This article aims to investigate the portrayal of optimism in two modern films, Marc Webb’s 500 Days of Summer (2009) and Spike Jonzes’s Her (2013), using Viktor Frankl’s concept of optimism. The focus is on the characters’ quest for love and self-discovery in the midst of challenges and emotional turmoil. They present the idea of seeking purpose and personal development while experiencing highly complex emotions. Accordingly, this article scrutinises the storytelling techniques embedded in characters’ notions revealed through their progression in both films to display the intricacies of relationships in today’s world. Films play a role in deepening the grasp of the complicated themes of love, technology, and obsessive passion in today’s world, as well as shed light on persistent psychological challenges with modern ways of storytelling.