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Low self-esteem is often related to interpersonal difficulties. In fact, low self-esteem people fear rejection and tend to adopt self-protection goals. In the present work, we tested the idea that when low self-esteem individuals decide to sacrifice personal preferences for their relationship, they come to regret those actions, with further consequences for their well-being. We conducted a study with 130 couples, using experience sampling, daily diary, and a 1-year follow-up assessment. Results showed that low self-esteem is related to greater regret of past sacrifices, which, in turn, affects negative mood, stress, and life satisfaction. Furthermore, mediation analyses revealed that low self-esteem individuals feel less supported by the partner after they sacrifice, which helps explaining why they come to regret their sacrifices.