First, the answer of this question is definitely NO. Dating a transgender woman will never make you gay.What's the different between gay dating and transgender dating?
Transgender dating means transgender people dating non-transgender people or transgender people. Transgender women are real women, transgender men are real women, so dating transgender women never mean you are gay, dating transgender men never mean you are lesbian.
Gay dating means people of the same gender dating with each other, this is totally different from transgender dating. I cannot understand why some people misunderstanding gay dating and transgender dating. They are completely different from each other.