Note: Desmond Hume's flashbacks are presented here in the order they happened in his life, as opposed to the order in which they were shown on the show. To read the flashbacks in the order they were presented to Lost viewers, see Desmond's profile for links to episodes containing his flashbacks.

Goodbye Kelvin

Episode 2x23, Live Together, Die Alone - Flashback 7
Desmond rinses his face in the hatch bathroom and Kelvin says, "You've been shaving every day for the last three years.

You need to live a little, let go."
"I'm never going to let go, brother," Desmond says as he looks at the photo of he and Penny on the mirror.

"Well that's the spirit." Kelvin zips his yellow suit. "Bye, Des."

"Goodbye?"

"Yeah, goodbye. See you in a couple hours."

Desmond notices a rip in Kelvin's suit. He puts a bandana over his mouth and follows Kelvin out of the hatch. He sees Kelvin take off the mask and yellow suit. He takes off the bandana and breaths deeply.

Desmond follows Kelvin across some rocks by the beach. Desmond sees his sailboat in the water.

"Well gosh," Kelvin says from behind Desmond, "I didn't think you had the stones to come after me. I was a spook for ten years, Desmond, I know when I'm being followed."

"What are you doing with my boat?"

"I'm fixing it."

"You were leaving?"

"Well, not yet, I'm still about a week away. You wrecked her pretty good, Des. So what do you think? Want to come with me?"

"Come where? What about the button?"

"Screw the button, man. Who knows if it's even real?"

"That's not what you said when you were going on and on about dams and electromagnetics and failsafes."

"Well, I was drunk," Kelvin says.

"Why did you lie to me!?"

"I lied to you because I needed a sucker to save the world after I left."

"You crazy old bastard." Desmond attacks Kelvin.

"Oh, come on." Kelvin laughs.

"You stole my life! What else did you lie to me about? What else? Tell me!"

They wrestle around on the rocks and Kelvin hits the back of his head and dies. Desmond is upset. He takes the keys from around Kelvin's neck and runs as fast as he can back to the hatch.

The timer is going off. A voice says, "System Failure" over and over again. The whole hatch is shaking. The timer has hieroglyphics. Things start flying around, attracted to the magnet. Desmond tries several times to type in the numbers and the computer finally accepts them."

A Letter from Penny

Episode 2x23, Live Together, Die Alone - Flashback 8
Desmond looks at his gun and takes a swig of booze. He pulls out his book and opens it. A letter falls out. It's from Penny.

Dearest Des,
I'm writing this letter to you as you leave for prison, and I've hidden it in the one place you would turn to in a moment of great desperation. I know you go away with the weight of what happened on your shoulders, and I know that the only person who can ever take it off is you.
Please don't give up, Des, because the only thing we really need to survive is one person who loves us and you have her. I will wait for you always.

I love you, Pen.

Desmond holds the letter and cries. "It's gone," he says and throws the booze. "It's all gone!" He tears apart the book shelves and falls to the floor. Then he hears banging.

Outside the hatch, Locke is yelling. Desmond looks up and shines a light. Then he smiles.