5 Tips for Dating Transgender Women

A foundation of trust is the ground level of all meaningful and good relationships—a universal truth to dating that is sometimes forgotten. And it’s easy to forget if you live inside your head and are too afraid to let your ego sit in the back seat and allow your heart do the driving. Genuine conversations, with someone you didn’t really know before, is where you can begin to lay that foundation.

A strong foundation is extra necessary with a trans person, but not much less applicable with a cis woman. Still, it is ONLY RIGHT to treat ALL trans people with the HIGHEST respect and honor because of the bullshit they have to deal with in society, and how their lives are not afforded the same privileges most other people are given. So when dating trans: BE GOOD TO THEM. Whether you’re trans or not!

Be as clear as you can about your understanding of transgenderism. I keep learning new things (and unlearning old things) all the time, and I apply them to my dating life. I had some serious relationship issues when I was having my first forays into gendering and misgendering people, even though I was doing my best to learn. Some people have time for it, some people have space to help you learn, and some people are going to be OUT as soon as you fuck up.

That’s how it goes in the dating world, and you have to remember that when dating someone trans. But if you’re respectful, you will listen and learn from them, and hopefully love too. It’s definitely not impossible to date or have a relationship with a trans person. I’ve done both.

5 Tips for Dating Trans Women

1. Ask Questions Slowly

Take your time in getting to know someone who is trans. Don’t rush in and try to get everything answered in the first date or the first day. That will feel very invasive and probably not help in getting them to trust you to open up.

Give some of your personal information more freely than you might want to—it’s really not as big a sacrifice for MOST cis people to talk about themselves, since society mostly centers on cis bodies. Try to find a nice balance between opening up and letting them open up.

2. Don’t Be Scared

There will be things you may have never known about the reality of trans folks. But don’t let that stop you from letting your body and heart and mind open up to new connections and possibilities in life and love!

You may have never touched a body part that looks like that of the trans woman you are dating, or never known that someone could have their genitals configured the way you are about to discover. So don’t be afraid to learn about the new ways that a human body can exist. There’s never an end to the space our mind or heart can grow.

3. Be Gentle

There are growing pains, and there are learning curves. With trans people, these concepts can be a little more real. But not always. Don’t rush yourself, and don’t rush them into anything. If you want to keep talking and keep learning from each other, take it slow and do so.

There’s no reason to force or pressure anyone into doing things that they aren’t ready for emotionally, socially, or intimately. If it takes ten dates before they are comfortable to lay in a bed together and talk, then take those ten dates. Don’t compare anything to hetero standards in this, as that is what will certainly cause pain. So be gentle, take it slow, and share the truth softly.

4. Let Them Take the Lead

Empowering a trans person to make some decisions they may not normally get to make with people can turn out so delightfully. Everyone has a few things they haven’t gotten to choose or gotten to say on a date, and if you give them the space to trust and allow them to take a leap of faith, hopefully they can ask for something you can provide happily, and let unfold without problem.

For example, let’s say you have always been dominant in bed and are used to spanking your lover, but your trans date asks to spank you—take one for the team and let them! Of course, set your limits and boundaries, but after that… whack whack!

5. Cherish the Memory

You never know what could happen, so make the most of it and live in the moment. Do the best to give it your all and share your truth with them, so you both have the fullest experience possible for as long as possible. I have been with a trans person who after transitioning did not desire me physically anymore, so I had to thank them for the lovely moments we shared together, and watch them find love with someone else.

Take the special moments, and fly away if it doesn’t end up in something beyond a few great dates!

For more tips: Dating Complaints of Trans Women

Enjoy yourself,
Addi Stewart

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