An LA-based animator, reeling from heartbreak, is pushed back into the dating world by his well-meaning friends. When he meets an emotionally intuitive record exec who matches his particular brand of weird, they take a spontaneous road trip along the California coast, including stops throughout SLO County and a stay at the iconic Madonna Inn. As they confront lingering pasts, HOW TO DATE AGAIN embraces the messiness of healing, vulnerability, and choosing connection.
| Actor | Role |
|---|---|
 Haley Joel OsmentHugh | Hugh |
 Natasha LoringLeigh | Leigh |
 Johnno WilsonXander | Xander |
| RRob MorMichael | Michael |
 Amanda PaytonKai | Kai |
 Kevin NealonLarry | Larry |
 Emilio RiveraRancher | Rancher |