In this paper, we examine whether variation in reproductive investment affects the health of Roma women using a dataset collected through original anthropological fieldwork among Roma women in Serbia. Data were collected in 2014–2016 in several Roma semi-urban settlements in central Serbia. The sample consisted of 468 Roma women, averaging 44 years of age. We collected demographic data (age, school levels, socioeconomic status), risk behaviors (smoking and alcohol consumption), marital status, and reproductive history variables (the timing of reproduction, the intensity of reproduction, reproductive effort and investment after birth), in addition to self-reported health, height, and weight. Data analyses showed that somatic, short-term costs of reproduction were revealed in this population, while evolutionary, long-term costs were unobservable—contrariwise, Roma women in poor health contributed more to the gene pool of the next generation than their healthy counterparts. Our findings appear to be consistent with simple trade-off models that suggest inverse relationships between reproductive effort and health. Thus, personal sacrifice—poor health as an outcome—seems crucial for greater reproductive success.