Pro-Environmental Behavior (PEB) plays a crucial role at the individual level in addressing environmental problems. However, it often involves psychological barriers, such as being perceived as “troublesome,” which can prevent action even among those with strong environmental values. This study investigates anticipated emotions—specifically, expectation and regret—as psychological mechanisms to overcome such barriers. By evoking thoughts like “something good might happen if I make an effort” or “I might regret it if I don’t act,” we aim to shift attention from short-term inconvenience to long-term emotional value and thereby promote sustainable PEB. To test this hypothesis, we conducted an experiment where participants completed a writing task designed to evoke anticipated emotions, followed by a behavioral task (PEBT) measuring their tendency to choose environmentally friendly options. The results showed that the combined evocation of expectation and regret increased PEB choices. These findings suggest that anticipated emotions can help individuals overcome perceived inconvenience and highlight the potential of emotional interventions to foster more consistent and sustainable behavior. This study contributes to understanding how small psychological shifts can support meaningful individual action toward sustainability.