The antique green John Deere tractor, captured in Olivia’s favorite Polaroid of Annie, symbolizes the central secret of her grandmother’s past: a lost summer romance with Christian. Unlike the other landmarks in the photos, which are identifiable public places, the tractor’s location is labeled only as “Summer camp,” with no further context offered. Tracing that missing memory drives Olivia to question neighbors, cross-reference local history, and then travel to Paqua Farm, where she finds the tractor still standing.

The reveal of Annie’s past romance with Christian eventually inspires Olivia to pursue a relationship with Connor despite her past trauma and grief, underscoring the need to foster emotional connection through shared vulnerability. The tractor embodies a key, life-altering chapter that Annie kept hidden for over 50 years. Its existence reveals to Olivia that even the person she knows most intimately has their own secrets and helps her understand her grandmother as a complex woman who had her heart broken and still lived a full life, eventually meeting Olivia’s grandfather. As Christian tells Olivia, “One thing about timing […] is that it is fairly malleable. You can play with it, reshape it to your advantage […] But from what your dad told me about Annette and your grandfather. He told the timing to screw itself” (354). Christian’s words resonate with Olivia and push her to take a risk on Connor.

Jumping from the Jaws Bridge on Martha’s Vineyard is a recurring motif representing a leap of faith and the courage to confront personal fears. The bridge is introduced as “a rite of passage on the island” (56), but for Olivia, who’s afraid of heights, it presents a significant personal challenge. Her fear of the physical drop mirrors her emotional apprehension about vulnerability and trust, highlighting the novel’s thematic engagement with The Way Fear of Loss Inhibits Love.

Connor’s gentle encouragement, combined with her own growing desire to embrace new experiences, culminates in a key moment of decision. When she resolves to jump, she thinks, “When am I going to get the chance to do this again?” (123). That question signals a shift from hesitation to action, a direct confrontation with her habit of holding back. By taking the plunge with Connor, Olivia performs a symbolic act of letting go, choosing to trust both him and herself. In the moment she steps off the bridge, Olivia stops protecting herself from the risk of connection and commits to what she and Connor have started.