People face choices between novelty and familiarity constantly. This work examines whether and how other ubiquitous features of life influence these choices. Chapter 1 examines the influence of social context by revealing that people are more likely to explore the unknown when known information comes from other people as opposed to non-social sources (e.g., computers). Chapters 2 and 3 examine the influence of time and sequence at different scales—the between-experience and within-experience levels, respectively. Chapter 2 examines how people facing endings show an increased desire for familiar experiences. Chapter 3 examines how people value experiences that end by reintroducing familiar elements with novel meaning, and further finds that this effect is driven by a type of social context that connects the experience architect with the experience consumer. Across these three chapters, this work demonstrates how the lenses of social context and time and sequence shape the decisions people make between novel and familiar experiences.