We evaluated age differences in the relationship between judgments of learning (JOLs) and the choice to restudy a subset of items under two conditions: 1) when a retrieval attempt was explicitly prompted during monitoring; 2) when a retrieval attempt was not explicitly prompted. Young and older adults studied unrelated word pairs. Item-by-item cue-only judgments followed, where participants either attempted to recall the target before providing a JOL or only provided a JOL. After the monitoring phase, participants reported how many total items they wanted to restudy. However, during the selection phase, participants selected half of the presented items to restudy. After restudying selected items, participants received a final cued recall test. Requiring individuals to attempt retrieval increased monitoring reaction times (RT) and decreased JOL magnitude, but did not affect self-regulated learning. For both monitoring groups, individuals were more likely to select items they rated with lower JOLs and items that they spent more time monitoring (i.e., greater RTs). In addition, older adults demonstrated a weaker negative relationship between JOLs and restudy selections, but no difference in the relationship between RTs and restudy selections, compared to young adults. Older adults also indicated wanting to restudy more total items than younger adults. Explicitly prompting retrieval during monitoring did not impact these observed age effects, or interestingly, final test performance. Overall, the results of this study suggest that prompting explicit retrieval prior to monitoring may have little direct effect on self-regulated learning or final test performance.