It’s not hard to meet – or date – a trans person in Singapore. Singaporean ladyboys are open and friendly by all accounts. Please note that shemales in Singapore, as elsewhere, is a derogatory term the trans community does not embrace.
That said, your first date could be to a dance show, a cabaret show, or in one of the many trans-friendly clubs, bars, or theaters.
Before or when you start dating a trans person, you might have problems with your perception of your sexual orientation. Research has shown that people tend to make judgments about sexual orientation based on limited information, such as voice, face, or behavioral display. Traits that are untypical for a gender serve as cues – wrongly – to sexual orientation. For example, some people can tell a person is trans by their voice or their gait. They will automatically assume a trans woman likes men or a trans man likes women.
At any rate, know that no sexual practice is owed by or defines a sexual orientation. What do we mean by this? For instance, you can’t say only lesbians do oral, only straight people do vaginal, and only gay men have anal sex. Sexual intercourse with a person does not and should not change how you identify yourself and your partner.
In Singapore, most trans women arrange dates after meeting someone online. Know what you are looking for in a potential partner to make this process easier. For example, are you looking just to hook up or for something more? Do you have any preferences in terms of surgical status: pre-op, post-op, or non-op? Resistance or unwillingness to clarify your preferences could make your partner feel undesirable or invisible.
A lot of trans people in Singapore are still classified in the wrong gender despite having undergone surgery, which is quite expensive in this already expensive enough city-state. It is exhausting for a trans person to keep having to correct people and deal with being mis-gendered. Be as open about your attraction, wants, and needs as you can to avoid reinforcing transphobia.