If you’re new to dating transwomen, the idea of dating a woman that is high maintenance can be daunting. Transwomen have certain things that they struggle with that cisgender women might not, and it can take some extra patience to help them with the things they’re dealing with. Don’t worry, we’ve created a guide to help you navigate this new territory and to help you be the best partner you can be.

Learn to Recognize Triggers Transwomen May Struggle With

Being a transwoman is not easy and there are some things she will experience that might trigger her and will be difficult for her to deal with. Learn to recognize the things that bother her and find ways to help her through it. For example, if she gets misgendered, this may cause her to feel upset that she was not identified properly. You may need to take a moment to reinforce that you think she is beautiful and help to reaffirm her gender. Taking the time to recognize things that can hurt your partner and finding ways to help her deal with them will help your relationship to blossom and you can start being the best partner you can be.

Discuss Your Expectations With Your Partner

If you’re dating a high maintenance transgender woman, you may be a bit overwhelmed at first with some of the things she may expect from you. If you feel uncomfortable with any of these expectations, instead of internalizing these frustrations, set aside some time to talk about it with her. Raise any concerns you have early on so you can talk them through and discuss how you should handle them. You should also make sure you discuss any expectations you have from her as well. This is also a great time to talk about any boundaries either of you want to set to make sure you’re both on the same page and can maintain open communication.

Don’t Forget About Your Own Needs

When you’re dating a high maintenance trans woman, it can be difficult to remember to take care of yourself. Make sure that you create space for yourself to meet your own needs! Whether you set aside some time to work out, meditate, or just keep up with hobbies that you enjoy, don’t forget that you also have needs and need to take care of yourself. Taking the time to rest, recharge, and focus on yourself allows you to clear your head and really be there for your partner.

Set Goals Together In Your Relationship

Being supportive of a high maintenance transgender woman can be difficult if you feel like you’re the only one trying to help her. A good way to make you both feel appreciated is to set goals together. By working as a team to reach a common goal, you can begin to build shared experiences and this can give you activities to do together and can help both of you feel productive and fulfilled. You can start with something small like cooking a meal together and work up to something larger such as saving for a vacation you want to take. By uniting under a common goal, both of you will have something to work towards and can start to feel accomplished together as a couple.

Educate Yourself About Transgender Issues


If this is your first time TS dating, there may be a lot of things that are new for you and that’s okay! If your partner says words that you don’t recognize, take note of them and either ask your partner to explain what they mean or take a few minutes to google it. There are things your partner will go through that you may never empathize with, but you can certainly learn to sympathize with her and do your best to understand her struggles. Never be afraid to ask about things you don’t understand, and of course you can do research on your own as well. Educating yourself will show her that you genuinely care about what she experiences and will bring you closer as a couple.

Seek Professional Help If You Need To

There is nothing wrong with admitting that you need help, and even if there’s nothing wrong, therapy can still be a wonderful experience. If you just want to vent to someone or feel like you need some advice from an unbiased source, therapy can be a great option for you. You may also consider couples therapy if you and your partner thing it may be productive for you as this can help you work through any issues you may have. Of course, there doesn’t need to be anything wrong for you to go to therapy, it can be a healthy way to make sure that you take care of yourself and your mental health. And when you are at your best, you can truly give your best to your partner.

Find People Who Understand What Dating A Transwoman Is Like

Transgender women make up a small part of the population, and many people will never understand what its like to date a transwomen. This can lead you to feel isolated and maybe feel like no one understands. Here at MyTransgenderCupid, you can find many like-minded people who understand exactly what you’re going through. This is more than just another TS dating app; it is specifically designed to bring together transgender women and decent men. On our site you will also find many helpful Transgender blogs resources that help you feel less alone and even give you some ideas for fixing issues you might not know how to resolve. And of course, if you have any friends that are transwomen looking for men, or vice versa, feel free to recommend our site to them!


Dating A High Maintenance Transwoman Wrap Up

Today, we discussed some of the struggles that men may face when dating a transgender woman. We gave you some tips to help you navigate this new territory and help you be the best partner you can be. We also answered some FAQs you might have to help save you some time! If you are struggling with dating a transwoman, we hope you found this article helpful and beneficial to your situation. For more resources and information, check out MyTransgenderCupid.

Dating Transgender Women FAQs

Dating transwomen can be difficult, especially if it is your first time. We understand that you may have questions, but you might not know who to ask. Don’t worry, we’ve got your back. We have compiled some frequently asked questions that you may have and answered them for you.

Transgender women face many issues in their life that other people may not be familiar with. Many transgender women have difficult relationships with their family due to coming out as transgender. They may struggle with things like gender dysphoria (feeling like your body does not match the gender you identify with) which can have negative impacts on their mental health. Transgender individuals may also face extreme discrimination in their daily life that many people never face. They may not feel welcome in common women’s spaces such as bathrooms and locker rooms. Transgender women are much more likely to be the victim of violent crimes which can lead them to have to take extreme measures to protect their safety.

These are just some of the issues that transgender women face, and there are far more than we can fit into one article. Be sympathetic to issues that transgender women face and always be willing to listen to their struggles and try to understand what they’re going through.

Many people are getting serious about there mental health and due to this rise in popularity as well as advances in technology, finding professional help is easier now than ever. Check out online therapy resources that allow you to connect with a therapist from the comfort of your home. Many apps allow you to choose a LGBTQ therapist or someone who understands these issues, and this may help to connect you with someone who is familiar with the struggles of queer individuals. If you need immediate assistance, you can call emergency services in your area (911 or 988 for the United States, etc). You can also reach out to local queer centers or support groups to help you meet people that understand these struggles.


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.