Helen and Jake reunite with the Yeagers, friends from their hippie years that are still living the lifestyle twenty-five years later. Meanwhile, Daria and Jane help Trent sell vinyl records at the flea market, and Quinn pursues the Yeagars' son Ethan.
The Morgendorffers prepare to receive a couple of old friends for the weekend, Willow and Coyote Yeager, who are still living according to the old hippie subculture. Having shared their counterculture ideals back in the day, Helen is eager to make a good impression. Daria is uneasy around the guests and sneaks off to the Lane’s, bribing her sister to keep the guests company. Quinn, initially reluctant to stay, changes her mind with the appearance the Yeagers' son Ethan.
At the Morgendorffers, the adults reminisce about old times, talking about the time spent in the youth in a commune. At the same time, the Yeagers show bafflement at the Morgendorffers' more modern lifestyle and aggressive attitude, in contrast to the Yeagers’ still mellow habits: they make a living of selling hemp products, are vegetarians and put no pressure on their son to succeed athletically. Their comments and presence make Helen and Jake feel uneasy and guilty that they've given up on their youthful ideals and have sold out.
At the Lane’s, Trent Lane and Jesse Moreno excitedly play old vinyl records, in preparation to sell them at a local flea market the next day (at one point talking about the irreplacable warmth of vinyl while actually hearing the radio). The two young men recruit Jane and Daria to come along. Jane enthusiastically agrees, again playing yenta to her embarrassed friend. Daria uses this plans to stay the night at Jane’s, despite her mother’s initial objections. They all leave early the next day and occupy an empty cubicle in the flea market to display the records. Both young men quickly fall asleep, having stayed up all night to make sure to be up at six a.m.
At the next day at the Morgendorffers, Helen and Jake have felt their friend’s comments and try to compensate, with Jake growing a beard ("goodbye to cookie-cutter corporate guy Jake") and Helen reluctantly cooking breakfast. As the day goes on, however, both Coyote and Willow slowly reveal frustration with their lifestyle, including having to keep repairing their old car, wasting time kneading bread, poor hygiene habits and having to buy food in bulk. The Morgendorffers are then in a position to help: helping them get into the middle-class sellout culture they desperately want to experience.
Meanwhile, at the Lanes' cubicle in the Flea Market, business is going slow until Upchuck visits and charms his way into becoming a salesman. As he stays long enough to sell some records, Jane leaves him in charge while the rest of the party go for a snack: Daria and Trent eat at the food court and comment on the Yeagers’ hippie lifestyle; Jane offers some views on consumerism to an apparently oblivious Jesse as both get sodas. Returning to the booth, they have an unpleasant surprise of finding it ransacked: Upchuck had abandoned it while he and Anthony DeMartino searched through vintage porn mags.
Quinn, for her part, has spent the weekend chasing Ethan, who has ignored her and actively isolates himself and barely talks to anyone. He only begins showing more signs of life after scolding his father for drinking fermented berry juice. He later takes Quinn out for a snack and reveals some past secrets of both their parent’s youth. This is later used by the teenagers to escape punishment when Quinn, Daria and Ethan arrive late that evening.
The Yeagers leave the following morning, happy and thanking the Morgendorffers for their help. Quinn laments her lack of success with Ethan while Jake wonders about the need to keep up with times, concluding it is useless to stay stuck in the past and so he's going to get rid of all his records. "Hey, Daria! You want 'em?"
- The Morgendorffers haven't seen the Yeagers in twenty-five years, which at the time would have been 1973, and implies this is when they drifted away from being hippie. However, The Daria Diaries, also written by Bernstein, had shown the Morgendorffers were still hippies at their wedding in 1975—it's possible "it was time for us to move on" refers to the group house and not the lifestyle.
- The episode's title is derived from the novel That Was Then, This Is Now by S.E. Hinton.
- Anne Bernstein has said that in this episode, "Trent did catch on that Daria had a thing for him (see the open eyes in That Was Then)." 
- Upchuck is searching for a set of "fast food premiums" (the little toys you get free), something Anne D. Bernstein introduced in The Daria Diaries.
- An explicit date is established: Helen and Jake were at Boulder in August 1969, where they spent a night in jail after Helen punched a cop. Willow and Coyote knew them then, so they presumably went to Middleton College too, as the contemporary The Daria Database says Jake and Helen are part of the Class of '72. (See Datedness of Daria)
- When living in the hippy "group house," Helen and Willow had to do all the house work until Helen twigged this was just like in regular society.
- Jake, Helen, and the Yeagers once tried to levitate the Pentagon. This is a reference to a real-life "attempt" to do this in October 1967 by Abbie Hoffman and Allen Ginsberg during an anti-war march that was prevented from reaching the building, though the characters aren't part of a larger protest in this flashback. (This is the same march where George Harris famously placed a carnation in a soldier's gun) Whereas Hoffman and Ginsberg were doing guerrilla theater, young Jake actually believes it could be levitated...
- This is the only episode prior to Through a Lens Darkly that shows just how bad Daria's eyesight is when she's not wearing her glasses.
- While discussing "Zappa digital" and "Zappa analog," Trent and Jesse are listening The Mothers of Invention's album Weasels Ripped My Flesh.