The job search literature addresses characteristics that facilitate reemployment but does not address the management of employment gaps. Building upon prior job search research, we suggest that facilitation-based emotional intelligence reduces employment gaps through self-esteem. Further, understanding-based emotional intelligence moderates the negative relationship between employment gaps and subsequent employment fit. We test these hypotheses employing a multi-wave data collection of 157 workers. At Time 1, undergraduate students completed a measure of self-esteem and a test of facilitation- and understanding-based emotional intelligence using the MSCEIT© V2.0. Ten years later (Time 2), the same individuals reported their employment gaps, person-organization fit, and person-job fit. Findings suggest that facilitation-based emotional intelligence is associated with higher self-esteem, which in turn leads to reduced employment gaps. Additionally, understanding-based emotional intelligence moderates the relationship between employment gaps and person-job fit such that low understanding-based emotional intelligence enhances the negative relationship and high understanding-based emotional intelligence neutralizes the relationship. This study contributes to the emotional intelligence, career management, and job search literatures by illustrating that emotional intelligence plays a role in preventing employment gaps and managing the difficulties associated with subsequent reemployment.