Technology now plays a central role in modern romantic relationships. From seeking romantic partners to maintaining closeness across distance, digital platforms offer unprecedented opportunities to transcend physical and temporal boundaries. Yet, despite its growing use, public and academic discourses often focus on what is lost, highlighting superficiality, emotional disconnection, and risk. This contradiction, marked by increased dependence on and resistance to technology, underscores the importance of understanding how the phenomenon is experienced from the person’s perspective. This thesis aims to explore how individuals experience and make sense of their online relationships within broader sociocultural contexts. Adopting a critical, sociocultural framework, it presents three empirical studies. Study 1 uses a qualitative, phenomenological approach to explore the lived experiences of thirteen individuals whose close relationships are primarily conducted online. Drawing on a dialogical framework, it identifies key tensions in meaningmaking across different types of relationships. Participants describe simultaneously feeling a strong connection and a sense of distance, perceiving their relationships as both deep and less real, and reflecting on the ambivalence surrounding technology’s role in relationships. The study further shows that the meanings assigned to technology shift across relational stages, from empowering and enabling in the early stages to limiting or even obstructive in later phases. It also reveals that relationships initiated through different media can carry distinct meanings. Study 2 combines a quantitative media content analysis of articles on online dating with a qualitative analysis of advice texts to examine media discourses surrounding online dating in three mainstream Irish newspapers (the Irish Examiner, Irish Independent, and Irish Times) between 2000 and 2024 (N = 846). The quantitative analysis maps thematic prevalence, evaluative tone, and the visibility of different populations over time, while the qualitative analysis explores the normative guidance offered to readers. The longitudinal analysis shows an increasing negativity in tone, even as online dating becomes more normalized and widely used. Reports often emphasize crime, risk, and inauthenticity over the relational possibilities afforded by dating apps. Since the media plays an important role in shaping and reflecting public perceptions, this study highlights how public discourse can reinforce stigma, influence personal expectations, and contribute to the ambivalence many individuals feel towards online dating. Study 3 addresses the contradiction between the prevailing negative representations of online dating and the widespread use and relational benefits associated with these technologies. Using a story completion, comparative betweengroups experimental design (N = 537), the study investigates implicit associations between various modes of romantic initiation, including dating apps, online communities, and face-to-face meetings, and the perceived quality and longevity of resulting relationships. Notably, relationships initiated in online writing groups were associated with more negative outcomes, suggesting the persistence of implicit biases toward certain forms of online media. These studies demonstrate that technological mediation is experienced as a dynamic process shaped by personal agency, social discourses, and technological affordances. Building on this insight, the thesis concludes by proposing a conceptual model that situates individuals, their relationships, the technologies they use, and the broader sociocultural-historical context within a dynamic three-wave model. Rather than treating these as stable levels, the model shows how their relative salience shifts across relationship stages and historical moments, and how points of intersection between them shape relational experience. The findings highlight the pervasiveness of a negativity bias in public discourse and in individuals’ representations, while also showing that lived experiences are more complex and often more positive than dominant cultural narratives suggest. They therefore caution against allowing this bias to shape how online dating is experienced, interpreted, or studied. Rather than being affected by stigma or negative representations, engagement with dating apps can align with users’ relational goals and values. The findings also highlight the need for more balanced public discourse and indicate that research should move beyond technology–centered and problem–oriented framings towards approaches that address both the pitfalls and the opportunities arising from online dating.