Plot
Poppy Wright is a New York City-based travel writer, though she has grown unhappy with her life. When her friend David reminds her of his upcoming wedding in Barcelona, Poppy realizes it is an opportunity to reconnect with David's brother, her former best friend Alex Nilsen, with whom she has not spoken in two years. She calls Alex, falsely telling him that she is going to Barcelona for work, so she will be attending the wedding.
Poppy and Alex's history is revealed in a series of flashbacks. They met nine years prior at Boston College, becoming friends over a prolonged road trip back to their shared hometown of Linfield, Ohio. They are forced to share a hotel room, though Alex is careful to consider his girlfriend Sarah.
The following year, Poppy takes Alex camping in Squamish, following his breakup with Sarah. They are invited to join a group of partying campers. However, rather than have casual sex with other people, the two return to their tent and commit to annual summer vacations together.
In the present, Poppy and Alex awkwardly reunite in Barcelona. The two recall a trip to New Orleans six years prior, during which they pretended to be on their honeymoon, despite Alex having reconciled with Sarah and Poppy dating a man that Alex disliked. While attempting to fix the air conditioning in Poppy's hotel room, Alex has a back spasm and is forced to rest. They remember the time they planned to go to Norway four years earlier, but Poppy fell ill, so Alex elected to come to New York to take care of her instead.
Alex invites Poppy to the rehearsal dinner, but learns that she lied about being in Barcelona for work. He questions her motives, and Poppy admits that she wants them to return to how they were before their Tuscany trip, but Alex cannot.
Two years earlier, Alex and Poppy visited a Tuscan villa along with their significant others, Sarah and Trey, Poppy's co-worker. After Alex discreetly helped a frightened Poppy with a pregnancy test, they nearly kissed; Poppy claimed that she did not mean it, and Alex stormed off. The following morning, Alex proposed to Sarah, who accepted. Alex told Poppy that he and Sarah plan to settle down in Linfield together, though Poppy objected, believing it is not what Alex truly wanted. Offended, Alex declared that this is their last trip together.
In the present, Poppy presses Alex on his breakup with Sarah, and he finally admits it was because of Poppy. They declare their love for one another, have sex and attend the wedding together. At the reception, Alex asks about their future together, and is offended when Poppy says she wants time to figure things out. He accuses her of not knowing what she wants and running away from her problems through vacations, while she disparages his insistance on staying in Linfield.
At the airport, Poppy runs into Sarah. Poppy apologizes, but Sarah assures her the breakup was not just because of Alex's relationship with Poppy, as she did not know what she wanted out of life. Poppy resigns from her job and travels to Linfield. Confronting Alex, she admits her fear of being "too much" for Alex and reaffirms her desire to stay with him.
Some time later, Alex moves to New York City to build a life with Poppy, and they resume their vacations together.
