Hurley has a chat with Libby graveside. Ilana informs him that they're going to the Black Rock and asks who he's talking to. Sads. And then Michael shows up to stop him from killing people (Hai Mikey!).
When Ilana comes back with the dynamite, Hurley tries to convince her that blowing up the Aljira plane is a bad idea. She argues back that Jacob said to trust Richard and Richard says to blow up the plane, thus the right thing to do is blow up the plane. Clearly she forgets that she's got unstable dynamite sticks in her bag because she throws it around and BOOM goes the dynamite and BYE goes Ilana into itty-bitty Ilana bits.
The rest trek to the Black Rock supposedly to get more dynamite only Hurley blows up the ship to protect them. Talking to Miles, Hurley mentions how dead people come and yell at him because "dead people are more reliable than alive people."
Richard and Hurley have a throw down and demand everyone take sides ala when Jack & Locke had the Losties take sides - one to go to New Otherton and one to the beach to meet the freighter people. Miles and Ben go with Richard to get grenades and such from New Otherton to blow up the plane. Jack, Sun and Frank go with Hurley to talk to Locke.
As they walk, Hurley admits to Jack that he didn't see Jacob and has no idea what he's doing. But Jack trusts him because somehow Jack trusts others now. The whispers come back and LIGHT BULB! Hurley knows what the whispers are. They're the souls of people trapped on the Island because they can't move on. Like Michael because he killed Ana Lucia and Libby he's not allowed peace. When Hurley asks if there's anything he can do, all he requests is that Hurley not die, and to tell Libby he's sorry if he sees her again. Oh Michael. Your redemption came too late.
Hurley walks into Camp MIB/UnLocke/Smokey and asks for a conversation sans weapons. MIB/UnLocke/Smokey agrees. Well he appears to agree because he handed over his knife. But we're talking about a creature that can turn into a pillar of smoke and wreak havoc on a group of people. I'm not entirely sure I would trust him at his word is all I'm saying.
Sawyer demands to know what MIB/UnLocke/Smokey is waiting for. Apparently it takes teamwork to do anything around the Island so they're waiting for the rest of the Losties to come to them. Sayid shows up and requests a private meeting with MIB/UnLocke/Smokey and shows him Desmond tied to a tree.
MIB/UnLocke/Smokey cuts Desmond free and asks him why Widmore brought him back to the Island. Desmond is a little evasive. And when MIB/UnLocke/Smokey asks him if Desmond knows who he is, he replies, "You're John Locke" Oh Desmond, brutha, you got a ways to catch up.
As Desmond follows MIB/UnLocke/Smokey into the jungle because he has something to show Desmond, they see the young boy that MIB/UnLocke/Smokey and Sawyer came across in the Sawyer episode. MIB/UnLocke/Smokey freaks out and demands Desmond just ignore him. The boy looks clearly pleased with how he's rattled MIB/UnLocke/Smokey and giggles as he runs off.
MIB/UnLocke/Smokey takes Desmond to a well. He gets shifty eyed and wonders aloud why Desmond is not afraid. Sir, Desmond laughs in the face of fear. BWAHAHAHA! Then MIB/UnLocke/Smokey throws him into the well. Oopsies. Slipped.
And when Hurley and his crew come walking into camp, MIB/UnLocke/Smokey looks smug as everything's going to plan.
Marvin Candle aka Pierre Chang introduces Hurley as some paleontology wing/school's man of the year. And as Hurley leaves with his mom holding yet another award, she laments on how everyone loves Hugo except women. She presses him to go on a blind date she set up. His mom is not any different in the Sideways world as she is in the Island world, wanting to see her boy find love.
Hurley waits in a Mexican restaurant seemingly stood up when Libby shows up. She asks if he believes in soulmates and because he felt an immediate connection to her she agrees. Libby gets escorted out of the restaurant by a doctor and loaded into a van for the Santa Rosa Mental Institute and Hurley's disappointed.
So he drowns his sorrows in a bucket of chicken at one of his Mr. Cluck's stores which is where Desmond runs into him on "accident" and tells him to trust his instinct and believe what Libby said about how they already knew each other.
Hurley stops by the Santa Rosa Mental Institute and asks to see Libby. She explains her memories of another life. Her Island life. Desperate to know that Hurley has the same memories because it would mean she's not crazy. Sads for Libby because he doesn't remember. But he does ask her out on a date so yays for that!
Hurley and Libby finally get their picnic date. And when she kisses him he gets flashes of his Island life and realizes that Libby was right. And Desmond who has been witnessing this whole exchange drives off satisfied that one of the Losties knows the truth, or part of it, of the Sideways world.
Flash Sideways Coda
Desmond watches John Locke roll through the parking lot at the high school. After being interrogated by Ben because who wouldn't be wary of a strange man parked for a period of time at a school staring at children, he speeds off directly for John Locke and runs him the eff over. Why? Probably because he's supposed to be dead, my guess.