We Should Hang Out Sometime summary

The Curious Relationships of Josh Sundquist

In We Should Hang Out Sometime, author Josh Sundquist takes us through an investigative journey about his past relationships. After realizing at the age of 25 that he has never had a girlfriend, he approaches this issue like a scientific problem, seeking to understand what went wrong in his past flings. The book begins with Josh using a flowchart to retrospectively dissect each of his failed relationships, ranging from elementary school crushes to what he thought were serious connections in early adulthood.

Each chapter is dedicated to a particular girl and relationship. These stories take us back to Josh's young life, which was dramatically marked by the loss of his leg to Ewing's Sarcoma at the age of nine. Combining self-deprecating humor, brutal honesty, and earnest reflection, Josh explores why each romantic prospect didn't blossom into a true relationship. He chronicles his dates, interactions, and corresponds with the girls from his past while candidly discussing his insecurities about his disability and his career as a motivational speaker and Paralympic athlete.

The Shocking Discovery

Josh's analyzation process reveals a startling pattern - in several instances, he was unaware of a girl's interest in him, potentially missing many romantic opportunities. This revelation unsheathes deeper issues regarding Josh’s self-perception and instigates a profound introspection about his own actions. He reflects upon his tendency to sabotage his own chances of romantic success possibly because of his insecurities and the fear of rejection.

In a poignant turn, We Should Hang Out Sometime becomes more than just an investigative memoir; it explores deeper themes about understanding oneself, overcoming one’s fears and embracing vulnerability. Through his unique quest for answers, Sundquist emphasizes that embracing our flaws and learning from our experiences is more important than finding easy answers.

The Well-Timed Miracle

In the latter part, Sundquist shares about an unexpected encounter at a speaking event which leads him to meet his future wife, Ashley. Despite a rocky start, and in spite of the patterns from his past, Josh learns to understand and overcome his anxieties. Ashley's unwavering acceptance of Josh, limb and all, paves the path towards Josh's realization that he is worthy of love - a journey that is more significant than his original quest for answers.

Through telling the story of his eventually successful romance with Ashley, Josh displays a commendable amount of growth. He learns to stop obsessing over 'what went wrong' in the past and instead, embraces the possibility of 'what could go right' in the future. The lessons he learns offer valuable insights to readers about overcoming personal insecurities and the importance of self-love in forming meaningful relationships.

Moving Forward

We Should Hang Out Sometime concludes with Sundquist summarizing his experiences and the lessons learned. He emphasizes that despite its seeming oddity, his approach in discerning his relationship mistakes was an act of self-discovery and emphasizes the importance of addressing insecurities and fears to build stronger relationships.

Ultimately, Sundquist's story serves as a reminder that it is only through dissecting our failures and facing our fears that we ultimately discover our self-worth and capability for love and happiness. His story encourages us not to obsess over ‘why we are alone’ but to focus on understanding and improving ourselves, preparing us for the relationship that will potentially last a lifetime.