Conrad Valmont, played by Jason Bateman, lives a life of luxury as a New York City debutante, raised in the lap of his family's wealth. Unfortunately, his upbringing left him feeling isolated, with his parents frequently absent on worldwide trips, leaving him in the care of their staff. This disconnect shaped his character, leading to overwhelming separation anxiety as he casually engages with various women, yet remains emotionally distant from them. Seeking clarity, he often visits his therapist Barry, who listens as Conrad grapples with his feelings of attraction, noticing a troubling pattern—he is drawn to women he doesn't care for, while those he genuinely cares for elude him.
Amidst these challenges, Conrad finds himself financially stranded after his parents cut him off, leaving him with nowhere to go. A fortuitous subway ride brings him into the orbit of Beatrice Fairbanks, portrayed by Olivia Wilde, a captivating woman engrossed in "Sense and Sensibility." Their brief exchange leads to Beatrice slipping her phone number to him, igniting a connection that veers into uncharted territory.
Conrad ends up crashing with his best friend Dylan Tate, played by Billy Crudup. The duo grapples with envy over each other's lifestyles until fate propels them into a party where Beatrice is present. The audience learns that Beatrice is a talented pianist who has ventured into modeling, but she is already entangled with Dylan, adding an awkward twist to their budding relationship. Despite this, sparks fly, and Conrad and Beatrice begin a clandestine affair, much to the chagrin of Dylan, who had warned Conrad against pursuing her.
The stakes rise as the trio navigates their tangled emotions, leading to one disastrous outing where tensions boil over. After an explosive revelation about his financial woes, Beatrice, caught in the middle, decides to break things off with Conrad. Going his separate way, Conrad suffers a devastating accident, leaving him to confront the fragility of his relationships.
Once he recovers, he attempts to mend fences with both Beatrice and Dylan. An emotional last date with Beatrice ends in a bittersweet farewell, marking a poignant conclusion to their romance. Even as Dylan begins to forgive him, Conrad remains haunted by memories of Beatrice. With his world slowly unraveling, he seeks solace in unexpected places, culminating in the completion of a book that draws from his experiences with her, although it receives only a lukewarm response.
In a twist of fate, Conrad orchestrates a reunion between Dylan and Beatrice, allowing for new opportunities as they discover success together as a jazz duo. Now, at the age of 42, Conrad finally comes to terms with his past, embracing the maturity he has long sought. Through heartbreak and recovery, he embarks on a journey toward self-realization, ready to face whatever life brings next.
