Analyses of lifetime fitness in birds are typically based on estimates of breeding success, in particular the number of offspring fledged. Small and isolated bird populations often have a male-skewed adult sex ratio, so that male lifetime productivity depends to a large degree on pairing success, but few studies have focused on patterns of lifetime pairing success. The Norwegian population of Ortolan Buntings Emberiza hortulana is strongly male-skewed, such that in any year about half of all males are unpaired. Pairing success of first-year males (16–44%) was significantly lower than for older males (52–89%). Lifetime pairing success was correlated with lifespan and was strongly skewed, with a majority of males being paired only once or never, and only 11% paired three or more times despite a stable lifetime annual survival rate of 63%. Males that were paired in one year were more likely to be paired the next year than males that were unpaired in the previous year. The shortage of females caused even the older males to have a substantial probability of becoming unpaired, and 49% of long-lived males (known as adults for at least 4 years) were unpaired after years in which they were paired. Pairing success in the Ortolan Bunting therefore follows similar age-related and lifetime patterns in breeding success documented in other species. However, even the older males ran a high risk of not being paired, contrasting with earlier distinctions between pre-breeding and breeding lifespans. I discuss the importance of knowledge of pairing success for the management of endangered and declining populations.