Six summers earlier, Poppy and Alex are both low on money, so their usual summer trip is already uncertain when a resort in Vail offers Poppy a free stay. The offer arrives while Poppy is still reeling from Guillermo ending their relationship soon after she moved into his apartment, leaving her to pay for another move, a more expensive apartment, and replacement furniture.

Poppy traces the breakup back to Guillermo’s visit to Linfield for her mother’s birthday. She worries about how her loud, cluttered, eccentric family will be judged, but she refuses to warn Guillermo because doing so feels disloyal. When Guillermo says he finally understands why Poppy "fled" to New York, Poppy hears pity instead of love and feels ashamed for having exposed her family to that judgment. She tries to push past it, but after feeling out of place again at a wealthy dinner party with Guillermo’s friends, Guillermo breaks up with her, saying they are too different.

After moving out, Poppy takes one of Guillermo’s expensive knives as a small act of revenge, then spends weeks crying and trying to recover. The breakup leaves her financially strained, but money is not the only reason the summer trip may fail. Alex is now in a serious relationship with Sarah Torval, who moved to Indiana to be with him, and Poppy suspects Sarah is uncomfortable with Alex and Poppy’s unusually intense friendship.

When Alex admits Sarah feels weird about the Summer Trip, Poppy agrees that she would feel the same in Sarah’s place. Poppy recognizes that their friendship has already narrowed into brief phone calls and cat updates, and she privately admits there has always been some unresolved "what if" between them. Alex and Poppy consider inviting Sarah or canceling the trip, but neither can decide, and the conversation ends unresolved. Soon after, Poppy gets the Vail offer, breaks their long texting silence, and asks Alex to call so she can pitch Colorado.