When meeting women online for the first time in the 90s, Sean Wolf finds out why the dates with them are failing by talking to a dating coach, but he learns a life-challenging secret from a woman he met.
| Actor | Role |
|---|---|
| BBrandon Beard-ReedSean / Narrator | Sean / Narrator |
 Etalvia CashinSharon | Sharon |
| FFranshawn HullLanease | Lanease |
| CCleo PaigeRodney | Rodney |
| JJamal MannsKevin | Kevin |
| KKevin MurphyRoy | Roy |
| CCrissa JacksonBasketball Friend | Basketball Friend |