Those seeking help systematically underestimate the likelihood that strangers will help them (Bohns, 2016). However, it is not known whether this same error persists when requesting help from people with whom we interact regularly. In three experiments (the last of which was pre-registered), participants (N = 310) predicted the likelihood that either their friends or strangers would agree to a request for help. Participants then approached members of one of these two groups (i.e., friends or strangers) with this request (N = 953). We confirmed our predictions that (1) overall help-seekers would underestimate the likelihood that those they approached for help would agree to their requests and that (2) this underestimation error would be smaller for participants making requests of friends. We also found that (3) the underestimation effect persists even for those making requests of friends and (4) help-seekers expected the rate of helping between the two groups to vary more than it did. We discuss and test several mechanisms that might account for these effects. These findings suggest people may over-rely on their friends, and discount the role of strangers, when seeking help.