Starting in fifth grade, CitySquash matches each of our students with an adult in the community who serves as a mentor. The relationship formally lasts up to eight years, until the student graduates from high school, but in practice extends beyond even that. In addition to regular phone and email contact, mentors and mentees spend time together approximately ten times a year and do activities of their choosing. Frequent outings include ice skating, bowling, picnics and visiting museums. CitySquashers who attend boarding school are matched with a second mentor who is an alumnus of her or his high school.