Dating a genderqueer person
Now for some definitions of the terminology involved: Portrayals of trans people range between Acceptable Targets and Once Acceptable Targets.
While many portrayals are sympathetic, many are also built around jokes about the character "really" being another gender — plus, bigoted and inaccurate "trans panic" jokes portraying trans people as deceptive cross-dressers ("Oh no, the hot chick is really a man! Because this line of reasoning is often a motive for murder in Real Life, this type of humor goes beyond mere Unfortunate Implications.
Stereotypes and caricatures of trans women in the media can range from heavily masculine-bodied people wearing unflattering budget dresses and wigs, to highly attractive and feminine women whom men fear.
In live action movies, trans people are almost always played by either a cis man or a cis woman, as opposed to a actual trans actors, which doesn't exactly do wonders for visibility.
In the 21st century, the related concept of a "glass closet" emerged in LGBT discourse.
This term describes public figures, such as entertainers or politicians, who are out of the closet in their personal lives and do not engage in the tactics (such as entering a lavender marriage or publicly dating a person of the opposite sex as a "beard") that were historically used by closeted celebrities to disguise their sexual identity, but have not formally disclosed their sexual orientation on the public record — and who, thus, are technically neither fully in the closet nor fully out of it.
Transgender people (trans for short) are those whose gender, meaning their innate mental blueprint of how male or female they are, doesn't match their physical looks and/or the gender they were assigned at birth.