Flash-sideways timeline (2004)
Desmond is examining the Oceanic Airlines arrivals board. Hurley passes and tells him the luggage is on carousel 4. At the carousel Claire is struggling with her baggage and Desmond helps her. He asks whether she is expecting a boy or a girl and when she says she doesn't know he says she is braver than he as he is not a fan of surprises. He offers her a lift and after she refuses he says that he bets the baby is a boy.
Desmond is met by George, his driver. He asks to be taken to the office. George offers lovely ladies for companionship and when Desmond says he is here to work George says that that is why Desmond is the bosses right hand man and he is the driver.
At the offices Desmond and Widmore greet each other warmly. Desmond looks at a sailing ship model as Widmore speaks on the phone saying to "Get him arraigned and get him out of there". Widmore explains that his son, the musician wanted to combine classical music with Rock at a charity event that Mrs Widmore is hosting. He says that the base guitarist for Driveshaft overdosed and was arrested, he asks Desmond to babysit the guitarist and get him to the event otherwise Mrs Widmore will destroy him. When Desmond agrees to help Widmore is grateful that someone he trusts will do the job and adds that Desmond really has the life being free of all attachments. Widmore pours a 60 year old MacCutcheon whiskey to celebrate Desmond's indispensability.
Desmond drives to the Courthouse. An attorney comes out with Charlie Pace. Desmond introduces himself but Charlie ignore him and walks across the Avenue oblivious to the traffic. He walks into Jax, a bar, and Desmond joins him. Charlie asks him if he is happy, and when Desmond reels off evidence of his material success Charlie says that what he is talking about is "spectacular, consciousness altering love". Charlie tells a story about how he saw a woman in a dream while he was about to die from choking on the bag of heroin. Charlie says "I've seen something real. I've seen the truth." Desmond says the real truth is not this vision of love but to make a choice between continuing to drink or coming with Desmond to play at the charity show - with all its trappings.
As they drive away Charlie tells Desmond that the song on the radio is Driveshaft's first single and says ruefully that it was the beginning of everything great. Charlie then offers Desmond a choice between showing him what he is talking about or getting out of the car. Charlie grabs the steering wheel and they career over a pier into the water and the car sinks. Desmond frees himself and when he can't release Charlie's seat-belt he swims to the surface exiting through his open driver's side window. Desmond dives back and goes to Charlie's door. Charlie wakes, and staring at Desmond raises his palm to the window. For a moment Desmond sees Charlie show his palm at the Looking glass hatch with the words "NOT PENNYS BOAT" written on his palm. He looks again and the vision has passed. Desmond gets the door open and brings Charlie to the surface.
A doctor examines Desmond. She asks whether he has had hallucinations, Desmond pauses and says that he's not sure. The Doctor wants to do an MRI scan but Desmond says he doesn't have time and needs to find the person he was brought in with but the Doctor insists he have the MRI.
Desmond is prepared for the MRI by a technician. He's given a panic button and the test is started. Desmond immediately sees the vision of Charlie at the Looking Glass hatch showing the message on his palm. He then sees a glowing cavalcade of his life with Penny and their love for one another. Desmond presses the panic button and says he must find Charlie.
Shortly after he asks at the nurses desk after Charlie but is rebuffed. He sees Jack and reintroduces himself. As Desmond asks Jack for help finding Charlie, Charlie runs down the passageway pursued by an orderly. Desmond gives chase and when he corners him Charlie says he is running because no one at the hospital can help him. He denies trying to kill Desmond but instead says that he was trying to show him something. Desmond wants to see his hand. Charlie realizes that Desmond must have seen something. Desmond asks "Who is Penny"? Charlie says he is not going to perform because none of "this" matters. As he leaves, Charlie says to stop worrying about him and to start looking for Penny.
Charlie rings Widmore to tell him about not having Charlie. Widmore is angry and tells Desmond that he can explain to Mrs Widmore what happened. At the Widmore mansion Charles asks whether Desmond has met Mrs Widmore before implying that she is a difficult person, but when Desmond introduces himself to Mrs. Widmore she is charming and says that its about time they met and that he should call her Eloise. Desmond explains what had happened and Eloise says that its OK and that her son will understand because employing rock stars means some unpredictability must come with the territory. When Desmond asks if she is angry, Eloise says "Not at all dear, what happened, happened".
As he leaves Desmond hears the name "Penny" read from a list of guests but when he tries to see the list Eloise intervenes sternly, and takes the list from him. She takes him aside and tells him to stop, that whatever it is that he thinks he is looking for he should stop looking for it. She says that he should not need to look for anything as he has the perfect life and has attained the thing he wanted more than anything, the approval of Charles Widmore. She adds that it is, in fact a violation. When he presses her about the list she says that he can't see the list because he is not ready yet.
At his limo, Desmond has a drink when a knock comes at his window. The man knows Desmond's name and introduces himself as Daniel Widmore and says they need to talk. Desmond starts to apologize for Charlie's absence but Daniel asks if he believes in love at first sight. Daniel tells of his love for a redhead who works at the museum. He says when he saw her it was as if he already loved her. He continues that that night he woke and wrote in his notebook. He shows Desmond the notebook entry and explains that a mathematician friend said that these were advanced quantum mechanics equations which would need a lifetime of study to understand. He tries to explain to Desmond that it is like something catastrophic was about to happen and the only way to stop it was to release a huge amount of energy, such as exploding a nuclear bomb. He rhetorically asks whether this life was not meant to be our life and that there was another "life" and for some reason "we changed things". He adds that he doesn't need to explode a bomb because he thinks he already has. Desmond says he doesn't know what this has to do with him. Daniel then asks why Desmond is looking for Penny. When Desmond says he doesn't know what he has found and that it is just an idea but Daniel tells him he knows and that what he found is love. When Desmond says he doesn't even know that this woman exists, Daniel says "No, she's my half sister" and he tells Desmond where to find her.
Penny is exercising in the stadium doing a tour de stade. Desmond watches and then approaches her and asks if she is Penny, introduces himself and offers his hand. Penny takes it and they shake hands.
Desmond revives and asks what happened. Penny explains that he fainted and that she must have quite an effect on him. He agrees. She asks if they have met before. Desmond invites Penny to coffee and they make plans to meet in a coffee shop in an hour. Desmond returns to the limousine. George, the driver asks Desmond whether he found what he was looking for and Desmond says he did. George asks if he can get Desmond anything else and Desmond asks for the passenger names from Flight 815 saying "I just need to show them something".
Original timeline (2007)
Desmond wakes up. Zoe introduces herself and explains that he has been unconscious for the last few days and that she has given him a shot to help him wake. Desmond calls out that he wants Penny. Charles Widmore says that that will not be possible. Widmore reminds Desmond that he was shot by Benjamin Linus.
Desmond calls for Penny again but Widmore says she is not here but that she and their son are perfectly safe. Widmore says he didn't have a chance to explain but even if he had Desmond would not have come. When Widmore tries to explain that he has brought him back to the Island, Desmond attacks Widmore and has to be restrained. He screams to take him back but Widmore says that he cannot because "the Island is not done with you yet".
Widmore leaves the room. Outside the room, Jin has been watching and he asks what Desmond is doing on the Island. Widmore says he will show Jin and tells Zoe to bring Jin to the generator room where they can start the test. Zoe protests that the test is not scheduled yet but Widmore insists and says to get it ready now.
As Zoe leads Jin outside they pass generators and capacitor equipment and major cabling as well as one large central piece of equipment shaped like a cube. Upstairs in the control room of the Hydra Station preparations are underway with laptops, monitors and electrical controls. Seamus says to Zoe that they aren't even close to being ready. They turn the generator to full for a power test, but shortly the circuit fails. Seamus sends Simmons to check the circuit on the solenoids in the central structure outside. Seamus tells the white rabbit, Angstrom that he is going in there next.
Simmons goes into the outside unit but in the control room a technician finds the fault and immediately throws a switch to re-power the solenoids. They realize that Simmons is inside and he is engulfed in shock waves generated by the solenoids. Seamus and Zoe run down to the main box and find Simmons smoking and dead, his face charred. Widmore arrives and asks Zoe whether they are ready as Desmond is dragged, struggling, in. He looks aghast at the dead man.
The dead man is taken out and Widmore looks sadly at his face but orders Desmond to be taken inside. He says to Desmond that if what he has heard about him is true then he will be fine. Desmond is tied to a chair between the solenoids. Widmore tells Desmond that once the experiment is over he will ask Desmond to make a sacrifice. Desmond asks why would he do that. Widmore tell him that his son died here for the sake of the Island, that Penny hates him and that he hasn't even met his grandson. He adds that if Desmond won't help, it will all be for nothing as everyone will be gone forever. Desmond is locked in the solenoid chamber room.
In the control room Jin demands to know what is happening and Widmore explains that Desmond is the only person known to have survived a catastrophic electromagnetic event and that he needs to know that Desmond can do it again "or we all die". He orders the experiment to be turned on. The closed circuit vision show Desmond free of his binds frantically trying to escape from the room. Widmore pulls the switches to start the solenoids himself. Desmond is engulfed by the flux.
Seamus and the other technicians go into the chamber and find Desmond alive. Widmore asks him how he is and when Desmond asks he tells him he was unconscious for just a few seconds. Widmore says his talent is vital to the mission and offers to explain. Desmond interrupts to say he understands and he is ready to start doing whatever it is that is so important.
Zoe and two others are escorting Desmond. Desmond explains his cooperativeness by saying a lot can happen in twenty minutes. Sayid leaps out of the bushes, flattens the two escorts and points a gun at Zoe telling her to run. She runs off. Sayid says to Desmond that "these people are extremely dangerous" and that he and Desmond need to go now. Desmond says "Of course, lead the way".