Being overweight or obese is if often associated with prejudice, stereotyping, stigmatisation, and discrimination, and can lead to both physical and mental health difficulties. It is commonly thought that weight loss will lead to improvements in various areas within the individual’s life including; body image, social, family, and work. The present study aimed to enhance the understanding of the weight loss journey and the associated outcomes, with a specific focus on the expectation that individuals held, and how these compared to actual outcomes and perceptions. Semi-structured interviews were conducted with eleven participants. Data was then analysed using a grounded theory approach. Findings showed that although weight loss had benefits such as fitting ‘normal’ sized clothes, increased attention, and a growth in confidence, there were also difficulties that were experienced. These included: a lack of support and unintentional sabotage, perceived body imperfections, and time taken for body perception to match up with actual physical appearance. It was found that positive outcomes of weight loss (such as compliments) could actually be viewed from a negative perspective and may have the opposite effect than what was intended. While some outcomes were congruent with participants’ expectations, there were also instances where these were incongruent; for example being left with loose skin as a result of weight loss. It appeared as though having an expectation of life being ‘perfect’ after weight loss was more likely to lead to dissatisfaction, while having some form of education or insight about what life and their physical appearance would be like was more likely to result in higher levels of satisfaction.