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While the digitalization of intimacy has fundamentally reshaped youth dating culture, a novel phenomenon has emerged in contemporary China where parents are actively taking over digital screen spaces to find spouses for their adult children. Drawing on 24 semi-structured interviews with parent users, this article investigates how parents navigate online matchmaking platforms on behalf of their offspring. The results show that parents are driven by depleted offline social capital and a structural “inverted family” dynamic, where they bear intense responsibility without corresponding authority. Rather than blindly trusting or completely dismissing these technologies, parents act as sober gamblers. They approach online matchmaking with a hyper-rational and calculated skepticism, utilizing the platforms less as a guaranteed path to marriage and more as an anxiety-regulation tool to manage structural pressures and generational boundaries. Their practices are characterized by mosaic modernity and bricolage, as they creatively combine traditional matchmaking values with digital platforms and produce diverse intergenerational outcomes ranging from enhanced intimacy to temporary estrangement. These findings complicate narratives of either individualization or tradition persistence, revealing instead a hybrid, negotiated, and emotionally ambivalent reality. By exploring this parent-platform intersection, the article reveals how traditional kinship obligations adapt to modern digital infrastructures, advancing understanding of how digital technologies are reshaping mate selection, family dynamics, and intergenerational relations in contemporary China.