Apartment. Ted, Robin, Marshall and Lily are going through all the designer clothes. Ted wonders if Lily's worn half of this stuff. Robin says she's sure Ted has something in his closet he hasn't worn. Annoyingly, he says, "Uh... as a matter of fact, there isn't." "Whatever, red cowboy boots!" Robin announces. Ted says those boots are nice and he can pull them off. Marshall asks Lily, who's coming in from another room, what article of clothing that Ted owns can he not pull off. She knows it's the red cowboy boots. Ted says it's a classic western look. Writers, start your gay cowboy joke engines. Robin: "The Good, The Bad and the Fabulous." Lily: "The Magnificent Kevin." Marshall: "No Country for Straight Men." Lily moans about not wanting to sell her clothes. Robin hugs her. She admires Lily's vest and asks if it's 100 percent silk. Marshall says they really need the money and until he gets his next job, he doesn't know what else to do. Lily offers to sell her paintings. Marshall: "What?" Lily says a good oil painting sells for about $500. SagetTed breaks in to remind the kids about how you can do something right 1,000 times, but screw it up that 1001st time. Montage of Marshall telling Lily that her paintings are, "A masterpiece," worth staring at instead of the TV and museum-worthy. This time, though, he says, "That kind of money only goes for real paintings. Uh oh." Lily, hurt, asks what that means. Marshall explains that they need the money fast, and he doesn't know if her stuff will sell. "You don't believe in me!" she says. Lily says she's proud of her work and that her paintings are good. She thinks Robin would buy one. "What now?" Robin asks. She's luxuriating in Lily's clothes. Marshall says he's just trying to be realistic. He says they need $1,500 for the repairs. Honestly, for a nice New York City apartment, that doesn't sound like much. That's like, what, half of one month's mortgage? Lily thinks she can sell three paintings for $500 each and keep all her clothes. Robin looks guilty holding one of Lily's dresses. Marshall agrees reluctantly to give Lily a week. Spaghetti western music starts to play as Ted strides out from his bedroom. He puts a boot up on the coffee table. It's a ridiculously bright set of red cowboy boots. They look like galoshes. And his jeans are tucked in. Wow. Please do not come to Texas with those things, Ted. "Pulling. Them. Off," he says, confidently. Please do pull them off of your feet.
We return from commercials to see Lily standing in an art gallery. SagetTed says that Lily was accepting the Art Challenge of 2008 by displaying her painting in a friend's art gallery. Lily, wearing a weird tuxedo front blouse is standing in front of her piece, which has tons of bright colors and is surrounded by a huge, thick frame. People pass by her painting and don't give it a glance. A song called "The Painter" by I'm From Barcelona plays as the scene goes into fast motion. Either that or people really want to get away from Lily's painting as fast as possible. A woman finally stops in front of Lily. She's got gray hair and glasses. "I love it," she says. She looks rich, too. "You do?" she asks. The woman loves Lily's top and asks if it's 100 percent silk. "It's not for sale, my clothes are not for sale!" Lily yells, driving the lady off. Cut to the next day as Lily is showing off her painting in a coffee house that displays art. Nobody's looking. She sits between Ted and Robin. Lily asks them to talk it up. Robin says nice things about the painting, all of them using the word "Neat." Ted says "Observe" and clears his throat. He gets all Know-it-all-Ted about the artwork, talking about the brushwork and the composition. He goes over the top with "an almost Kandinsky-like emotional resonance." Robin says you can enjoy it even if you're not a pretentious douche. Ted asks Robin if the colors are "Neat" or "Neato burrito." "Then again, red cowboy boots," she says. Ted is wearing them and has his feet propped up. "I pull these off!" he says. The coffee house titters in disagreement. Ted has the yell I tout again. Keep believin', dude.