We examine whether changes in U.S. pregnancy, birth, and abortion rates between 2009 and 2015 reflect underlying change in the incidence of pregnancies classified by retrospectively reported pregnancy desires: pregnancies reported as having occurred at about the right time, later than wanted, too soon, or not wanted at all, and those for which individuals expressed other feelings, including uncertainty, ambivalence, or indifference. We calculate the proportionate distributions of these pregnancies and rates among U.S. women aged 15–44, as well as change over time, overall and among age groups. Characterization of desires for a past pregnancy shifted in a number of ways between 2009 and 2015, and changes across age groups were not uniform. Rates of pregnancies reported as occurring later than wanted increased among older women, while rates of pregnancies reported as occurring too soon decreased among all women. These findings shed light on previous research documenting an increasing age at first birth, increasing rates of pregnancy and childbearing among the oldest age groups, and changes in patterns of contraceptive use, particularly among young women. Our analysis explores limitations and challenges of two major sources of data on pregnancies in the United States and their measures of retrospectively reported pregnancy desires.