En el trancurso de un vuelo de Los Angeles a Nueva York Oliver y Emily se conocen y conectan. Los siguientes siete años se entrablará una relación que pasa de la amistad... al amor.
 | Ashton Kutcher | Oliver Geary |
 | Amanda Peet | Emily Friehl |
| Kathryn Hahn | Michelle |
| Kal Penn | Jeeter |
 | Ali Larter | Gina |
| Taryn Manning | Ellen Geary |
| Gabriel Mann | Peter |
| Jeremy Sisto | Ben |
| Rick Overton | Tailor |
| Aimee Garcia | Nicole |
| Lee Garlington | Azafata |
| Tyrone Giordano | Graham Martin |
| James Read | Brent Friehl |
| Molly Cheek | Christine |
| Amy Aquino | Diane Martin |
| Josh Stamberg | Michael |
| Sarah Shahi | Starlet |
| Moon Bloodgood | Bridget |
| Robert Peters | Roy Douglas |
| Holmes Osborne | Stephen Martin |
| Nealla Gordon | Catering |
| Sean Smith | Abogado |
| William Stanford Davis | Sacerdote |
| Meghan Markle | Chica caliente |
