Natalie Simmons is the driven host of a San Francisco-based lifestyle television show and likes to control as much of her persona as she can. That control gets her into trouble as a few weeks before Valentine's Day: she's fired, arguably as the ratings have declined because she's no longer being authentic--thus, no longer connecting with her audience. Only telling her parents Alicia and Aaron Simmons, Natalie heads to her small hometown just outside of Portland to regroup, and to help with the town's annual Valentine's Day Festival co-chaired by Alicia.
The trip is despite her boyfriend of two years, the show's director Brooks, needing to stay in San Francisco over Valentine's Day. Natalie has never gone back home since high school, solely to avoid her high-school sweetheart, artist Zach Williams, after their less-than-smooth breakup when he went to Europe to pursue his art degree and wouldn't allow her to follow him instead of taking her first job in San Francisco.
Natalie knows that Alicia is still friends with Zach's mother Sue Williams, the other co-chair; what she doesn't know is that Zach no longer works as a professional artist after buying the local hardware store, and that Alicia and Sue have always thought that Natalie and Zach were perfect for each other and that they're now planning to do whatever they can to reunite them. At least they can make them spend time together in manipulating the two to organize the festival's auction, which funds the following year's festival.
Natalie and Zach's time together is filled with the tension of not wanting to dwell on their painful past, but it makes Natalie reevaluate her life, including her relationship with Brooks. What may ultimately affect Natalie and Zach's relationship is whether she ever learns the truth about why he didn't want her to follow him to Europe.