Tess had been on track to marry Josh since the day they had met in high school twenty years ago. He had been the only man she had ever loved, and the day was quickly approaching. In anticipation of their wedding, Tess and her sister are taking the train across America for a bachelorette weekend in wine country. Her trip is sure to be a time filled with friends, laughs, and memories.

Until Tess unexpectedly meets Sam, who is also traveling on a train from the east coast to the west coast. Sparks fly, and as the two begin to spend more time with each other during their cross-country journey, Tess begins to doubt her devotion to Josh as her feelings for Sam grow stronger.

The romance between Tess and Sam is bound to veer off course, though, because Tess has been keeping her engagement a secret from Sam, along with the reason she is even on the train. Unknown to the both of them, however, is the fact that their lives have already intersected in the past. If the truth came out, would it affect their feelings for each other?