Timothy O'Neill, unknown to Daria, enters her essay, "My So-Called Angst," into a contest to "Win a Day With Val," the vapid editor of the equally vapid Val Magazine. Daria is less than enthused, as she believes Val is essentially a narcissistic opportunist making money off the confusion of teenagers and foisting her own shallow beliefs on them (cos Val is); Jane, however, convinces her to go along with it, saying that the experience could be an opportunity to snag a trip to New York City.
They first meet (and Val winces when she sees Quinn's not Daria after all) at Daria's house, where Val stays for dinner and Jake hopes she explain to him what "edgy" is so he can sell it to his clients. Daria's initial biting sarcasm, where she boils down 'edgy' to "[a] fake concept of seeming to be dangerous when every move they make is the result of market research and a corporate master plan", seems to go over Val's head - Helen pleads with her to not be negative. ("I'm not being negative, I'm being edgy.")
At school, which has 'coincidentally' decided to have a Color Day on the same day Val will be around, Daria endures Val's incessant chatter, openly fake claims, and over-the-top efforts to fit in with the youth culture she supposedly represents. (Val, for her part, endures the fact she's got to follow Daria around and not a more popular girl as she hoped for - at one point forgetting who Daria is.)
Finally, Daria can take no more, and essentially tells her that she should "stop embracing the teen within and start embracing the 30-something without," grow up, and start doing more to help today's youth with their problems instead of adding to them. Enraged, Val leaves and, upon returning to New York, writes an article for Val about "today's underground bummer culture"... with Daria as the "anonymous" subject of the article. However, Daria isn't bothered by it. She's cool with it or "jiggy with it."
- The episode is ripping the piss out of Jane Pratt and her self-titled magazine Jane Magazine. Pratt herself was a good sport about it and in 2010 contributed a tongue-in cheek question, "would you parody someone now in order to make a social statement?", to a Tracy Grandstaff interview. In 1999, MTV's episode guides called it "a "Savvy" - like teen magazine" as a cover. The later website feature "Guestward Ho!" nodded to the real source: "Reminiscent of a real-life editor who named a magazine and a talk show after herself. (But her name has four letters, so it's so totally not her!)"
- The title of the episode is a play on the title of the 1987 film The Lost Boys, while the title of Daria's essay is a play on the title of the television series My So-Called Life.