Singer was born in Philadelphia, Pennsylvania, and was raised Jewish. His father was born Jewish, and his mother converted to Judaism (she herself was born to a Jewish father and a Catholic mother). Singer attended Upper Dublin High School in Fort Washington, Pennsylvania, where he appeared in musicals and was a member of math club, drama club, video club, and chorus. In high school, he was elected class treasurer, wrote for the school newspaper, and played for the school's baseball team. Singer won many awards, including the Upper Dublin Medal, science competition and literary prizes, and was co-winner of the school district's highest award. In his senior year, he was named class valedictorian, a Presidential Scholar and a National Merit Scholar.
Singer graduated magna cum laude from Yale University, with distinction in mathematics and economics. At Yale, he was a member and business manager of both The Whiffenpoofs and The Yale Alley Cats. Three to four months prior to going to graduate school, he worked for Children's Television Workshop (the name, at that time, of the production company for the TV show "Sesame Street",) and then began doing internships. He did an internship for Nickelodeon in New York and an internship for Disney Channel out in L.A., working for Roy Price at Disney TV Animation for four or five weeks. As a result, he developed an interest in script writing. He worked as a business analyst for McKinsey & Company before obtaining a J.D. from Harvard Law School and an MBA from Harvard Business School.
After Singer graduated from Harvard, he was hired by showrunner John Wells to write for The West Wing.

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