The SouthCoast Mentoring Initiative for Learning, Education and Service, Inc. (SMILES) is a school-based one-to-one mentoring program in New Bedford and Fall River that was created to address the pervasive and chronic dropout rate in the region. In the two SouthCoast cities, more than 700 students drop out of school each year. While many view the dropout problem as an education issue to be addressed by school departments, SMILES views it as a social issue requiring a large-scale comprehensive response from the community in partnership with the schools. SMILES enjoys a strong working relationship with both the New Bedford and Fall River public school systems. We currently support over 600 mentoring matches in 30 programs hosted by 19 different schools within New Bedford and Fall River combined. Our five year plan is to dramatically grow the organization, by the school year 2012-13, to matching 3,000 mentors with students identified as showing characteristics of becoming a school drop-out by school administrators counseling and guidance staff. The youth identified for our program have displayed one or more of the following characteristics as evaluated by school staff: poor school performance, poor attendance, challenging family situation, school discipline issues and overall self-esteem. Our mentoring programs meet for one hour each week; same day, time and place within the school building. Matched mentors and mentees meet with other pairs at the school where a SMILES program facilitator leads one-to-one and group activities to help the matches build healthy relationships.