Eh! Eh! Another Trini!
Lemme give it to ya straight one brother to another, in general, Taiwanese are EXTREMELY racist. More than you think and more than the responses here would lead you to believe. Think 1950’s USA maybe. You will be stared at. People will say bad things about you to your face. People will freak out and express their displeasure at your presence. The more educated the person, the more potential for racism (you are probably aware of this phenomenon, and it is no less true in Taiwan). The most racist place on the island is Taipei. You will be refused service. With regard to dating, yes, there is a stigma associated with dating a black man and the women can be cold, but all in all Taiwan ain’t all that bad a place for a black man, depending on your attitude. As always, YMMV.
What I came to appreciate about Taiwan is that the people are generally upfront with how they feel about you. They don’t mince words and seem to have little regard for how you might feel about their actions. I don’t think Taiwan has more racists than anywhere else, and it may even have less, but racism will be in your face so you will feel it and see it more. On the other hand, people who aren’t racist will be that much more open to you and they really won’t care. Taiwanese racism is the most apparent in the company of white people because you will see a drastic difference in the way you are treated vs the way they are treated. Occasionally you will be the one treated well while they’re treated like crap! Either way, it is not cool.
Some tips, smile (inwardly too!). Avoid displays of anger. Be patient. The jerks will make themselves known before the saints. Be approachable rather than outgoing. For some reason, the Taiwanese “don’t know how to talk to black people,” as if you were somehow different from any other kind of person. Really stupid yes, but a concern for some people nevertheless. Let them make the first move (they will) and you will be rewarded. Learn some Taiwanese, not just Mandarin. You will be amazed at how much the Taiwanese open up if you use their language rather than the state language. Public face private face and all that.
Oh, but you were concerned about your dating prospects right? You won’t attract as many women as the equivalent white guy would, but by no means will you be a pariah. In fact, your race will act as a kind of filter as the women who will be attracted to you will tend to be more interesting and mature than the average girl. Beware of the static you and your girlfriend will get when you’re out on the town. In some places, being a black man around town is a surefire way to get the attention of at least a C-list celebrity, if you’re with an Asian woman you can crank that up to B-list. Make sure you know a few places where people are used to foreigners to get a breather. In Tapei Tien Mu is a good place to go to feel normal for a while.
BTW, the average Taiwanese can only distinguish between African and African-American, if that. More than a few people thought I was Indian actually. Dey no no nuttin’ 'bout no teensie island but dey’s own!