Human is a dynamic and complex being that contain not only emotion, but also attachment. Emotion and attachment are progressive which plays an active role in daily life. Adolescence experience expanding social world, a journey to autonomy filled with developmental challenges and adversity such as negative emotional states. Emotional awareness is thought to be an important factor during adolescence to withstand negative interpretation of emotion. Meanwhile, emotional attachment, emotional awareness, and emotion regulation influence life satisfaction and foster healthy relationship that is interlinked with one another. The purpose of this research is to examine the role of emotional attachment, emotional awareness, and emotional regulation in adolescence between the ages of 12 -18 with prior experience of rejection and mild or higher negative emotional states. It is thought that emotional awareness mediates emotional attachment and emotional regulation. Data was measured using IPPA-R, EAQ, and ERQ, which yield a total of 118 participants. CFA and path analysis using LISREL 8.80 were used to analyse the data. Finding indicates that emotional awareness does not mediate emotional attachment and emotional regulation with mother (RMSEA=0.00, Sobel Test=0.63) and father (RMSEA=0.00, Sobel Test=0.46), but mediate emotional attachment and emotional regulation with peers (RMSEA=0.