The present study is a first attempt to link self-reported difficulties in everyday emotion regulation (ER) with evaluative conditioning (EC). We conducted a within-subject study in which participants (n = 90) filled the Difficulties in Emotion Regulation Scale (DERS) and were exposed to neutral conditioned stimulus (CS) paired with mildly or highly arousing negative unconditioned stimuli (USs) and positive USs. Participants then filled a contingency awareness measure. Results showed (i) that CSs paired with highly arousing negative USs were more negatively evaluated, (ii) that the EC effect with highly and mildly arousing negative USs was stronger among participants with greater self-reported difficulties in everyday ER. Moreover, participants were more likely to be aware of the CS-US contingencies with highly (vs. mildly) arousing negative USs. Implications for the understanding of maladaptive behaviors and for future directions in EC research are discussed.