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Three months ago

Grumpy Billionaire CEO's Nanny: An Age Gap Forced Proximity Romance

Three months ago is not merely a date marker but the story’s hinge between possibility and consequence. In that period, Indy Drake moves from performing with her guitar in a parking lot to facing a large audience, meeting Derek Joyce again, entering his household as a nanny, and becoming entangled in a relationship shaped by desire, grief, and fear. The interval gathers the encounters that make later reconciliation, professional recognition, and marriage possible.

A Singer Crossing the Threshold

Three months ago begins with Indy backstage in a dressing room, already aware that the setting is unlike the parking lot where she usually performs. Her cousin Bethany encourages her and asks whether she is ready; Indy can answer only that she is as ready as she will ever be. The contrast establishes the scale of the transition: the guitar and the familiar outdoor setting have given way to bright stage lights, curtains, and a large crowd.

When the curtains open, Indy is briefly blinded by the lights and struggles with stage fright she had not known she possessed. Bethany’s thumbs-up gives her the immediate support needed to continue. Indy closes her eyes as the music begins, then sings with enough force to leave everything onstage. The silence during the performance changes into applause when the music ends, confirming that her fear has not invalidated her talent. Bethany’s embrace backstage turns the performance into a shared victory, while the arrival of Mr. Joyce connects Indy’s artistic breakthrough to the man who will become central to her private life.

The same period also preserves Indy’s more precarious musical reality. She travels to the docks with her guitar case and returns to her usual patch of grass opposite the cruise liners, where passengers wait to board. She assembles her small stool, settles the guitar strap across her chest, and prepares to entertain strangers. Performing there is the closest she can come to her dream of singing for people across the country, or perhaps the world. The scene places ambition beside limitation: the crowd is real, but the opportunity remains improvised and uncertain.

The Earlier Encounter with Derek Joyce

Three months ago also reaches backward within the narrative to the first encounter between Indy and Derek. When Indy arrives for a nanny interview, the man who opens the door is immediately recognizable as the person she kissed three months earlier. His bright blue eyes and dark-blond hair trigger her memory of that kiss, which she has repeatedly replayed while approaching the interview. The temporal overlap makes the date emotionally unstable: the first kiss belongs to an earlier moment, yet it governs the present interview as strongly as any spoken history.

Indy attempts to conceal her shock by offering her hand and identifying herself as Indigo Drake, then asks to be called Indy because Miss Drake makes her feel old. Derek recognizes the nickname at once. His body reacts before he can control the memory of her lips, and he has to interrupt the impulse to kiss her again. The interview therefore carries two opposing identities at once: Indy is a prospective employee, while Derek already knows her as the woman from an intimate encounter. The employment relationship becomes the formal structure through which their unresolved attraction must operate.

Attraction Inside the Joyce Household

After the interview, the three-month interval becomes the foundation of Indy’s entry into Derek’s domestic world. Derek’s memory of their first kiss complicates his attempt to treat her as one employee among many, especially because she is being considered for work involving Isabella Joyce. Indy’s presence is consequently tied not only to Derek’s desire but also to the care of his daughter and the routines of the household.

The attraction repeatedly appears through physical reaction before either character fully names it. After another kiss and Derek’s abrupt withdrawal, Indy wakes with a new sense of nervousness about how he will behave. She goes to the house even though he has not said he needs her, preferring to report for a shift rather than wait in uncertainty. Derek, meanwhile, compares his desire for Indy with what he once felt for Cassidy and wonders why Indy makes him feel so out of control.

Derek interprets Indy’s arrival a few months after their first meeting as possibly meaningful, even imagining that Cassidy might be showing him that the family he wanted could still exist. That hope is immediately challenged by guilt and recurring nightmares. His life with Isabella has been deeply fulfilling, but he admits to loneliness and to missing someone with whom he can share his life. Three months ago therefore marks the point at which companionship becomes imaginable again, while Derek’s grief still makes that possibility feel morally dangerous.

The relationship also acquires the gestures of a date before it can be openly acknowledged as one. Derek drives Indy into Miami and takes her to Nigel’s restaurant. He opens the car door for her, offers his hand, and maintains the contact as they enter. When the hostess pays attention almost exclusively to Derek, Indy becomes jealous and wonders whether he would rather have someone like the hostess beside him. Derek recognizes the reaction and tells her, "I like seeing you jealous." The moment converts jealousy from a private insecurity into mutual evidence of attraction, even as the workplace and household context continues to make that attraction forbidden.

From Rupture to Deliberate Commitment

The emotional consequences of this period are not limited to romance. After Derek and Indy spend the night together, Cassidy appears in his nightmare. The next morning he pushes Indy out of his house and tells her that the night was a mistake. When Jacob Joyce confronts him about what happened, Derek admits both the nightmare and the rejection. Jacob points out that Cassidy has been gone for twelve years and that Derek himself is the person preventing a new relationship. Isabella’s needs and happiness become the practical measure Jacob urges Derek to consider, and Derek acknowledges that his brother is right.

That acknowledgment eventually becomes action. Derek tells Indy that Cassidy died from a complication during childbirth, receiving only the first day of Isabella’s life before she was gone. He explains that his nightmares have continued and that the latest one frightened him more than the others. Rather than treating the confession as an excuse, he promises to seek help for his emotions about Cassidy and tells Indy that he genuinely wants their relationship to work. He has also spoken with Isabella, who supports him as long as he is happy.

Derek specifically promises that fear will no longer result in abandonment. If the same pain occurs again, he says he will talk it through with Indy instead of pushing her away. He schedules an appointment after bringing Isabella home and admits that he does not want to lose Indy. Their reconciliation changes the meaning of the earlier interval: the same attraction that once produced secrecy and retreat becomes the basis for communication, treatment, and a chosen future.

The change reaches Derek’s dreams. After falling asleep beside Indy, he experiences a vision of her holding their baby, an older version of that child beside Isabella, and the pair of them watching future descendants play in a yard. The dream does not erase Cassidy, but it alters her place in his imagination. Derek hopes she will encourage the life he is trying to live rather than pull him back into the grief that has governed him. Three months ago thus contains the beginning of a movement from survivor’s guilt toward hope, without presenting happiness as effortless or free of the past.

The Interval’s Lasting Significance

The period culminates in a performance that joins Indy’s career and her relationship. With Bethany beside her and Derek and Isabella in the audience, Indy walks onto the stage and dedicates the first song to a special person in the crowd. She sings John Legend’s "All of Me" while looking toward Derek, then completes the rest of her lineup with renewed energy. Derek responds by embracing her, spinning her around, and kissing her, publicly confirming the affection that earlier scenes forced them to conceal.

The final transformation of the interval is Indy’s proposal. After telling Derek that she loves him and hearing him say that he loves her too, she asks him to marry her. Derek jokes that the proposal should have been his line, but Indy keeps the initiative and points to the ship as the place where everything first began for them. Her request turns the earlier encounter into a shared origin story: what started as a kiss connected to a performance and an unstable employment arrangement is reimagined as the beginning of marriage.

As a temporal designation, three months ago therefore carries the story from public vulnerability to private intimacy, from improvised music to professional performance, and from Derek’s fear of replacing Cassidy to his willingness to pursue happiness. Its decisive significance lies in how many later identities are seeded within it: Indy as singer, nanny, partner, and prospective wife; Derek as grieving widower, father, patient seeking help, and future husband; and Isabella as the child whose acceptance helps make the reconstructed family possible.