Food has become a significant lifestyle and life quality generator, and consumers are increasingly developing food regimes with expectations of healthier, happier selves. The global food industry has turned to delivering towards these expectations, and functional foods form a significant multimillion dollar growth category. Fortified with added health-giving compounds, these foods are promoted as the modern, convenient way of obtaining health benefits from food intake itself, rather than from the use of vitamin supplements (Grunert, 2013). However, there are indications that their appeal and usage varies considerably across nations. Somewhat surprisingly, few studies have considered functional food consumption through a culturally mediated lens, as consumption entities used to convey and transfer meaning. This research explores personal meaning making for one such proposed functional food concept. Foods which are fortified to enable greater control over hunger control are currently under development as potentially assisting those seeking weight loss. The data consisted of 14 in-depth phenomenological interviews with New Zealand women who were attempting weight loss. Participants discussed their lived food and weight loss experiences and then freely responded to the weight loss foods concept. The findings reveal the omnipresent nature of weight loss practices in daily lives, with the perception of success, or failure, sometimes underpinning one’s sense of self. As found by Willis & Knobloch-Westerwick (2014), motivations for weight loss were dominated by appearance and body image concerns, driven by the continuation of persistent societal expectations privileging thinness. Extending this, the present research found a conflation of motivations where slimness was seen to equate to healthiness. A line of progression in the types of practices was revealed where many ‘fad diets’ were attempted with typically unsuccessful long term results. Although, healthism was internalised as an overriding way of thinking about food and weight loss practices, paradoxically, this often co-existed with the desire for foods of indulgence, especially for those identifying as emotional eaters. Vastly different dispositions were revealed towards the proposed innovation of the fortified weight loss foods. These were interpreted as being aligned with perceptions of identity (Tajfel & Turner, 1986). Whilst the overall fortification of foods was viewed negatively, risks and doubts were mitigated in some cases in the interest of trying the proposed foods. The research findings resonated with societal contradictions observed for food consumption (Warde 1997), and paradoxes specifically theorised for technology (Mick & Fournier, 1998). Although, technology has been theorised to be a positive enabler in consumers’ lives, offering feelings of freedom, competence, and control, it can also be regarded as an intrusion, leading to feelings of enslavement and incompetence (Mick & Fournier, 1998). Whilst there was the promise of enhanced health and wellness from a bio-technological innovation, this contradicted central beliefs about what it means to be healthy, where food for many consumers represents values of naturalness, purity, nostalgia, and simplicity (Barsky, 1988; Biltekoff, 2010). Implications of the research for functional foods marketers are outlined, advocating the need for continuing understanding of the paradoxical aspects of consumption in contemporary health contexts.