I have a student who is 14 years old and many of his social interactions are like that of a 8 year old. For example, when playing a game, he constantly tells the other player when to go. Usually before he has even finished his move. Also, he likes to "sneak" up on people to "scare" them. What is the best way to teach a student the appropriate social skills? We have tried role playing and it doesn't seem to be helping./
Never underestimate the power of peer modeling! You may want to try getting the student in a social skills group with students who have appropriate social skills. Peer pressure to perform appropriate social skills can be a very powerful tool.
Keep using role-play and make the situations meaningful for the student.
You may also want to consider using videos that show both appropriate and inappropriate social skill use. Then have the student analyze the vidoe... identifying what made the behavior appropriate or inappropriate.