This research examines the differing evaluations of “gifts with choices”—gifts allowing recipients to select specific attributes—by givers and recipients. Through multiple studies, we find that recipients view such gifts as less thoughtful, resulting in reduced appreciation. Conversely, givers underestimate the negative impact of offering choices on recipients' perceptions. This giver–recipient asymmetry stems from recipients associating these gifts with less effort from the giver. Importantly, the discrepancy diminishes in socially distant relationships or when givers provide information about their preselected gift attributes. This study expands gift‐giving literature by being the first to investigate gifts with choices, unveiling a unique giver–recipient disagreement, and exploring its underlying causes and boundary conditions.