My Friend Friedrich (2003)

My Friend Friedrich opens on awkward, bespectacled Columbia student Nate having a heart to heart on the phone with his mother. Then, in a philosophy class, he almost succeeds in landing a date by lobbing an illustrated invitation at his love interest, Emma. All goes awry when a taller, more confident, bespectacled Columbia student cuts him off at the knees. So far, so very New York student film, but a conceit arrives to distinguish this story of Ivy League dating woes: the ghost of Friedrich Nietzsche appears before Nate to guide him towards self-actualization.

Unfortunately the movie My Friend Friedrich is not yet available on HBO Max.