Easier with Practice (2009)

In an effort to promote his unpublished novel, Davy Mitchell sets out on a road trip with his younger brother. However, the idealism of being on the road wears off and it quickly proves to be a lonely and unfulfilling experience for Davy. One night in a motel room he gets a random phone call from a mysterious woman named Nicole. They start a funny and intimate long distance relationship that leaves Davy happier than he has been in years. Hoping there is more to the relationship then a voice and a phone bill, Davy decides he wants to meet Nicole. Ultimately, he will have to face not only the truth about their relationship but also about himself.