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.