• Premise of the study: We examined two accounts of the relationship between breeding system and life history variation in a clade of evening primroses (Oenothera, Onagraceae): (1) selection for reproductive assurance should generate an association between self-compatibility and monocarpy and (2) phylogenetic conservatism leads to retention of breeding system and life history traits among closely related taxa. • Methods: We performed over 4000 hand pollinations under greenhouse conditions to determine the compatibility of 10 Oenothera taxa (sections Anogra [17 taxa] and Kleinia [2 taxa)] for which breeding systems had not previously been reported. We used generalized linear mixed models to evaluate the influence of pollination treatment, parents, and population on fruiting success. • Key results: Among the taxa tested, six were self-incompatible, two were variable in compatibility, and two were self-compatible. We combined these data with published studies in Anogra and Kleinia and mapped breeding system and life history onto a published phylogeny. • Conclusions: We found no evidence for phylogenetic conservatism, but detected considerable evolutionary lability in both traits. Additionally, we found no evidence for a consistent relationship between breeding system and life history. Only eight of 19 taxa followed the predicted association between self-incompatibility and polycarpy vs. self-compatibility and monocarpy. Instead, many taxa have retained self-incompatibility, regardless of monocarpy or polycarpy.