Catching Up With The Daria Gang was a 2017 online article for Entertainment Weekly, written by Susie Lewis and art by Karen Disher, for the 20th anniversary of the show. It showed how Lewis and Disher thought the characters would be in 2017.
Lewis said she'd had the characters in her thoughts for a while after the show ended.
- DARIA: "The sardonic teen has left the suburbs of Lawndale for New York City’s Hell’s Kitchen (naturally), where she’s grown up to become the only female writer on a late-night talk show. She lives alone — except for her black cat named Godzilla, who is toilet-trained, thanks to Daria’s hard work and dedication — and while she’s tried the online dating game, she hasn’t found anyone special quite yet. Oh, and in case you were wondering, she’s gotten past her crush on Trent."
- HELEN AND JAKE: "Daria and Quinn’s parents are living it up as retirees. Every time Daria speaks to them, they’re venturing out on yet another cruise, but whenever they’re back in Lawndale, they’re breaking a sweat in their weekly dance class."
- TRENT: "While his Mystik Spiral days are over, Trent has found, well, not success exactly, but… a functioning band in Trent Lane and the Mystikal Explosion. He lives with his four bandmates in Queens. Trent had some financial success with Mystik Spiral’s one-hit wonder, “Freakin’ Friends,” but since then has been making ends meet as a bartender. He and Jane still spend a lot of time together, and Daria often joins in. (See? It’s not weird anymore, guys.)"
- JANE: "Daria’s closest friend and confidante never gave up on her ambitions: She’s a professional artist who’s sold a few pieces, though she still hasn’t “made it big.” She lives in a loft in SoHo with her husband who’s an archaeologist and rarely home, so luckily the besties get to spend tons of time together. They enjoy going to art shows and film events where you’re supposed to socialize, but — surprise! — they only talk to each other."
- QUINN: "The younger sister of Daria has consciously uncoupled from her college sweetheart and dropped her last name. (Rumor has it that once Quinn realized his athletic abilities weren’t going to cut it professionally, she was done.) Quinn has triplet sons — Timmy, Tommy, and Teddy — and she still lives in Lawndale. In between caring for her boys and her hair extensions, she’s hard at work on her popular YouTube channel dedicated to dessert and skin care called “S’mores and Pores.”"
- KEVIN AND BRITTANY: "The head cheerleader and quarterback of Lawndale High are married and have three girls and two boys. Brittany is the weathergirl at the local news station and moonlights as part-time cheerleading coach at Lawndale High. Kevin is a stay-at-home dad who dabbles in children’s birthday-party entertainment. While he can’t quite squeeze into his belly-baring uniform anymore, you better believe Brittany’s cheerleading uniform fits her like a glove — and she wears it every Halloween."
Links to other speculation
Tracy Grandstaff had said in 2010 she hoped Daria contributed to either the Huffington Post "or The Colbert Report" - and Glenn Eichler did contribute to the Colbert Report. The inspiration for Daria's job here would seem to be her show's co-creator, Eichler.
- The show implicitly decides Daria went to Lawndale in 1997, when the show started. This clashes with numerous parts of the canon but every chosen timeframe for the show clashes with bits of the canon! There are no rules! Anarchy!
- Karen Disher would've also overseen the future versions of the Morgendorffers in "Write Where It Hurts", which is how Daria presumes/wants herself and her family to look like. The versions Disher draws here are not like those ones, though Daria was right that she'll still be wearing drab colour unfashionable-but-comfortable clothes.
- Jodie, Mack, Tom Sloane, and any of the teachers are noticeable by their absence.
- The characters in their 30s actually have more lines under their eyes and general wrinkles than Jake and Helen did in the show, where they're in their mid-to-late 40s. This would be to make it clear the characters were twenty years older than their original models.
- Glenn Eichler's "What I Think About Valentine's Day" said Daria had a boyfriend. With Daria specified as living "alone", it seems that relationship ended.
- Brittany was clearly planning to break up with Kevin when she was going off to college and he was repeating his last year at school, back in "Is It College Yet?" It's not said if they got back together later or if she changed her mind.
- Quinn got divorced after having triplets? That suggests a big issue with the marriage! (Roentgen theorised the problem was that when the husband finally 'washed out' and not scrambling for sports positions, they were around each other a lot more than they used to be and that made it clear the relationship wasn't working out.)
Two-Eyed Charlie wrote a lengthy story using the 'new canon', "The More Things Change", where Daria is having a terrible time as the only female writer on the show and is in a deep depression over how she has achieved her goal of being a writer, only to find it makes her unhappy.