Ramsey Price has it all: her dream job as a history museum archivist, a rowhouse in Philadelphia with her favorite brother, Sean, and to top it off, a steady relationship with the most eligible bachelor in the city. But when a dinner with her boyfriend doesn't go as planned, she ends up single and consequently dateless to Sean's upcoming wedding in their hometown in Maine. As if things aren't bad enough, her brother asks his best friend to drive her to Portland when work delays his trip.

Since her first semester in college, Ramsey has despised Nico Giovanni. His unspoken rejection and standoffishness have never been addressed and now that she lives in Philadelphia, his stomping grounds, she's forced to see him regularly. But Ramsey refuses to let Nico win, so she reluctantly agrees to the road trip with him.

Not wanting to deal with her six brothers' relentless teasing or succumb to her mother fixing her up with one of her friends' sons now that she's single, she lies and says she's dating Nico to get them off her back.

Surprisingly, Nico agrees to be her boyfriend for the five-day-long weekend. As each day passes, she realizes Nico might not be the same guy he was in college and worse, the feelings she thought she'd buried for him years ago are alive and well. Before she knows it, the line between what is fake and what is real is blurred and she's not sure she can survive if Nico breaks her heart a second time.