Happily Ever AfterDesmond wakes up in a DHARMA infirmary on Hydra Island, and learns from Charles Widmore that he's been brought back to the Island. He snaps and starts beating Widmore with an IV stand, demanding to be taken back to the mainland, but a pair of Nerd Herders wrestle him down and Widmore says that that Island isn't done with Desmond yet. Outside the infirmary, Widmore orders
Widmore: That man is the only person I'm aware of, in the world, who has survived a catastrophic electromagnetic event. I need to know that he can do it again, or we all die.The Nerd Herders switch on the generators and Widmore throws the switch himself. The generators begin to heat up and glow with an intense electromagnetic energy...
In LAX, Desmond is staring at the Oceanic Airlines arrival board when Hurley walks past and tells him their bags are at carousel 4. While retrieving his bag, Desmond helps Claire to get hers and walks her to the terminal, guessing that her baby will be a boy. He meets his limo driver, George Minkowski, outside and they head to "the office". George offers to find him some company but Desmond is here to work—after all, he's the boss' right-hand man. At the office, Desmond meets with his boss, Charles Widmore, and they greet one another like old friends. Later, Widmore asks Desmond to clear up a situation for him: a band called "DriveShaft" is supposed to play alongside Widmore's son at a charity event being hosted by Widmore's wife, but the bass player, Charlie Pace, was arrested for possession, and he wants Desmond to bail Charlie out and get him to the gig. To celebrate Desmond's "indispensability", Widmore offers him a glass of sixty-year-old Mac Cutcheon whiskey. Desmond meets Charlie and his lawyer outside the police station, but Charlie doesn't stay, instead marching right across the road (through heavy traffic) to a bar. They talk, and Charlie theorises that Desmond is unhappy because he's never been in real, "spectacular, consciousness-altering love" before.
Charlie: Do you know what that looks like?
Desmond: I wasn't aware that love looked like anything.
Charlie: I've seen it, mate. On the plane back from Sydney.
Desmond: Is that so? Well we were on the same flight, so maybe I saw it too.
Charlie: Trust me, you didn't.
Desmond: Oh? Enlighten me.
Charlie: There was this woman, two rows in front of me, in handcuffs, sitting with a cop. He looked at me, knew I was holding. If I didn't take action I'd be caught. So I got up, went to the lav, proceeded to eliminate the evidence by swallowing my stash. And at that exact moment we hit turbulence. I choked. The entire bag of heroin is stuck in my throat. It's over. Everything starts to go dark, I'm slipping into the abyss, and then I see... her. [...] A woman. Blonde, rapturously beautiful. And I know her. We're together. It's like we've always been and always will be. This feeling, this love, and just as I'm about to be engulfed by it, I open my eyes and this sodding idiot is standing there asking me if I'm okay. But I saw it, just for a moment, I saw what it looked like.As a result of his epiphany, Charlie doesn't care about going to the gig, but Desmond offers him a choice: stay in the bar and very likely destroy his music career, or go to the gig and get in Charles Widmore's good graces. Charlie comments that it "doesn't really seem like a choice." Driving to the gig, they're passing the LA marina when Charlie starts up again about how Desmond is really miserable because he's got nothing meaningful in his life. To demonstrate what he's talking about, Charlie grabs the wheel and steers the car into the marina. Desmond tries to pull Charlie out of the car, but when Charlie presses his palm against the glass window, Desmond has a flash of 'NOT PENNY'S BOAT' written of Charlie's hand as he drowns. It only lasts for a moment, and once the flash has passed, Desmond pulls Charlie out of the water. At the hospital, Desmond is examined by a doctor and taken for an MRI. As soon as the machine is turned on, he has another flash of Charlie drowning, and then a series of very rapid flashes of himself with a beautiful blonde woman he's never met before. He leaves the MRI machine and starts looking around the hospital for Charlie. The nurses won't help him, but Desmond recognises Jack and asks for his help note . Just then, Charlie sprints down the hall and Desmond gives chase: he corners Charlie in a room, demands to see his hands and asks who "Penny" is. Charlie realises that Desmond has seen something.
Desmond: All right, come on. We're leaving.
Charlie: Whoa! You think I'm going to play a rock concert after this? This doesn't matter. None of this matters. All that matters is that we felt it. You wanna try and stop me? Good luck.
Desmond: Hey, where you going?
Charlie: If I were you, I'd stop worrying about me and start looking for Penny.Charlie runs away and Desmond calls Widmore to update him on the situation. Very displeased, Widmore gives him the punishment of informing Mrs. Widmore. George drives Desmond to the Widmores' mansion, where Eloise Widmore is making last-minute preparations for the charity event. Despite her reputation as a dragon lady, Eloise isn't angry in the slightest when Desmond informs her that Drive Shaft can't perform. However, when Desmond hears the name "Penny Milton" being read off the guest list and inquires about it, Eloise gets angry and steps in.
Eloise: I want you to stop.
Desmond: Stop? Stop what?
Eloise: Someone has clearly affected the way you see things. This is a serious problem. It is, in fact, a violation. So whatever you’re doing, whatever it is you think you’re looking for, you need to stop looking for it.
Desmond: Do you know what I'm looking for, Mrs. Widmore?
Eloise: I don't know why you're looking for anything. You have the perfect life. On top of it, you’ve managed to attain the thing you wanted more than anything: my husband's approval.
Desmond: How do you know what I want?
Eloise: Because I bloody do!
Desmond: I need to see that list, or you need to tell me why I can't.
Eloise: You can't because you're not ready yet, Desmond.Desmond goes back to the car, where he is met by the Widmores' son, Daniel. Daniel describes a similar phenomenon to what Desmond and Charlie both experienced, brought on by seeing a beautiful, red-haired, blue-eyed woman in a museum and feeling like he'd been in love with her for years. What's more, after this experience he went home and wrote something in his notebook that seemed to be gibberish, but was actually complex quantum mechanics equations, equations that Daniel, being a musician, couldn't possibly have known.
Desmond: So what do they mean?
Daniel: Okay. Imagine, Imagine something terrible is about to happen. Something catastrophic, and the only way to stop it from happening is by releasing a huge amount of energy. Like setting off a nuclear bomb.
Desmond: You wanna set off a nuclear bomb.
Daniel: Just listen, what if this, all this, what if this wasn't supposed to be our life? What if we had some other life and for some reason, we changed things? I don't want to set off a nuclear bomb, Mr. Hume. I think I already did.Daniel is explaining all this because he knows what's happened to Desmond, and what's more, he knows who Penny is: she is Daniel's half-sister. Desmond follows Daniel's directions to the LA stadium and finds Penny doing a stadium run. He goes up to her, nervously introduces himself, and they shake hands.
Seconds after the generator was turned on, an extremely zen-like Desmond wakes up in the giant box on Hydra Island and looks down at his hand. Zoe and Widmore enter and find that Desmond is perfectly fine.
Widmore: I'm really sorry we had to do this to you, Desmond. But, as I told you, your talent is vital to our mission. So, if you just let me explain—
Desmond: It's all right. I understand.
Desmond: I said, I understand.
Desmond: You told me you brought me here to the island to do something very important.
Desmond: When do we start?Zoe and a pair of Nerd Herders are taking Desmond back to the Hydra Island infirmary when Sayid shows up, kills the Nerd Herders and tells Zoe to run. He starts trying to convince Desmond to come along, but Desmond (still very zen-like) tells Sayid to lead the way.
Desmond comes to in the stadium. Despite the embarrassing circumstances, he and Penny hit it off and agree to meet for coffee later before Desmond returns to his limo.
George: So, did you find what you were looking for?
Desmond: Yes, George, I did. Corner of Melrose and Sweetzer, please.
George: You got it. And if there's anything else I can do for you, Mr. Hume, you just name it.
Desmond: Actually, there is one thing, George. Can you get me the manifest for my fight from Sydney? Oceanic 815, just the names of the passengers.
George: Sure I can. Do you mind if I ask you what you need it for?
Desmond: I just need to show them something.