People's relationship with social media and their contacts on them can be problematic. People may engage in social media in a compulsive and hasty style to increase their popularity, reputation and enhance their self-esteem. However, this problematic attachment to social media may result in side effects on people's well-being. Therefore, people may need assistance to reform their relationship with social media in a way that it maintains different aspects of their online interaction, such as empathy with others and maintaining their popularity and relatedness. In order to provide the tools and methods to support people in reforming their relationship with social media, towards a healthier usage style, we need to understand the experience of people who suffer a problematic relationship with them. Most studies on the topic are based on methods which would lack ecological validity, e.g. using surveys and interviews, and do not capture or imitate such a digital experience as lived. In an attempt to better explore how people experience problematic attachment and relationship with social media, and their associated emotions, we conducted a multistage qualitative method study including a diary study to gather lived experience. We aim to inform both users and designers towards a managed and tool-supported reform of their problematic relationship with social media and, ultimately, having a healthier online interaction.