Three experiments investigated individuals’ preferences and affective reactions to negative life experiences. Participants had a more intense negative affective reaction when they were exposed to a highly negative life experience than when they were exposed to two negative events: a highly negative and a mildly negative life event. Participants also chose the situation containing two versus one negative event. Thus, “more negative events were better” when the events had different affective intensities. When participants were exposed to events having similar affective intensities, however, two negative events produced a more intense negative affective reaction. In addition, participants chose the situation having one versus two negative life experiences. Thus, “more negative events were worse” when the events had similar affective intensities. These results are consistent with an averaging/summation (A/S) model and delineate situations when “more” negative life events are “better” and when “more” negative life events are “worse.” Results also ruled out several alternative interpretations including the peak-end rule and mental accounting interpretations.