On one hand, academic and industrial researchers have been developing and deploying robots that are used as educational tutors, mediators, and motivational tools. On the other hand, an increasing amount of interest has been placed on non-expert users being able to program robots intuitively, which has led to promising research efforts in the fields of machine learning and human-robot interaction. This dissertation focuses on bridging the gap between the two subfields of robotics to provide personalized experience for the users during educational, entertainment, and therapeutic sessions with social robots. In order to make the interaction continuously engaging, the workspace shared between the user and the robot should provide personalized contexts for interaction while the robot learns to participate in new tasks that arise. This dissertation aims to solve the task-learning problem using an instance-based framework that stores human demonstrations as task instances. These instances are retrieved when confronted with a similar task in which the system generates predictions of task behaviors based on prior solutions. The main issues associated with the instance-based approach, i.e., knowledge encoding and acquisition, are addressed in this dissertation research using interactive methods of machine learning. This approach, further referred to as interactive instance-based learning (IIBL), utilizes the keywords people use to convey task knowledge to others to formulate task instances. The key features suggested by the human teacher are extracted during the demonstrations of the task. Regression approaches have been developed in this dissertation to model similarities between cases for instance retrieval including multivariate linear regression and sensitivity analysis using neural networks. The learning performance of the IIBL methods were then evaluated while participants engaged in various block stacking and inserting scenarios and tasks on a touchscreen tablet with a humanoid robot Darwin. In regard to end-users programming robots, the main benefit of the IIBL framework is that the approach fully utilizes the explanatory behavior of the instance-based method which makes the learning process transparent to the human teacher. Such an environment not only encourages the user to produce better demonstrations, but also prompts the user to intervene at the moment a new instance is needed. It was shown through user studies that participants naturally adapt their teaching behavior to the robot learner's progress and adjust the timing and the number of demonstrations. It was also observed that the human-robot teaching and learning scenarios facilitate the emergence of various social behaviors from participants. Encouraging social interaction is often an objective of the task especially with children with cognitive disabilities, and a pilot study with children with autism spectrum disorder revealed promising results comparable to the typically developing group. Finally, this dissertation investigated the necessity of renewable context for prolonged interaction with robot companions. Providing personalized tasks that match each individual's preferences and developmental stages enhances the quality of the user experience with robot learners. Confronted with the limitations of the physical workspace, this research proposes utilizing commercially available touchscreen smart devices as a shared platform for engaging the user in educational, entertainment, and therapeutic tasks with the robot learners. To summarize, this dissertation attempts to defend the thesis statement that a robot learner that utilizes an IIBL approach improves the performance and efficiency of general task learning, and when combined with the state-of-the-art mobile technology that provides personalized context for interaction, enhances the user's experience for prolonged engagement of the task.