Crossdresser Dating: How To Date LGBTQ Individuals

August 18, 2019

When it comes to dating transgenders, many people are at a loss of what to do. Read more about transgenders in this link. They might come off as too awkward, especially if it is their first time dating a lesbian or a transwoman. When you are one of them and you have found someone to date, you might want to do a little research before meeting her or him.

The first thing that you need to think about is the reason why you are dating them. If you are just curious about what it feels like, you may have the wrong reasons. Transwomen and lesbians are people who have feelings too. They want long-lasting relationships. Although, some of them may be looking for one night stands, there are still some who seek true love. They welcome someone who respects and understands them on a deeper level.

Here are some Tips to Start With

1. Pick Somewhere Comfortable

You might want to meet at a shopping center or a park, which is a convenient location for both of you. Before the date, you can go on your browser and check if there is an all-gender restroom near the meeting place. This will prevent awkwardness when both of you decide to go to a restroom. Ask your date about his or her favorite food and go to that restaurant. Do not complicate and overthink everything. As long as both of you are comfortable, then enjoy yourselves in the process of getting to know each other.

2. Date Someone That You Are Comfortable With

If you are someone who is flamboyant and everyone in your family knows about your gender preference, then date someone who is also open. This will prevent secrecy and needs of privacy later on. If you date someone who has not come out yet, respect them. However, when you are open and they are close, there could be tension down the road. Other people are straight and they are dating a transwoman. Dating one will not make them less of a man. If you are looking for other information about dating trans, this is the best resource for finding a new partner that is transgender and will help you be more of a man. They will prove to you that dating them has nothing to do with your sexuality.

3. Always Offer To Pay

When you are dating a transwoman, she would appreciate it a lot if you will offer to pay for the delicious lobster and crabs that you both just ate. This will show that you are sincere and money is not the only thing that motivates you to be with them. When the bill is delivered, you might show her that you are willing to pay by pulling out your card or your cash immediately. The best ones may even offer to split the bill in half, but the others will appreciate it if you make them see that you can take care of the bill for the first date.

4. No Exes Should Be Involved

There are LGBTQ communities that are tightly knit. This means that if you have dated a crossdresser before, there is a chance that he or she might be an acquaintance of the one that you are dating with at the moment. You never know the mutual friends you have with your date. Knowing this, do not discuss exes in the first place. If she asks if whether it is your first time dating someone from the LGBTQ, just answer with a simple yes or no. Discussing your ex might open a can of worms that you should have never touched in the first place.

5. Do Not Add Your Date On Social Media

This does not apply to those people who have found their dates on Facebook, Twitter, Instagram, or other social media platforms. More information about social media platforms can be found here: This is for the people who have found a match on dating sites. It is tempting to add your date on Facebook before meeting them so that you can stalk their profile. However, if the whole meet and greet event did not go well, you will be stuck with someone whom you do not want to be around. It will be awkward unfriending them as well. Besides, you will also not want your profile getting tagged in the Facebook community as someone who sucks in dating if something went wrong.

Split Advice

If you and your date find each other interesting and you are ready to take the next step, then take it slow. Even if you are living in an expensive city and it will make financial sense to live together, there are still boundaries that you need to establish.

For Women

If you are dating a lesbian, give each other space. Do not spend every single night on his place. There are times when you both needed some time alone to sort things through. Do not hire a U-haul and move house with him in the early months that you are dating as it can become a disaster.

If you are unsure of your feelings and both of you are still struggling to trust each other, expect that there will be late-night fighting, early morning yelling, and flying plates. Establish a strong foundation before moving in. By that time, both of you are sure of each other’s feelings. You both know that you have each other’s backs regardless of what other people will say.

For Men

If you are dating a transwoman, put a label on your relationship. Call your transwoman your girlfriend if that is the truth. If you are bisexual and you want an open relationship, then say it at the beginning. Be honest about your feelings. Tell them early on whether you are looking for a long-term relationship or just a quick roll on the hay.

A Final Word

Here are just some of the tips that you need to follow when dating a crossdresser. Not all tips will apply to you and your date. Everything will still depend on the person you are with. If he or she is the type to pick somewhere more private, then let her. Keep things slow. Do not talk about marriages or love on the first date. Get to know your date and see her or him as you would with any other man or woman. Lastly, do not forget to enjoy! If you want to show your support for the LGBTQ+ community, you can easily shop for LGBTQ flags at this store and choose from a wide variety of high-quality flags and banners representing different identities, all available for purchase online in the UK.

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Andi Perullo de Ledesma

I am Andi Perullo de Ledesma, a Chinese Medicine Doctor and Travel Photojournalist in Charlotte, NC. I am also wife to Lucas and mother to Joaquín. Follow us as we explore life and the world one beautiful adventure at a time.

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