Artificial Intelligence (AI) systems are revolutionizing online learning by helping instructors streamline tasks, customize student experiences, and enable adaptive assessments. AI may improve online education, but its effects on learner–instructor boundaries, cultural norms, and expectations are unknown. Learning outcomes and student satisfaction depend on learner–instructor communication, support, and presence in online learning. Artificial intelligence in online education platforms, like speed daters seeking meaningful connections quickly, may change student–teacher engagement. Identifying any boundaries, challenges, or barriers that prevent AI from reaching its full potential and compromise the safety of learner-instructor interactions requires understanding students’ and instructors’ perspectives. Speed Dating with storyboards was used to gather students’ and instructors’ real-world thoughts on AI applications in online learning to address this need for proactive decision-making. Learning platforms with AI may improve learner–instructor interaction on a large scale, like speed dating in education. Despite crossing social boundaries, personalization deepens relationships. AI has improved communication, provided timely, individualized support in large educational environments, and increased participant connectedness in online learning, but accountability, autonomy, and privacy concerns remain.