Teaquesta,
Welcome to CRT.
You don't give much information about your age, etc. If you're 18-30 years old, you might try the area near the University in San Pedro. I'm going to probably spell this incorrectly, but I believe the street is calle Amargadura. It's very close to long-time favorite music venue, the Jazz Cafe, which is also an okay place to meet locals.
The type of woman you seek will be in the minority. Sadly, classy women with education and English will usually be part of the upper class...which is not to say that some middle-class ladies wion't speak English. I think however, that you'll really need bank, grille and game to rise above the status of gringo whoremonger and start finding real quality gals.
Orange is spot-on. If you don't speak Spanish, start studying. Actually, a local language school which also offers English language courses to ticos might be a good place to get to know some local girls.
If you're really an honest, sincer guy and if you've got a steady income (regardless of level)), you might have more luck in smaller towns, such as Grecia, Palmares or San Isidro del General, but keep in mind that "nice" girls will have to be courted in a way that your parents were familiar with. Slow, sincere and steady. Five or six dates before even a serious kiss. If you've got the patience, more power to you.
Why not grab a box lunch (no jokes here guys, please) and hang out at noon on the Plaza in front of the National Theater, or near the INS building, where numerous secretary types enjoy their lunches.
Finally,, learn to dance "latin:" Salsa, merengue, bachata, cumbia. This culture offers many social opportunities for those who can dance.
Hope this helps.