Working with high school students can be a challenge, especially if we're meeting to help them bring up low grades. One thing I do when I meet the student for the very first time is to ask them questions about their interests, like sports, school subjects, music and movies. In the math problems that I create, I incorporate references to these interests.
For example, a question may be to find out how many points they need to score in a basketball game to win or feature their favorite celebrity buying too many groceries. It gets their attention and makes them laugh, helping me build a good rapport with them and keep them interested in the material