The audience is introduced to Dana and Peter and will go along for the ride on their first date, hearing what they really think of each other.
Dana runs into Peter on a date with another woman, and Amy rallies Dana to start dating other people. Where does this leave things for Dana and Peter’s relationship?
Dana and Peter agree to see other people. That changes when Amy hosts a party and Peter plans to bring someone else as his date. Peter and Dana’s evenings do not go as planned.
Dana and Peter realize they haven’t had sex and decide tonight’s the night. When their dinner reservation is pushed, they head elsewhere and their evening becomes a disaster.
Dana and Peter’s latest disagreement is the romantic comedy "Love Actually". Friends plan a double date and a viewing of the flick but will good intentions lead to another quarrel?
Dana has her first book to edit but with a quick deadline, while a storm brings everyone to her office. Amy and David fight over the value of things.
Dana is forced to reveal an embarrassing hobby (LARPing) to Peter. But a supportive Peter decides to join her on the playing field. David closes a deal with an important client.
When Dana replaces Peter with Tucker as her plus one to a friend’s wedding, Peter realizes that he’d rather have a miserable time with Dana than a wonderful time without her.
Peter is embarrassed by his family and doesn’t invite Dana to Thanksgiving. But Dana's flight home gets cancelled and she ends up in the middle of a family Thanksmas tradition.
When Peter learns Dana is friends with her exes, he tries to reconnect with his one long term girlfriend. There is conflict at Cooper & Sons when Amy fills in for the receptionist.
When Dana’s ex-boyfriend shows up to win her back, Peter does everything he can to show Dana how much he cares. David helps Chloe get out of her dating slump using a family secret.