Overcoming the Worry About Dating Trans Women in Public

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Alan Schin
Updated on January 31, 2025 | 14 min read
Overcoming the Worry About Dating Trans Women in Public

Decades ago, mixed race couples faced stares, looks of disdain and disgust, and plenty of headshaking on the people when they went out in public. In fact, until 1964, many state laws made interracial marriage a crime. Richard Loving and Mildred Jeters made history when they appealed the Virginia law to the Supreme Court and won.

But federal law did not end the social stigma they faced in public. Years later, lesbian and gay couples began to show their relationships with public displays of affection, again, and still today, facing the same stares, looks of disgust, and headshaking.

This is what it looks like when a society rejects what it sees as non- normal and not healthy relationships.

Now, let’s move on to another type of dating in public – a cisgender man and a transgender woman. And as a man in this situation, you may be feeling discomfort and asking yourself, “How do I overcome being worried about dating trans women in public?” What you have to realize is that she can sense your discomfort, and that only adds to her feelings of dysphoria and rejection.

Life for Transgender Individuals

The transgender community faces discrimination and disdain all across the country. There are state and local laws in at least 24 states that allow discrimination in employment, housing, education, sports, and healthcare. The transgender experience in so many instances is challenging at best and downright dangerous at worst. And the impact on transgender people is a mental health issue.

And as much as trans people try to foster acceptance by society, they face hostility and even violence. Trans women cannot even hold storytime in libraries without frightened mothers scooping their children away for fear that they will be turned into little trans people. And books that have transgender people for characters are now banned from school, again for fear that children will be turned into little transgender people.

At other times, well-meaning people who think they are tolerant and accepting will inadvertently give backhanded compliments, like “You really seem so normal, I never would have guessed you’re trans.”

Of course, all of this is based upon complete and total ignorance of transgender life, but trans people have to live with it every day. And it can lead to gender dysphoria and worse. Trans life is just not as easy and smooth as that of the majority of both straight and other queer individuals.

And here you are, a cis male or female, wanting to connect with a trans woman. Perhaps you met her at a social event; maybe you hooked up on a dating app; possibly you are in school together; you might have been introduced to her by some other woman or man who is an ally and thinks you two would be a good match.

Whatever the method by which you met, you are now attracted to each other and want to explore if a potential relationship might be in the works. But that requires not just talk, but actual dating. Now you worry about how you feel being seen in public when out with her.

And that’s just what this article is all about. There are steps you can and must take if you desire and intend to date transgender women.

Getting Your Priorities Straight

Any woman you date seriously deserves your respect. Think about the cis women you have dated. You have shown regard for their feelings, wishes, and rights. You honor their boundaries and try to meet their expectations. And you enjoy going out to places and events you both enjoy. You take her around your friends. Perhaps she has met your parents. In short, you have no problem being anywhere in public with her.

Now think about how you are dating this new transgender person you have connected with. You both feel the attraction, even if you have only met online, and are now ready for in-person dating. All of a sudden you have some fears. What if you take her on a date to a public place, and others realize she is a transgender person? Will that be embarrassing to you?

Transgender people are used to being stared at; transgender people are used to being dismissed as unworthy of respect and acceptance; transgender people are used to being scorned and being victims of foul language and even violence; transgender people do fear for their safety if they are “out there” all by themselves. This is the reason they tend to remain within their transgender community when they go out in public places. Their own experience tells them this is both physically and emotionally safe. And when they venture out on a date with a cisgender person, of course they are nervous and perhaps somewhat afraid. Their mental health could take another hit.

What is your role in all of this if you have a date with a trans woman? Are you willing to show her the respect and acceptance that you would show any cis women you are or have dated? If not, then you need to slow down, do some real self-analysis, figure out what your hang ups are and then take steps to get over your worry.

Strategies and Steps to Overcome Your Worry

You have an attraction to this trans person, and she is attracted to you. How much do you really know about transgender people in general and about her specifically? Obviously, you have been chatting, maybe online, but you may not have gotten too deep into who she is, who she wants to be, and her own sexuality. So, here are the things you should do.

Do Your Research

If you don’t know a lot about transgender people, now is the time to do some deep research. There are sources all over the Internet. As well, you can join some chat rooms, forums, and support groups to learn more about the challenges and issues they regularly face. You don’t need to actively participate in these groups, but do a lot of listening and ask questions if you need clarification. Ask for advice as a cis person dating a trans person. You’ll want to gain insights into what it means to be trans and what life is like for them as they function in their daily lives and in relationships. And you’ll come to understand the difference between gender and sexuality. Check out as many resources as possible and learn as much as you can.

Spend More Time Chatting with Her

You may know about her school background, her job/career, her outside interests and hobbies, and even her goals and values. But this may be the time to delve deeper into her sexuality. Do you approach the subject without asking first?

If you have developed a trustful relationship with her, it is likely she will be willing to talk about transgender issues in general and her experience, what her life has been like living transgender, from childhood into adulthood, and where she is in the process of transition, if at all. Chances are, if you have seen her photo or had video chat with her, you have some idea. Ask before you pose questions, and make sure you tell her that she should not feel pressured to answer:

  • When did you discover your gender identity? How did you know?
  • How was life pre-transition?
  • Are you in any stage of medical transition?
  • What is your idea of a good relationship with me?
  • As a transgender person, what is your biggest fear?
  • How do you deal with discrimination in public?
  • What kind of support do you want from someone you are dating?

All of this talk will help you gain more insight and determine how you can support her in a relationship and if you should be confronted when on a date.

Spend Time Honestly Assessing Your Own Fear and Discomfort

What exactly are you afraid of in this relationship situation? Is it strangers, family, friends seeing you in public with your new woman? Will they suspect her gender identity and then ridicule you to others?

Well, first of all, do you intend to announce that she is transgender when you enter a club, a social gathering, or a restaurant? Of course not. If you run into family members or friends, are you going to say, “This is Sheila, my date. She is transgender, by the way.” Of course you won’t. If her being transgender is your primary thought about her, then you shouldn’t be dating her anyway. You’ll only hurt her and damage her mental health further.

Addressing Friends, Family, and Others

Strangers don’t matter. And your friends and family deserve the right to get to know her as a person, not as anything else. You and she decide when and how to inform others of her gender identity and that she is transgender. And then together you decide how to educate those significant others who don’t understand.

Some will understand and wish you two a good life together. Others may not. They will insist that a real man would not date transgender people. You will need to decide which is more important – your relationship with this amazing woman or those others who are still steeped in discrimination and judgment. Seek and take your own advice on this matter. The best course of action? Hang out with those who understand and support. Avoid the others, at least for now.

Remember this: Most people, even transgender people, place too much emphasis on what others think. It’s something all of us deal with from time to time. When we overcome this, we are on a path to a far more independent life.

Move Gradually into Dating

There is no reason that a first date must be a public situation. If you have courted her right, she will feel safe with you in any circumstances. How about having some couple dates doing things privately?

Invite her to your place for cooking a dinner together and spending an evening binge watching a show you both love. Dates like this allow you both to get to know one another as friends before moving into the intimacy of sex. She will appreciate that you want to get to know her as a multi-faceted person. Transgender people always worry that their life apart from their gender identity as being trans is not recognized and respected. When their whole lives are honored, they know they have the support they need.

How about a weekend getaway? This will speak to your commitment to the relationship. Will you have sex during this romantic time together? Probably. And once that happens, the two of you will be involved on a new level. Beyond that, you will be together, as a couple, in public places, and in the presence of strangers. You’ll begin to develop a comfort level of being in public with her, once that weekend is over and you return to your own digs.

Finding ways to just relax and enjoy one another’s company will go a long way in solidifying your relationship, and you will begin to feel much more at ease as time progresses.

Be Honest and Open About Your Worries

She is probably already aware of your discomfort. Transgender individuals can sense this and have learned to be aware of this in their lives. If you try to hide this, she will be hurt because you are not open with her.

Speak about your worries honestly. Apologize to her. And even ask her if she can help you overcome the perceived reactions you may get from others in public places. Remember this: relationships cannot progress without full honesty.

Let her take the lead in her response to your fears. Dating men with similar worries may not be new to her, and she can probably give you an example or two of how they may have overcome similar worries.

Being in Public in Your Normal Environment – Try Group Dating

If you have taken all of the suggested steps with your trans woman that are listed above, do another self-check. If you now feel comfortable being in public with her and are ready to have the kind of dating relationship that couples have, arrange a group dating situation with other men and women who support your relationship, who do not see your woman as trans but who want to get to know her as the multi-faceted person she is. Here is an example or two of unique and fun dating ideas:

Go out to dinner as a group, attend a concert where people of every gender and sexuality will certainly be present, schedule an escape room adventure, or a paint and sip evening. The point is gender will not even be a factor as everyone just has fun together.

The other point? You will become more and more confident and ready to go on solo dates. And you may feel ashamed that you ever worried about being out and about with your trans woman. You are now a couple enjoying all of the things that couples do.

In the End…

Being trans isn’t easy for anyone. And being with a trans person may first bring about worry and issues on the part of both of you. Working through them in an atmosphere of full honesty is the only way to go.

But you have now made it! You now have a great understanding of what it means to be trans in today’s world; You have connected with an amazing trans woman; you have deepened that connection and are on your way to a longer-term partnership based on honesty, trust, and respect. Best of all? You no longer have any worries about what others may think or say. Isn’t that just such a liberating feeling?

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Alan Schin

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