Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
| Actor | Role |
|---|---|
 Jessica WilliamsJessica James | Jessica James |
 Chris O'DowdBoone | Boone |
 Noël WellsTasha | Tasha |
 LaKeith StanfieldDamon | Damon |
 Megan KetchMandy | Mandy |
 Zabryna GuevaraMrs. Phillips | Mrs. Phillips |
 Susan HeywardJerusa | Jerusa |
 Will StephenTinder Guy | Tinder Guy |
 Anne CarneyMrs. Taggart | Mrs. Taggart |
 Taliyah WhitakerShandra | Shandra |
 Sarah JonesHerself | Herself |
 Evander Duck Jr.Kenny James | Kenny James |
 Patricia R. FloydMrs. James | Mrs. James |
 Robert KingDuane | Duane |
 Jennifer KimHeather | Heather |
 De'Jhana MooreDe'Jhana | De'Jhana |
| KKayla DíazKayla | Kayla |
| DDavion DowdellDavion | Davion |
| BBrandon S. MartinezBrandon | Brandon |
| SSelena SanchezSelena | Selena |
 Eric LoscheiderMandy's New Man | Mandy's New Man |
 Matthew MaherActor | Actor |
 Hannah BosActress | Actress |
 Gavin HaagMan on Street | Man on Street |
 Collin SmithBartender | Bartender |
| LLinda GlickWoman in Fancy Dress | Woman in Fancy Dress |
| DDana JacksClueless Guest | Clueless Guest |
 McManus WoodendThe Manspreader (uncredited) | The Manspreader (uncredited) |