A young man and woman meet on a cross-country flight. Oliver is a brand new college graduate with an airtight timeline for attaining his dreams of both business success and finding true love. Emily is a bold, free spirit drawn to spontaneity and wild extremes. Two different choices, two incompatible views on life. They may have hooked up for a brief moment, but Oliver and Emily clearly don’t belong together. Or do they? Though they both move on, Oliver and Emily nevertheless can’t quite seem to completely let go. As the two bump into each other, year after year, in city after city, through changing careers and different relationships, there always seems to be plenty keeping them apart. And yet, there’s also something utterly inexplicable pulling them together. There’s something about the way they laugh together, the way they can talk to each other, the way they always seem to be there for one another when things are falling apart. So what keeps getting in the way of what could be romantic destiny? As Oliver and Emily set off on their own individual paths, they move across New York, Los Angeles and San Francisco--and down the hilariously meandering road of modern love.