How to Say Goodbye (2018)

Plot

Tom, a struggling bond broker haunted by his brother's 9/11 death, finds his life intertwined with Claire, a budding actress escaping her own past. As they navigate their complex emotions, Tom faces a pivotal choice: confront his fears and embrace his feelings for Claire or retreat to safety. Meanwhile, his best friend Simone grapples with an identity crisis fueled by a desire for instant gratification, while Mario, a wine-loving womanizer, navigates the pitfalls of his lifestyle. Against the backdrop of New York City, these four characters strive to shed their old selves in pursuit of a brighter future.