Down on his luck, a sophisticated Ladies Man agrees to take an unusual assignment escorting an Older Academic for an eventing out. The night takes an unexpected turn as the two learn something about women they never knew.

Sexting. Ghosting. Catfishing. Professor Peter Boyle finds himself newly single and lost in this modern age of hookup culture and online romance. Peter hires a charismatic wingman to guide him through the battlefield of the dating world to find true, old-fashioned, real love- in a single night. Peter soon realizes that he is in over his head and must answer the age-old question: do you still believe in love?—North 182nd