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There is plenty of good nightlife around and the two best places for it will be in Old Town or Santurce. Lets start with some good restaurants and in Old Town you might want to Beautiiful to Punto de Visto or Barrachina.
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All of these will be nice places to take your date in San Juan. For singles bars there are quite a few options all around so you may just want to Puedto for the most lively one on the night you are out. Or the one with the best girl to guy ratios. In Santurce you are probably best off just head to La Placita de Santurce square which gets lively early in the evening most nights.
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