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Adolescent pregnancy remains a major U.S. public health problem. Little is known about pregnancy attitudes in U.S. adolescent males. The study objective was to identify factors from different domains that are associated with sexually active U.S. adolescent males who would be pleased with a female partner pregnancy (hereafter known as pleased with a pregnancy). The National Survey of Family Growth is a nationally representative survey of those 15 to 44 years old. Bivariate and multivariable analyses were performed of the 2002 and 2006-2010 cycles to examine factors associated with being pleased with a pregnancy among sexually active U.S. males. Among the 1,445 sexually active U.S. adolescent males surveyed, 25% would be pleased with a pregnancy. In bivariate analyses, ever being suspended from school, having sporadic health insurance, age, and ever HIV tested were significantly associated with being pleased with a pregnancy. In final multivariable analyses, sporadic insurance was associated with almost triple the odds, and being older and ever HIV tested with double the odds of being pleased with a pregnancy. Higher educational attainment for both adolescent males and adolescent males’ fathers was associated with reduced odds of a being pleased with a pregnancy. One quarter of sexually active U.S. adolescent males would be pleased with a pregnancy. Adolescent males who have been sporadically insured, are older, and ever HIV tested have higher odds of being pleased with a pregnancy. Targeting these adolescent males for more focused pregnancy-prevention counseling may prove useful in reducing adolescent pregnancy rates.