Back in his office, Matt's pestering the hell out of Cal about this Tim Batale thing. He apparently "always" wore a blue Oxford shirt and tan khakis. Cal's like, "That's what everybody wears," which is a fine point in general, though if the writers' room was always as slovenly as we've seen, I kind of doubt that it's true in this specific instance. Cal finally snaps at Matt that he doesn't remember the guy, but that he needs Matt to help him with the effing big board already. In particular, they're talking about moving "Singing Teacher" around, so we know Luke's sketch has had a long and productive life on the show, even under Matt's regime. Wait, is Luke Scott an anagram for Matt Albie, too? Lemme check...wait...no I guess not. It is an anagram for "Tuck Stole," however, so be on the lookout for that guy. While I work out more anagrams in my head ("Suck T. Leto?"), Matt travels back to 1999.
The transition is pretty cool this time, as 2007 Matt tapping his hand to his forehead is blended with the sound of 1999 Matt knocking on Harriet's dressing room door. They banter cutely for a minute, before Matt jumps right into a discussion on "angels," because if there's anything I appreciate after some douchebag offends my belief system, it's when he comes back to try and argue the merits and explain to me exactly why I'm an idiot. He gets Harriet to say that she believes there are angels numbering 100 million, because that's what the Bible tells her. Matt's all, "A-ha! You mean in Revelations [sic] verse whatever-whatever-I-obviously-researched-this-so-I-could-better-show-you-up where they say '10,000 times 10,000'? Doesn't that just mean the people who wrote the Bible were stupid and couldn't count properly?" Harriet offers the reasonable-enough explanation that "10,000 times 10,000 is more poetic," but it makes Matt feel better to figure that they were just stupid. Having sufficiently buttered her up, Matt says that he has another idea for a sketch. Harriet says that Luke already pitched her a pretty good sketch. She doesn't add, "And he managed not to call me a dipshit in the process," but I like to think it's implied. Matt's idea also involves Harriet playing a teacher, interestingly enough, but this time it's Brandi Chastain as a math teacher. "Who's Brandi Chastian?" Harriet asks, and I'm so glad she did. Matt pulls down the "It's 1999!" flow-chart and explains that, in this year, 1999, the U.S. women's soccer team was a big deal for a few months there, and Brandi Chastain kicked the goal that won them the World Cup, and then she ripped off her shirt. So Matt's bright idea is for Harry to play Brandi teaching Social Studies, and every time someone gets a question right, she rips off her shirt. Harriet notes that it's essentially a one-joke premise. Matt apologizes for being a doofus, and Harriet clearly finds him to be cute. Harriet then tells Matt that she read his two one-act plays. She says that he's funny in a wordy way (half right); why is he trying to impress her with "physical comedy"? "What makes you think I want to impress you?" asks Matt. "Why'd you read Revelation?" she counters. "Why'd you read my one-act plays?" he returns. She's caught, so she laughs if off, and he asks her to go grab something to eat with him. Harriet, however, has to go work on her sketch with Luke. Oof! Matt backs away, insincerely singing Luke's praises and promising that he'll work on something for Harriet that works. "There's not an ounce of quit in me!" he exclaims, pointing at her with both fingers. The camera pulls in on Harriet this time as she smiles at the dweeby but cute man. ("Well, he clearly despises everything I believe in and talks down to me about it. But he did want to see me with my shirt off...")