We posit that when help-seekers ask for assistance, they may not ask as quickly as helpers would like. We first demonstrate this discrepancy in two field studies (Studies 1 and 2) involving manager-subordinate and teaching assistant-student relationships. Then, in a tightly controlled experiment (Study 3), we replicate the effect and identify two parallel mechanisms: help-seekers focus more on feeling less discomfort (thus wanting to ask later), whereas helpers focus more on feeling more useful (thus wanting to be asked sooner). Lastly, we developed and tested an intervention based on reducing help-seekers’ underestimates of how useful helpers want to feel (Study 4). Although the intervention did not reduce the discrepancy between when help-seekers ask for help and when helpers want to be asked for help, moderated mediation analysis provided causal support for the mechanism—reducing help-seekers underestimates of how useful helpers want to feel indirectly reduced the discrepancy in when they asked for help vs. when helpers wanted to be asked for help.