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People, especially young adults, often use their smartphones out of habit: They compulsively browse social networks, check emails, and play video-games with little or no awareness at all. While previous studies analyzed this phenomena qualitatively , e.g., by showing that users perceive it as meaningless and addictive, yet our understanding of how to discover smartphone habits and mitigate their disruptive effects is limited. Being able to automatically assess habitual smartphone use, in particular, might have different applications, e.g., to design better “digital wellbeing” solutions for mitigating meaningless habitual use. To close this gap, we first define a data analytic methodology based on clustering and association rules mining to automatically discover complex smartphone habits from mobile usage data. We assess the methodology over more than 130,000 phone usage sessions collected from users aged between 16 and 33, and we show evidence that smartphone habits of young adults can be characterized by various types of links between contextual situations and usage sessions, which are highly diversified and differently perceived across users. We then apply the proposed methodology in Socialize, a digital wellbeing app that (i) monitors habitual smartphone behaviors in real time and (ii) uses proactive notifications and just-in-time reminders to encourage users to avoid any identified smartphone habits they consider as meaningless. An in-the-wild study with 20 users (ages 19–31) demonstrates that Socialize can assist young adults in better controlling their smartphone usage with a significant reduction of their unwanted smartphone habits.