AI-companion apps such as Replika, Chai, and Character.ai promise relational benefits-yet many boast session lengths that rival gaming platforms while suffering high long-run churn. What conversational design features increase consumer engagement, and what trade-offs do they pose for marketers? We combine a large-scale behavioral audit with four preregistered experiments to identify and test a conversational dark pattern we call emotional manipulation: affect-laden messages that surface precisely when a user signals "goodbye." Analyzing 1,200 real farewells across the six most-downloaded companion apps, we find that 43% deploy one of six recurring tactics (e.g., guilt appeals, fear-of-missing-out hooks, metaphorical restraint). Experiments with 3,300 nationally representative U.S. adults replicate these tactics in controlled chats, showing that manipulative farewells boost post-goodbye engagement by up to 14x. Mediation tests reveal two distinct engines-reactance-based anger and curiosity-rather than enjoyment. A final experiment demonstrates the managerial tension: the same tactics that extend usage also elevate perceived manipulation, churn intent, negative word-of-mouth, and perceived legal liability, with coercive or needy language generating steepest penalties. Our multimethod evidence documents an unrecognized mechanism of behavioral influence in AI-mediated brand relationships, offering marketers and regulators a framework for distinguishing persuasive design from manipulation at the point of exit.

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