A year after their first date, fate brings Evan and Gently back together when they run into each other at an art gallery and romantic feelings are rekindled. That chance encounter turns into a spontaneous date night, that soon takes an unexpected turn.

After three months of dating, Evan invites Gently to his parents' 40th anniversary party. What starts out as a lovely evening quickly goes awry when Evan's father has too much to drink and his mother can't hide her contempt for Gently.

On the hottest day of the year, Evan whisks Gently away to Malibu for a romantic weekend. When the trip hits the rocks, the couple is forced to question their future.

Evan takes a day away from his new tech company to help Gently make as many wedding decisions as possible, but they soon realize they have wildly different expectations for their big day.

At Evan's urging, he and Gently spend the day "shopping" for a counselor to help them address their issues, but it soon becomes apparent that their problems are deeper than either of them imagined.