5 Questions Your TS Date Hopes You’ll Ask

Asking questions on a date are a sure-fire way to keep the conversation going, as well as expressing your interest in getting to know her better. Try these out on your next date.

5 Questions to Ask Your Transgender Date

1. What are you looking for in terms of sex?
Your last two dates may have given you the impression that trans women are either perfectly chaste or else, they really get around, and not much in between. Or you may have read or been told that you should never, ever touch a trans woman’s penis, that it’s traumatic for her and must be ignored. You may wonder how to make love to a trans woman without offending and without leaving out anything important.

To complicate things further, some blogs and advocacy material suggest you are never to ask questions about transexual bodies, because it’s always offensive. But I believe that what a woman is looking for and how she likes best to express herself when the time comes is always useful information. Whether you’re dating a cis-gendered woman like myself, or my trans friend Anastasia, there are things you need to know!

Assuming, for example, that Anastasia only wants you to touch her breasts and nothing else, will leave her quite unsatisfied… not to mention upset that you aren’t embracing her as she is. Go for forthright honesty, while avoiding being crass or dismissive. It helps you both if you know what she wants out of her online dating relationships, and how your desires intersect or diverge.

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2. What are some books or movies you love and why?
Exchanging pictures and measurements has its obvious place in dating. But ask her questions about her interests, too.

3. What are your hopes and dreams?
Find a pointed, personal, and sincere way to phrase the question when it comes up naturally in conversation. You’d be amazed how many people reflect back wistfully, “He never asked about my hopes for the world or my unrealized dreams.”

Our imaginations and aspirations are an important part of what we share with our romantic companions, and overlooking or neglecting these aspects is one way to thwart the growth of intimacy between you.

4. What kind of spirituality are you drawn to, or part of?
A trans gal spends as much time on her inside as on her outside. She will appreciate some acknowledgement that her physical body is not the sole defining factor of her identity.

In some cultural and religious traditions, a transgendered person is a uniquely gifted, sacred variant of creation and is considered a shaman, or otherwise ultra-spiritual. Other faith customs have been historically cruel to trans people, but have much more to offer as they become more welcoming today.

You don’t know whether your date’s connections of a cosmic nature are central, nonexistent, or an afterthought until you ask.  If you’re meeting with attractive trans women for hot hookups, you probably don’t need to know her favorite Bible verse or what Hindu goddess she relates to best. But if you’re both looking for a package deal, it’s not just how you play but how you pray that is important.

5. What perfume are you wearing?

After all that, don’t forget the body in your enlightened, holistic pursuit of her mind-body-spirit! Enjoy the sensual details. Remember her favorite fragrances or cosmetics so that you can indulge her down the road. Your thoughtful attention to her scent and other beauty secrets will remind her that you appreciate the little things she does to turn you on.

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