She shrugs off his refusal, saying it's only four dollars, and he "jokingly" asks if she's got $42,000 more. I think the last thing I'd want from some bounder whose coffee I'd paid for would be some sort of sob-story pitch, but Libby sits down with Desmond, and he tells her about the round-the-world sailing race he wants to take part in. It's not so much the prize as who he'd win it from: Charles Widmore, AKA Old Bastard. And he tells her about Widmore trying to buy Desmond off, and keep him away from the most important thing to him in the world, and Libby brilliantly deduces this is about a woman, and the $42,000 is because he doesn't have a boat just yet. But guess what? Libby has a boat, and Desmond can have it! Just like that! Yes, just that quickly. The boat was her husband's, who got sick and died just a month ago, and he named it after her, and she gives it to him! She gives the boat to a stranger who couldn't pay for his own coffee! "He'd want you to," she says, when a shocked Desmond protests. Okay, this is the first we've heard of Libby's husband, so I don't know anything about the guy? But I know HE WOULD NOT WANT HIS WIDOW TO GIVE A STRANGER THE BOAT HE NAMED AFTER HER. Desmond asks what her husband's name was. It was David. You can't tell me that it's a coincidence that Libby's former asylum-mate Hurley's hallucination is named Dave (although I'm guessing that at this time in the flashback Libby hasn't gone nuts yet). So anyway, Desmond accepts the boat. Can't say I blame him, because hey, free boat, right? Desmond says he's going to win this race "for love," and then I throw up in my mouth a little. On the other hand, knowing that the boat is named after Libby makes the on-board drinking a little more understandable.
On Craphole Island, Sayid's chatting with Sun, and Jin strolls up after checking on the little fire he's got going. Sun asks Sayid to excuse them, and then tells Jin Sayid's wants him to help sail the Elizabeth to the other side of the island to help Michael. I think that last part is supposed to help sell the loyal Jin on the idea, but he says no anyway, because he's not willing to leave his pregnant wife. This is because he's new at this. By the time she's seven or eight months along and angry at him for her new giant belly and waddle, he'll use any excuse to grab the car keys and run some errands. Trust me on this one.