Daria Morgendorffer and Jane Lane had been friends for nearly sixteen years, facing various hardships and vast amounts of chaos, but always coming out on top. There's something about wit and sarcasm that just clicks. Throughout college and beyond, they had been roommates. They now lived in New York in a spacious condo paid for by hope and fear – or, rather, their mediums of expression. Daria was a regular blogger for The Huffington Post, sharing her cynicism with the rest of the world; Jane was fulfilling her dream of starving artistry (only, without the money problems).

In their second year of college at their respective schools in Boston, Daria and Jane were approached by Jane's then boyfriend (and only Jane's boyfriend), Tad, who was a broadcasting student at Raft, working for the student-operated campus television station. He had said something about "insight," "snark," and "wit," and the potential that these things had for great TV – at least in the eyes of college students. It took plenty of convincing by Jane, but eventually she and Daria agreed to do the show. It was a half hour segment of Jane and Daria talking about world issues, philosophies, art, and stupidity; it required little effort on the part of either female. To their astonishment, and Daria's in particular, it became quite a hit on campus. As in high school, they became moderately popular despite their years of mocking the "popular kids."

A local Boston television station that was on the look-out for entertainment that would draw in the "younger crowd" got wind of the show and offered the girls a paid spot on their station. Daria certainly had no desire for the change in scenery, but, again, Jane convinced her. Jane's success was based on the lack of money in each girl's pockets and their shared desire to move into an apartment instead of remaining in the crowded dorms on their respective campuses. The ratings for their show were high, even with the older crowds, delighting the small station. But after one short, ten-episode season, the show was cancelled. New management with strong religious ideals took over the station and gave it a make-over, which meant happiness was in and reality was out. Despite Daria and Jane's short TV careers, they made a healthy amount of money, which they saved for the summer when classes were out and living quarters were lost.

Instead of moving everything back to Lawndale to overbearing parents (in the case of Daria, anyway) once college was out, they rented a small two-bedroom apartment in the rough part of Boston. Over summer, Daria worked on her writing, continuing to earn a little money through short stories that were published in digests, magazines, and anthologies. She also acquired a summer job working in a used book store. It worked well for her; she could read and work on her writing, and not worry about interacting with many people.

Jane continuously worked on her art, enough for Tad to eventually break it off; this gave Jane inspiration for a series of paintings that were a strange mix of "funny" and "horrifying" (according to critics). This series, which she called "A Tad Troubled," was featured at BFAC's August art show, earning her recognition, not only by her fellow art students and her professors, but also from Boston's art community as a whole. A husband and wife who owned the Leighton Art Gallery in downtown Boston saw her paintings and insisted that she put on a weekend showcase while offering said paintings for sale. The couple further insisted that she sell them for no lower than one-thousand dollars; Jane had little hope for them selling at all, so agreed to the inflated prices. There were fifteen paintings in the series and, by Sunday night, ten of them had sold, earning Jane just under twenty-thousand dollars. The Gallery bought one of the unsold paintings for another three-thousand dollars to put on display in their "Talent Unheard" section. By the end of the month, just in time for Daria's and Jane's third semester, the rest of Jane's paintings had sold. For some reason that was unfathomable to Jane, though she didn't complain, she had earned nearly forty-thousand dollars. She had also made a name for herself in the art world, at least in Massachusetts and its surrounding areas. Various people told her that she could still be successful without finishing her degree and should just focus on her art, but with one year remaining, it made much more sense to simply finish. Plus, she would be the first "outcast" Lane to actually earn a post-secondary degree and there was a certain amount of pride that went along with that notion.

Upon Jane's graduation, Daria decided, against all better judgement, that she would throw Jane a graduation party. It would be an "I hate people, but I like you, and you like parties" party, and Jane would understand the sentiment. Her graduation day was in the middle of May, and it was a lovely day – a "perfect day for scholastic achievement," as described by Jane. To her surprise, her immediate Lane family showed up in whole, along with Summer's kids. Trent had arrived with Jesse and was therefore free to sit from the chaos that became the Lanes when they were together; instead he sat with Daria and her family. The Morgendorffers showed up as well, much to Daria's chagrin, though to Jane's delight.

The ceremony was rather uneventful. The class was rather large, so the wait for Jane was long and tiresome, and the body heat of hundreds of people in one great room caused time to drag. When the ceremony ended, everyone rushed to get into open air and greet the graduate. Her parents gushed and hugged her, which was something she was not use to in the slightest, and the rest of the Lanes congratulated her achievement. It was very "1980s sitcom." Then the Lanes, save for Trent, went their separate ways. The Morgendorffers congratulated her as well; Daria had to save Jane from the congratulatory praises, Boston fashion tips, and judgement that was spouted from Quinn. Jake and Helen made their way back to the hotel in which they would spend their weekend before heading back to Lawndale. Quinn tagged along with Daria, Jane, Trent, and Jesse who went back to Daria and Jane's apartment so that shenanigans could ensue.