Personally, I didn't like Tom. He was fine every now and then as Jane's boyfriend, but once he started dating Daria, he was around too much. Obviously it made sense since they were dating, but the more he was around, the less I could stand him.
I would've preferred if they did his whole arc in just one season (date Jane, switch to Daria, go away for good).

I think Daria is relatable no matter what decade it is in. I was in year 7 in 1997 when I first saw Daria so I understood the culture references but over all the situations are in every decade.

Considering that this is a cartoon and a bit exaggerated (as cartons are) this really is a pretty accurate depiction of high school life at that time. I graduated in 1996 and watching this show makes me feel downright weird at points because it takes me back to those years.
"Why couldn't the monkey arrange this from INSIDE the garbage can?"

True ! They did get real there !! I always thought Daria was pretty much on point with highschool life ( well I think anyways, I wasn't really in highschool until 2000 ) but it always seemed correct for the most part

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