Various communication systems have been developed to integrate the haptic channel in digital communication. Future directions of such haptic technologies are moving towards realistic virtual reality applications and human-robot social interaction. With the digitisation of touch, robots equipped with touch sensors and actuators can communicate with humans on a more emotional and intimate level, such as sharing a hug or kiss just like humans do. This paper presents the design guideline, implementation and evaluations of a novel haptic kissing machine for smart phones -the Kissenger machine. The key novelties and contributions of the paper are: (i) A novel haptic kissing device for mobile phones, which uses dynamic perpendicular force stimulation to transmit realistic sensations of kissing in order to enhance intimacy and emotional connection of digital communication; (ii) Extensive evaluations of the Kissenger machine, including a lab experiment that compares mediated kissing with Kissenger to real kissing, a unique haptic Turing test that involves the first academic study of human-machine kiss, and a field study of the effects of Kissenger on long distance relationships. The first experiment showed that mediated kissing with Kissenger elicited similar ratings for pleasure, arousal and user experience as real kissing. Experiment 2 confirmed our hypothesis that interrogators have a higher chance of winning the Imitation Game (Turing test) when Kissenger is used during the game. Results from experiment 3 showed that long relationship couples who used Kissenger for a week experienced increased relationship satisfaction and decreased perceived stress.INDEX TERMS Force feedback, haptic interfaces, human-robot interaction, remote kissing, Turing test.