Options for Youth’s (OFY) mission is to expand the opportunities available to vulnerable Chicago youth by developing programs that build upon the strengths and maximize the potential of each young person. The organization works with teenagers and children who are growing up and going to school in some of the most underserved neighborhoods in Chicago. Through three intense programs, OFY works with participants to overcome significant challenges, finish high school, and become productive members of their communities. The Subsequent Pregnancy Program helps first-time teen mothers graduate from high school and become self-sufficient before deciding to have another child. Our program is one of the few in the country that focuses on delaying a second pregnancy, therefore ensuring a greater chance of graduating high school. Among the 5,000+ adolescent mothers who have participated in SPP, 97% delayed a second pregnancy and 95% graduated high school. The What’s Up with Manhood program empowers teen boys to make healthy lifestyle choices, challenge gender stereotypes, build healthy relationships with others, and become peer advocates for male health. Of the 300+ young minority boys who have participated in the program, 99% graduated from high school and a majority have gone on to college. The Options Program is a high school-based initiative that drives high school graduation of parenting students (both mothers and fathers) and ensures school readiness for their babies and children. By ensuring that each young person in one of our programs graduates from high school, has access to post-secondary education, and has the personal ongoing support needed for success, we are helping young men and women break out of the cycle of intergenerational poverty.