Many people struggle with small talk, with some younger Americans admitting they simply don't know how to engage in it. A communication app called RiseGuide is testing a theory that direct experience with strangers can rebuild social confidence. To do this, they are hiring three "Chief Small Talk Officers" for a month-long paid gig. These individuals will approach strangers in public places like parks and bookstores to practice initiating conversations. They will track their progress, including conversation length and receptiveness, and self-assess their skills before and after. RiseGuide believes social confidence is trainable, not an innate personality trait, and aims to help users become comfortable with real-life interactions. The decline in opportunities for spontaneous conversations is attributed to smartphones and personalized digital feeds, which offer niche interests instead of shared cultural reference points. Even traditional social hubs like bars are seeing reduced casual interactions as people opt for their phones. This avoidance, while sparing potential awkwardness, also deprives individuals of the psychological benefits of casual encounters. Research suggests interacting with strangers can lead to more positive experiences than remaining isolated. The ultimate goal is not to become an extrovert but simply to become more comfortable with the discomfort of starting conversations with unfamiliar people.