2007 (original timeline)

After being shot by Ben Linus (Michael Emerson) in the episode "Dead Is Dead", Desmond Hume (Henry Ian Cusick) awakens to discover that Charles Widmore (Alan Dale) has brought him back to the Island. Desmond attacks Charles, who tells him the Island is not done with him, and that unless Desmond helps him, everyone he loves will be gone forever. He has his team prepare an electro-magnetic test, which kills a team member in the path of the toroids as they set up. Desmond is bound to a chair and locked in with the toroids as the test is run. After Desmond survives the test, he agrees to help Charles. As Charles' team leads him away, they are ambushed by Sayid Jarrah (Naveen Andrews), who takes a willing Desmond away with him.

2004 (flash-sideways timeline)

Desmond arrives in Los Angeles at the behest of his employer, Charles Widmore. After helping the heavily pregnant Claire Littleton (Emilie de Ravin) to get her luggage, Desmond goes to Charles' office. Charles informs Desmond that his son Daniel Widmore (Jeremy Davies), a classical musician, has invited the rock band Drive Shaft to perform alongside him that evening. The band's bass guitarist, Charlie Pace (Dominic Monaghan), has been arrested for possessing drugs, and Charles requires Desmond to collect and deliver him to Daniel's event.

Upon their meeting, Charlie tells Desmond that he recently almost died after swallowing a bag of heroin (As seen in "LA X"), and in his near-death state experienced an intense, blissful vision in which he was with a blonde woman. He causes Desmond to crash his car into a nearby marina, and while Desmond attempts to rescue Charlie from the water, he too experiences a vision, seeing Charlie drowning with the words "Not Penny's Boat" written on his palm. The two are taken to a hospital, where Desmond has a short series of visions of Penny (Sonya Walger), a stranger to him, during an MRI test.

After discharging himself from the hospital, Desmond apologizes to Charles' wife Eloise Widmore (Fionnula Flanagan) for being unable to ensure the attendance of Drive Shaft. Nearby employees are discussing the guest-list for Daniel's concert, and Desmond hears the name Penny mentioned. Eloise refuses to let him see the list, and warns him off of pursuing his inquiries.

As Desmond prepares to leave, he is stopped by Daniel, who tells him that he recently saw a red-haired woman in a local museum that he strongly felt he already knew and loved. Daniel states that after the encounter, he made a series of notes in his journal which a mathematician friend has identified as advanced quantum mechanics, a topic he knows nothing about. Daniel shows his notes which contain a graph with imaginary time on one axis, and hypotheses that the world as he and Desmond are experiencing is not their correct path, and something massive, like a nuclear explosion, has altered their realities. Desmond questions Daniel as to whether he intends to set off a nuclear bomb, to which Daniel replies he believes he already has.

Daniel tells Desmond that Penny is his half-sister, and tells him where he can find her. Desmond locates Penny running the steps of an athletics stadium, and introduces himself. After shaking Penny's hand, Desmond passes out. When he awakens, he asks Penny out for coffee, an invitation which she accepts. As his driver George Minkowski (Fisher Stevens) takes him to their meeting point, Desmond asks him to acquire the flight manifest for Oceanic 815, the flight which brought him to Los Angeles. When Minkowski asks why he needs it, Desmond responds, "I just need to show them something".