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Performing acts of kindness increases well-being, yet people can be reluctant to ask for help that would enable others’ kindness. We suggest people may be overly reluctant due to miscalibrated expectations about others’ prosocial motivation, underestimating how positively others will feel when asked for help. A pretest identified that interest in asking for help was correlated with expectations of how helpers would feel, but a series of scenarios, recalled experiences, and live interactions among people in the U.S. (n = 2118) indicated that those needing help consistently underestimated others’ willingness to help, underestimated how positively helpers would feel, and overestimated how inconvenienced helpers would feel. These miscalibrated expectations stemmed from underestimating helpers’ prosocial motivation, while overestimating compliance motivation. This research highlights a limitation of construing help-seeking through a lens of compliance by scholars and laypeople alike. Undervaluing prosociality could create a misplaced barrier to asking for help when needed.