Summary
"We Should Hang Out Sometime" is a humorous and heartfelt memoir by Josh Sundquist, detailing his quest to understand why he never had a girlfriend. At twenty-five, Josh realizes that despite his best efforts, he's always been on the outside of romantic relationships. Armed with his analytical mind, usually reserved for math and science, he embarks on a scientific investigation into his past, tracking down the girls he attempted to date from middle school through college. His goal is to identify what went wrong and, more importantly, what's 'wrong' with him.
The memoir delves into Josh's history, starting with his early experiences in middle school, navigating the complexities of church youth groups and the social hierarchy. He revisits his attempts to connect with Sarah Stevens, dissecting the nuances of truth or dare and mixed signals. He recounts his ill-fated par-three golf outing with Francesca Marcelo, a girl he deems a mystery and a challenge, as he tries to reconcile his idealized vision with the awkward reality. His forays into high school relationships are marked by both humorous mishaps and poignant realizations about his own insecurities.
As Josh progresses through high school and into college, he meets Evelyn Williamson, a close friend with whom he shares a deep connection. He navigates the friend zone, grapples with unrequited feelings, and learns valuable lessons about the importance of being genuine. College brings new challenges and new potential relationships, including his pursuit of Lilly Moore, which leads to both comical and heart-wrenching moments. His attempts to impress her through grand gestures often backfire, underscoring his tendency to overthink and analyze his interactions.
Later, the story follows Josh as he moves to Los Angeles and meets Sasha Wright, a Miss America contestant who seems genuinely interested in him. He makes a grand gesture to surprise her at the pageant, but things don't go as planned, leading him to question his ability to accurately assess relationships. It's only after a long journey of self-reflection and humorous encounters that Josh realizes his lack of success in romance stems from his own insecurities about his amputation. Rather than a fatal flaw, he discovers it was his belief in a flaw that kept him from forming meaningful connections. In the end, Josh finds love with someone who accepts him for who he is, leg or no leg. The journey underscores the importance of self-acceptance and the realization that true connection comes from genuine self-understanding.