Sherry, the girlfriend of the former "Don Juan," a successful older businessman named Don Johnston, decides to end their relationship, leaving him at a crossroads. Compounding his emotional turmoil, Don receives an anonymous pink letter informing him of the existence of a nineteen-year-old son, yet he is clueless about the identity of the child’s mother. This prompts his friend and neighbor, Winston, an enthusiastic wannabe detective, to devise a plan for a cross-country journey to reconnect with Don's former lovers in hope of uncovering their shared past and the mystery of his son.
Initially hesitant and emotionally detached, Don embarks on his journey armed with flowers. His first encounter is with the widow Laura and her teenage daughter, Lolita. Surprisingly, Lolita confronts Don in an unexpected manner, appearing naked in what seems to be a challenge to his presence. Despite this awkward introduction, Laura proves to be the one individual who treats him with respect and acknowledges his humanity.
Next, he meets with real estate agent Dora and her husband Ron, where the atmosphere becomes increasingly uncomfortable, illustrating Don's role as an unwanted guest at their dinner table. His next stop leads him to Dr. Carmen, his ex-flame now turned animal psychologist, who inadvertently reveals the emotional gap between them, as her detached young secretary rebuffs Don's attempts at rekindling a connection. Despite his enthusiastic efforts, Don remains on the outside, with the secretary deeming his well-meant gesture of flowers as unworthy.
In his last stop, Don attempts to charm Penny, who now resides in the woods with a group of rough motorcycle riders. Yet, his interaction leads to unexpected hostility when one of the toughs confronts him, resulting in Don waking up in his car with his flowers destroyed. Presently feeling desperate, he encounters a kind-hearted florist named Sun Green, who seems to offer a glimmer of tenderness, albeit she finds Don's name rather quaint and amusing.
As Don continues to navigate through his interactions, he meets a hitchhiker, attempting to connect only to fumble through another uncomfortable moment, remarking on the hiker's fatherless upbringing. This misjudged comment leads him deeper into a realization about his own state—while he perceives his former partners as neurotic, he is similarly seen as inconsequential by the outside world. Ultimately, Don returns home empty-handed, burdened by the understanding that the past remains out of reach and irretrievably lost.
