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The Dominican Republic can be a bit polarizing to some, and for more than a few reasons. Good and bad. In some ways, I think the Dominican is underrated and somewhat overlooked. Santo Domingo is the capital of the country, and the oldest European city in the Americas. Situated on the coast, you get the beach aspect, the old town feel, and of course a ton of beautiful women that are unlike anywhere else in the world.
First and foremost, the DR is a bit rough around the edges in a lot of ways. Men and women. If you look like you have it, expect to be pestered by people trying to help you out with whatever, and certainly expect some pro and semi-pro women to give you lots of attention, to the point where you literally have to shoo them away. So it goes. Everything is pretty out in the open. Oh, and be direct and upfront. The girls like it here. Take charge. The girls here are unlike any other. And as you may have guessed, knowing Spanish will go a long way.
Make sure you study up before you come, and learn how to be quick with Google Translate. Also, in the DR, other guys are your friends. Try to befriend other guys in bars and clubs, and maybe at the gym, baseball field, or basketball courts. No worries about competition. Lots of good restaurants too. The Colonial Zone Zona Colonial is the historical area of the city. Lots of nightlife. Venezuela Avenue nearby is a good area for a little more seedier bars and clubs as well as sex workers on the streets.
Avoid walking in bad areas at night, and look out for pickpockets in packed areas. The clubs and bars in the DR are pretty wild, and can sometimes feel a bit, well, off. Everyone is there for a good time, and likely on the prowl to take someone home.
Find a girl, dance with her, move on to another to make her jealous, talk to her friends, get a number — the usual. However, this being the DR, the girl may want you to be her sugar daddy, and become your instant girlfriend during your stay.