Your first time dating a transgender woman

Whether you’re a cisgender woman or one of many cis men who have always wanted to try transgender dating, your first time signing up for online dating or going out on a trans date can feel daunting. Fortunately for you, with the right approach it can be a great experience.

You don’t need to overthink it when dating trans people, be it for hookups or serious relationships: transgender women and men are just like any of your other dates. They’re looking for the same kind of experiences and opportunities you are. 

In this article, we’ll cover some of the basics you should know before your first date with a trans person, and what you should avoid as you date in the LGBTQ community. We’ll also give you some pointers on how to make sure your date is a success. 

What you should know before a first date with a transgender woman

Online dating within the LGBTQ community is an exciting experience, and can be rewarding for many straight guys and women who are progressive with their interests. However, there can be a few terms and ideas to keep in mind if you are new to dating non-cis singles. 

Here are some key terms, things to remember, and general advice to know before your first date with someone trans: 

  • Trans girls and trans women are women who were born as another sex but identify their gender as female. This means that they put on clothing and make-up to appear feminine, and may even take HRT or have surgical operations to further their transitioning. 
  • Pre-op and post-op are terms that refer to before and after gender reassignment surgery, with pre-op being someone who is planning on getting the surgery but has not yet, and post-op being someone who has had the surgery to change their breasts and / or genitals already.
  • MTF is an acronym for “male to female”, and refers to a man who has transitioned to becoming a woman. FTM is “female to male” and refers to a woman who has transitioned to becoming a man. This doesn’t always require surgery, and can depend on an individual’s goal for themselves. 
  • Some people can question their sexual orientation as they start to trans date. This can mean a “straight man” thinking they’ve suddenly become a gay man, or ciswomen wondering if they are lesbians. The truth is that there’s no hardline for what your sexual orientation has to be or is when you start trans dating, and you are free to be attracted to whomever you are attracted to. If straight guys find themselves attracted to a trans woman, it’s because she is a woman and that’s enough for them.
  • Most online dating apps and websites are evolving to include options for trans dating, whether it is for hookups or a long-term relationship. While there are exclusive services you can use to meet a trans date, they aren’t by any stretch your only options.
  • With that in mind, you may find that many trans singles can be apprehensive about using dating services for one reason or another. This can include bigotry that dehumanizes them, to meeting people who have a transamory fetish and aren’t interested in them as such.
  • Don’t treat your trans date as the be-all, end-all representation of LGBTQ identities and information. Every person has their own journey and goal, and so they can only speak about themselves. 

Vector art of transgender couple together

Why “Shemale” is a common term in online trans dating

If there’s a term many transgender people dislike and have to contend with, it’s “Shemale”. Unfortunately, many people are more familiar with this term than others thanks to how prolific its use in the porn industry and then the casual dating industry thanks to its use in porn.

Many men are introduced to the idea of casual sex with a trans person through pornography, and so adopt the lingo as they approach actual transsexual people. It unfortunately leads to awkward situations and expectations that aren’t realistic. 

“Shemales” as such don’t exist outside of pornography, and this is largely because of what a shemale actually is. In a nutshell, they are sexual objects created to fulfill the fantasy of people looking to fill a niche fetish or kink. There’s nothing real about these portrayals.

Other terms which are frowned on by the LGBTQ community that often come up in porn or on dating services include “tranny”, “ladyboy”, and “tgirl”. Avoid using these to address someone who is trans, and if you aren’t sure how to refer to someone, ask them first. 

Better yet, simply use their name. 

How to avoid microaggressions and other no-goes on your first date with a trans woman

Microaggressions, especially against trans people, can seem like simply banal actions or things you say that you’d take for granted normally. However, because of a person’s own trauma or struggles, it brings up painful or difficult feelings. 

To be more clear, microaggressions are indirect, subtle, or unintentional instances of discrimination against members of a marginalized group, in this case trans persons.

This can be deadnaming someone, which is when you use a prior name they had before transitioning, or refusing to acknowledge their pronouns of choice. It can also be backhanded compliments like “you look pretty for someone trans” or “maybe try shaving a bit better”. 

The rule of thumb you should generally follow is to treat them with the respect and dignity that they deserve. Ask them what they would like to be called, don’t walk on eggshells around them, and be courteous to them. Treat them like any other date. 

Vector art of transgender couple together

How to make your date with a transgender woman a success

If you are looking for the best dating experience with someone who is trans, you really need to focus on treating them first and foremost as a real person. Respect their boundaries and preferences, and make an effort to show them a nice time. 

Depending on the dating site you use, or however you meet her, make sure she understands why you are interested in her. Focus on her as a person rather than something base or degrading. 

Don’t be shy on taking your date out either, whether it is for dinner and drinks, or even to the club. You can also go for walks in the park, see a movie, all the usual dating things you would do with someone who isn’t trans. 

Really, if you want your date to be successful, treat them as a person you’re actually interested in being with. That alone will go a long way for you. 

After the first date with a transgender woman: Where to go from here? 

Assuming your first date with a trans man or woman goes well, you might be asking yourself when to text and, if you thought it went really well, when you can be intimate. Of course, you don’t want to rush anything with your date, but you don’t want to come off uninterested.

When it comes to texting transsexual women or men, the general rules apply for any other date. If you both thought it went well, there’s no reason you can’t send a message the next day saying how much you enjoyed the date and would like to meet again. 

Intimacy is a different matter though, and the old rule of thumb was at least three dates. However, this is something that truly depends on your comfort and hers, so be open about your interest and start a conversation about how and when you two could enjoy sex.

Respect her decision if she wants to wait, or isn’t quite there yet with you. If you two are really a compatible match, it will happen in due time. 

Vector art of transgender couple together

FAQ about your first time dating someone trans

Dating someone who is trans for the first time is a big thing for someone new to the LGBTQ community. However, that doesn’t mean that your experiences are going to be out of the ordinary. Really, dating a trans person is similar to dating anyone else who is CIS or other.

Nevertheless, we’ve answered some of the most frequently asked questions about dating someone who is trans for the first time to help you get started. 

Am I gay if I decide to date a trans woman? 

No, unless you want to consider yourself as gay. If your date is identifying as a woman and you want to make an effort to be with her, then there’s no reason to identify yourself as a gay man if you want to try and validate her identity as a woman. 

If you do feel as if you are gay for being with a trans woman, then there’s nothing wrong with that either. Embrace who you are, whatever makes you most comfortable. 

How can I introduce my friends and family to my trans date?

Talk it over with your trans date first and make sure they are comfortable and okay with meeting your family and friends. If they are, then speak to them and ask if they would like to get to know her. As long as everyone is willing to try, there’s no reason not to introduce them.

Of course, if you get the impression that it wouldn’t go well or could be stressful, then hold off on introductions until you can assure that it will go well. Make your date’s mental and emotional health a priority here, if you are serious about the relationship. 

Is there a difference between cross-dressers and trans people?

Yes. “Cross-dressing” is more of an action or behavior, and does not say anything about the person’s motives for why they are doing that. Someone who isn’t trans could cross-dress, for example. They might not see themselves as a woman, and may just enjoy the clothing. 

In short, just because someone cross-dresses does not mean they are transgender.