Cuban people are usually not shy. They are open-minded. In Havana you can find people dressed up in traditional ways to earn money from the tourists for getting photographed. But you can also ask common people for a photograph. Be open and ask for permission. Don’t shoot hidden, from a distance or out of the hip.
Even the Cubans are poor, I was very surprised for not seeing beggars. Cubans want to earn money. They try to sell i.e. cigars, invite to paladars (private restaurants), offering taxi services or making music. Santiago de Cuba was the only town we visited, where some beggars show up and ask for money in an aggressive way. They stuck on my feet while constantly begging.
My travel guide said, every Cuban kid has to learn English at school and stated, one would be able to communicate with the locals. but I definitely recommend learning spanish in case you want to speak with Cubans. Even police officers in Havana don’t speak English. They are helpful and tried hard to understand, but at least it was unsuccessful. Maybe I’d have had more success in getting an answer, if I’d have asked a taxi driver, but I didn’t tried.
Our Cuban guide spoke not only English, he also spoke excellent German and the different local guides also were able to speak a very good German. But the common people don’t speak anything else than Spanish.I know a few words in Spanish and I’m able to recognize Spanish, in case one speaks it. But here I wasn’t able to recognize the language, so I asked our guide, id the Cubans speak another language i.e. a local dialect. On the other hand, I was able to understand a little bit in the TV news. But he answered, that the Cubans don’t have a dialect, but speak extremely quick.
I hope, I wasn’t too quick and you were able to understand me. If not, you have time to read it again and the previous posts on cuba, too.