Interviews follows James as he copes with his various insecurities in a newly forged romantic relationship with Claire. From fumbling and awkward sex to trying to choose a film to watch, James struggles to connect with his new girlfriend during a single day and night in her apartment. Meanwhile he is challenged to conquer his insecurities via his subconscious.
The film is meant to explore some of the internal and external complexities involved with connecting with others, the vulnerability this generally causes, and the differences between one's expectations versus reality (and the ultimate disappointment the disjunction between the two causes), as well as how past disappointments can weigh on and affect one’s life.
It's also, in a smaller sense, meant to satirize a common type of contemporary sexist male attitude -- that somehow being a 'nice guy' is enough justification for one to be loved by someone else, when we all know it isn't.