Previous research has identified discrepancies between gift givers and receivers in their attitudes towards certain types of gifts, such as self‐improvement gifts. However, it remains unexplored whether there are divergent preferences between givers and receivers regarding probabilistic gifts (i.e., gifts involving probabilistic goods), despite the growing popularity of such goods. To address this gap, we conducted five studies. Study 1 revealed that when presented with a choice between probabilistic gifts and regular gifts, givers were less likely than receivers to select probabilistic gifts. This discrepancy was replicated in two contexts: vertical outcomes of probabilistic gifts (e.g., travel packages with varying prices) in Study 2, and horizontal outcomes of probabilistic gifts (e.g., T‐shirts with different patterns) in Study 3. Study 4 identified that this asymmetrical preference occurred due to different regulatory focus and perceptions of norm violations among individuals when engaging in gift giving. Givers exhibited a higher inclination towards prevention‐focused strategies, whereas receivers displayed a stronger preference for promotion‐focused strategies. Moreover, givers tend to significantly overestimate the extent to which receivers perceive probabilistic gifts as violating gifting norms. These disparities resulted in an asymmetrical preference for probabilistic gifts between givers and receivers. In Study 5, we found that consideration of creativity in gifting moderated the giver‐receiver asymmetrical preference for probabilistic gifts. Specifically, givers with heightened consideration of creativity were more likely to choose probabilistic gifts. These findings imply that gift givers could give greater consideration to probabilistic gifts, and marketers can capitalize on this by promoting probabilistic goods as viable gift options.