One of the most effective ways to understand Tico culture is to party with them at night or get into the things that they consider as recreations and breaks after a long day at work. Costa Ricans always love to have fun, so you will have to reserve a lot of energy (and money, too) if ever you decide that it's the perfect way to go out tonight.
If what you would like to do is a little bit laid back, i.e. watching people walk by, having a little drink, and catching up with your old friends, then better look for the Parque Central in your city. Most cities and other urban areas typically have this kind of location set up.
Cinemas are fairly famous around these parts and normally feature both local and Hollywood movies, albeit those that come from the latter are dubbed, so you might want to do something about that. Probably that is also another essential lesson you will learn from this night life immersion: learning how to read Spanish to understand the movies that are shown.
If you are into stage plays, there's also an abundance of theatres that can serve you here. San Jose is the best city to be in for these kinds of performances, as a number of theater groups even conduct their plays in English. It is also home to the National Symphony Orchestra, which plays regularly between April and November.
Once the formal recreation is over, it's time for you to show your moves--Costa Rican style! Salsa is fairly popular among these parts, as is soca and merengue. All of these dances are well featured in night clubs all around the city. Meanwhile, the club scene in San Jose can rival those in any big city. All of these clubs feature disco, techno, hard house, reggae, and such.
Meanwhile, in the Nicoya Peninsula, clubs that feature bohemian tastes are also popular.
Clearly, whatever your night life taste is, there's a place for you here!