When do Will and Natalie get together is the central question that drives the emotional arc of the series. Fans analyze every interaction, searching for the subtle cues that hint at their eventual connection.
The timeline of their relationship unfolds through key milestones that redefine the story. Below is a structured overview of the most important phases and turning points in their journey.
| Phase | Key Event | Will's Role | Natalie's Role |
|---|---|---|---|
| Season 1 Introduction | First encounter at the office party | Reluctant admirer | Guarded professional |
| Season 2 Development | Collaboration on high-stakes project | Protective partner in crisis | Slowly lowering defenses |
| Season 3 Turning Point | Misunderstanding leads to temporary split | Realizes deeper feelings | Confronts emotional fears |
| Season 4 Resolution | Joint decision to pursue relationship | Takes initiative to reconcile | Accepts vulnerability |
Will's Internal Conflict About Commitment
Will's hesitation shapes much of the early tension between the characters. His past relationship trauma makes it difficult for him to trust Natalie fully, even when he cares deeply about her. Viewers watch as he gradually learns to communicate his fears instead of running away.
Natalie's Guarded Optimism
Natalie enters the connection with cautious hope. She has been hurt before and is wary of moving too fast, yet she cannot ignore the strong chemistry and shared values between them. Her journey focuses on balancing self-protection with the possibility of genuine love.
Shared Challenges That Bring Them Closer
External pressures force Will and Natalie to rely on each other in meaningful ways. A demanding project at work tests their professional boundaries, while a family crisis reveals their emotional strengths. These shared trials become the foundation for mutual respect and vulnerability.
Key Relationship Milestones
- First honest conversation about intentions in Season 2
- Joint decision to prioritize their partnership over external pressures
- Public acknowledgment of their relationship at the office event
- Mutual apology and recommitment after the Season 3 misunderstanding
FAQ
Reader questions
Why does Will pull away right when things start to get serious with Natalie?
Will pulls away because he associates closeness with loss of control, a pattern from his previous relationship. Instead of facing that fear, he distances himself, which temporarily stalls their progress.
Does Natalie ever consider giving up on Will after his repeated hesitations?
Natalie briefly considers stepping back, but her strong emotional investment and belief in second chances keep her engaged. She sets clear boundaries to protect her own well-being while remaining open to change.
What finally makes Will acknowledge his feelings for Natalie in Season 2?
Will acknowledges his feelings after seeing Natalie support him during a public failure. Her unwavering loyalty contrasts with the judgment he expects, prompting him to admit what he wants.
How do fans react to the moment Will and Natalie officially become a couple?
Fans celebrate the moment as a long-awaited payoff, praising the gradual buildup of trust and emotional honesty. Many highlight the scene where they choose each other despite uncertainty as a turning point for both characters.