For the most part, dating someone who is transgender is like dating anybody else. However, if you are cisgender (not transgender) and its your first time dating somebody who is trans, you may want to keep. My guide on how to date transgender women i have discovered that online dating being a transgender woman brings a set of complications that can make dating both difficult and sometimes seemingly frustrating. I answered a question quite similar to this one, but that was more specifically about trans women, so here we go again. A lot of people on here seem very taken with the notion of dating a trans person. the dating scene for transgender women offers a unique set of challenges that cisgender someone whose gender identity matches their biological sex women dont have to deal with. updated date may 21, 2018 how to date a transgender person 5 essential tips for starting a relationship with a trans woman or trans man. Trans date lover provides transgender people a safe online dating community, here you can meet other transgender people looking for love, friendship, relationship and get together. We have millions of transsexuals, shemales, ladyboys, crossdressers, sissies, transvestites, bisexual, bi-curious and straight people registered with us who would love to have a genuine relationship. Yes im a transgender woman, but it doesnt mean the people i date actually respect or treat me like a woman. Maybe they fancy me, but they dont always respect me, and treat me the way i.