow up feeling very uncomfortable and even distressed about their body. This is known as gender dysphoria. Add to this the fact that many see trans people as deviant, mentally ill, and dangerous, and you understand why a trans woman may not be open about her identity in public spaces. And they bring this “baggage” into dating relationships.

Difference Between Gender Identity and Sexual Orientation

Trans women are females born into a male body. This is how they identify their gender – female.

Gender choice is separate from sexual orientation. A trans female may be lesbian, bisexual, non-binary, pansexual, as well as any of a myriad of other things – aromantic or asexual, for example. If she joins a dating app, it will be because she is looking for a safe and secure environment and to have a dating experience, perhaps to find the right person for a serious relationship. She’ll join a trans dating app or

Cisgender women are those who identify as the gender they were assigned at birth – female. In terms of sexuality, they may be straight, lesbian, bisexual, etc. And they may join a dating site where they will find who they are looking for in the type of relationship they want. A straight cis female, for example, will be looking for cisgender men who are also straight. She’ll join a dating site that caters to heteronormative people.

Trans Women Are Often Objectified

What does this mean? It means they are treated by others as a thing rather than a whole three-dimensional human being. Their being trans becomes their only defining feature, and men may use them for another “notch in their belt” of sexual conquests or because they have a fetish. It is no wonder, then, that they are mistrustful when any man begins to show interest but does not seem to be interested in her other than the fact that she is a trans female. If she is on a dating app, she is not likely to respond to men who want to address what it feels like to be her identity in initial communications. Here’s an example: She and a man begin to chat on a dating site. His first question is if she is in any stage of transition and, if so, what stage. Her response will be to block him. This topic has no place in initial conversations.

Trans Women Fear Rejection

A transgender woman worries about rejection because she has experienced it in her lifetime. She may have come out to family members and been rejected and condemned. She may have faced discrimination via local and state laws that don’t protect the trans community. She may have had more than on dating experience that ended badly by being dumped because her boundaries were not respected. It’s no surprise that she has trust issues. Before you begin ts dating, you better be sure of your motivations, and they better be honorable.

Now that you have a much better idea of gender identities vs. sexual orientation and the issues and challenges that trans females deal with in their world, it’s time to look at strategies and tips for talking to them in a dating app environment.

How to Chat with Female Trans Members on a Dating App

How to Chat with Female Trans Members on a Dating App

Here’s a news flash. Transgender women are three-dimensional people. They have careers/jobs, education, goals, values, hobbies and interests, and causes they support.

Think about how you would take the lead in a conversation with anyone who has struck your fancy on a dating app. Would your first question be what her favorite type of sex is? Of course not. And if you ask a similar question of a trans women, then you are objectifying her and need to go away. All other trans people will tell you this. Come back to the app when you have educated yourself and gained the right perspective.

So let’s talk about the “do” questions and topics for conversation with trans women.

The Right Questions and Topics

The key in the early connection with women of any gender is to keep it light. Early chatting should be fun and engaging, not to mention respectful. Not every transgender dating app will have these, but many of the larger LGBTQ apps do – they’re called icebreakers. And these are light-hearted questions that will put anyone at ease. Next should come questions and topics about job, hobbies and interests, etc. Deeper questions about values and goals come next; and finally, getting into the realm of sexual topics.

So, you’ve got 4 levels of questions and topics as you chat online with transgender women. Let’s look at some examples at each of these.

Level 1 Questions

So, you have just met online and have greeted one another. Now what? Here are some examples that keep things light and get your chat partner to relax and feel at ease with you. Having fun is the first step in building relationships with transgender women and getting them toward a feeling of safety chatting with you.

  • Describe yourself in one emoji – I’ll start – here’s mine
  • What’s the strangest food you’ve ever tried?
  • If you won the lottery, what’s the first thing you’d do?
  • What’s the best trip you’ve ever been on?
  • It’s Saturday, and you are totally free. What do you choose to do?
  • If you could be your favorite character in a TV show or movie, who would it be?

You get the idea. These types of questions are all over the internet – find engaging ones and use them. Here’s another engaging and enjoyable first chat activity – this or that.

“Let’s play this or that. Are you up for it?”

  • Steak dinner at a high-end restaurant or takeout Chinese?
  • Early bird or night owl?
  • thrift shopping or online shopping?
  • Livestreaming or cable TV?
  • Books or movies?
  • Work for yourself or for a company?

Again, these are all over the Internet – find those that interest you.

The key here is to have fun with your new chat buddy and to make her feel free and easy with you.

Level 2 Questions

Here, you want to get a little deeper into their lives, but not too deep. These questions give each of you insights into the other’s personalities. Be prepared to give your answers to the same questions.

  • What do you do in your free time?
  • Is there a special cause that you are passionate about?
  • What’s your fav thing to do in your free time?
  • Do you like your job? What would your ideal job look like?

Again, this is treating your newfound trans interest with respect for her multi-faceted life. And she will feel totally free about answering these questions. She knows you are interested in more than her genitals and sexual activities.

Level 3 Questions

Now you are ready to get into some chat about some deeper subjects but not about sexual things yet. If you have made it through the first two levels and she is still with you, you get a gold star so far.

  • Where do you see yourself 5 years from now?
  • How important is religion to you?
  • Do you consider yourself a liberal or a conservative?
  • Are you an idealist or are you more practical in your approach to life?
  • How do you handle setbacks and challenges?
  • How do you define relationship success?
  • How important is communication in a relationship?

You are still probing for deeper insights here. And she will appreciate that you want to know and understand her on a deeper level. You’re doing great so far!

Level 4 Questions

Here’s where the whole sex thing comes into play. If she has stuck with you so far, she has a high level of trust and is probably willing to chat about her gender identity, her status in transition (if any) and her expectations and boundaries in sexual activity. Be prepared to disclose your expectations and boundaries too. The keys here are honesty, openness, and respect.

  • Are you willing to talk about previous sexual experiences? If so, what were the best and the worst?
  • Are you in any process of transition right now? Where are you in the process? Hormonal treatments? Surgical status?
  • What are your expectations and boundaries related to sexual activity? Here are mine.
  • How important is foreplay, communication during sex, and the afterglow following an encounter?
  • Do you feel objectified? How can I help you overcome that?

These are more invasive questions, so tread patiently and let her take the lead. Make sure you tell her that if she feels uncomfortable talking about any of this, she is free to take her time and simply tell you she is not ready for that conversation yet. Being transgender is living in a complex world.

When you get to this point in the conversation with your trans female partner, and she is responding with openness, you have reached the point of a solid bond. And it’s probably time for in-person encounters.

As You Move Forward in Your Relationship

You have now progressed to a stage in your trans woman partnership that many others do not reach. This trans person trusts you, has revealed a great deal of intimate knowledge about herself, and is also ready to move forward as you are. What a great place to be! Many transgender people don’t experience this.

But now, it is time, as your alliance grows, to show a strong commitment to transgender people in general – trans men, trans women, and other non-binary people who exist and identify along this spectrum. Trans dating goes well beyond just dating.

What can you do to show your support in a world that too often de-legitimizes trans men and women via transphobia ajust downright disdain and hate?

Become an ally. Call out transphobia and hate whenever and wherever you find it. Join organizations promoting the health and well-being of trans people as well as serving to educate and inform the public. Take part in events and celebrations with your partner. The transgender world needs you and your support – all trans women and guys, not just your transgender woman.

Let’s Recap

Transgender dating takes a commitment, patience, and a respectful approach at all times. You must move up the line of talking, through these levels, and that takes time. You now know how to proceed and what not to do as you. She needs to know you are willing to go at her pace, not yours. What you are building is a partnership in which you both feel free to express yourselves about anything without fear of judgement or rejection.

Now, a Word About Online Trans Dating Options

You need to look for trans dating apps that are safe and secure – one that the transgender users are fully comfortable with. And you want that for yourself too. Here are what you should look for:

  • A stiff and rigorous verification process
  • A free and premium membership, in case you prefer more features.
  • Written policies and procedures to protect the privacy and safety of all users
  • Guaranteed privacy for conversations
  • Social groups that users can join and join in with emotional safety
  • One that practices the firm commitment that “all our members are worthy of being honored and celebrated not matter what their identity or orientation” and demonstrates that in its features, its articles, and its customer support.

Some apps do a great job of this; other apps do not. Choose wisely.

Concluding Comments

Trans dating and building a healthy partnership with a trans female requires effort, time, patience, and a willingness to move along on her terms. As you build this partnership, keep working on understanding her story and what it means to walk in her shoes.

Communication is the key here, as it is in any close and successful romantic partnership. Transgender dating is like any other kind of dating – a commitment to growing and learning about each other. A trans person is multifaceted just as anyone else; ts dating needs to progress just like any other dating; and transgender dating, if done right, results in you and your transgender person enjoying an exciting and fulfilling life together.

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Alan Schin

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