Both traveling for work, in a city in which neither lives, a man (Chris Messina) and a woman (Marin Ireland) have a one-night stand. Months later, in another city, they run into each other in a hotel restaurant and sleep together a second time. Though she's married and he has a girlfriend, they decide to keep meeting. This begins an unexpected love that slowly evolves into a profound relationship and threatens to impact everything else in their lives. The film unfolds as a collage of moments -- some mundane, some profound, some silly, some intimate - that attempts to tell a more complete story of a relationship. 28 Hotel Rooms is an intimate portrait of an affair in which follows two people as they wrestle with the intoxication of love and the pain, guilt, and confusion of loving more than one person.