S1, E2: When Whitney (Whitney Cummings) realizes that she and Alex (Chris D’Elia) have never gone on an official first date, she comes up with an unusual idea to recreate the past. Taking this very seriously -- as only Whitney can -- she insists that they follow all of the "rules" of a first date, thus the two awkwardly go to dinner and cap off the night by sleeping in separate apartments. This gives Alex and Mark (Dan O'Brien) a rare opportunity for some much needed guy time. Meanwhile, totally embodying a post first date attitude, Whitney and Roxanne (Rhea Seehorn) spend some quality girl time plotting Whitney's next move with the "new guy," but when Lily (Zoe Lister-Jones) finds out what's going on she recruits Neal (Maulik Pancholy) to help her stage a "chance" encounter between the two lovebirds.