Will Easterly leads a great life in Chicago. The postcollege uncertainty of his twenties behind him, he's married to Rachel Armas, love of his life, and in just a few months he'll become a father too. But instead of feeling excited, he finds himself doubting his ability to be a good parent. Probably because his own dad walked out when Will was only a kid.
So the day Rachel comes home in tears, he jumps at the chance to bury his own insecurities and focus on her. Turns out she was just offered her dream job...in Los Angeles. Already overwhelmed by the prospect of motherhood, Rachel turns it down, leaving Will to worry she'll come to regret the decision.
Inspired by their binge-watching of the hit reality show Date Me Now!, Will plans a date week for Rachel: a weeklong road trip filled with adventures. But when Will uses the trip to go behind Rachel's back and get involved in her career, their future together is suddenly in doubt.