This is an Author's Note for Chapter 2, so you should probably read that for this to make any sense!
This chapter is set a year before TS1. In the original game, Michael Bachelor was a young man just out of college. 25 years later he died of "old age" at the age of -at most- 50, but that was Maxis's error when they decided to make him Bella's dead older brother. (Though really, there are no actual errors with the premade character's ages, everyone was just chugging the Elixir of Life. ^_~) TS3 really confused things up by making him a teenager 25 years before TS1, but I'm favoring the original, because it's nearly impossible to reconcile TS3 with the rest of canon, anyway.
So what about Dina? She's supposed to be waaayyy younger than him, and if this is 26 years before, shouldn't she be a little kid? Or if she's a teen, shouldn't he be middle-aged? Well, here's the thing: I don't have a problem with large age gaps if both people are adults, but it's a very different situation when teenagers are involved, even when the teenager is above the age of consent. Here's a screencap from the original Dina's memories (Labelled correctly, I promise. You can check it yourself.):
Here we see it is totally canon that Michael Bachelor kissed her as a teen. I just decided to make it an 18-year-old when he was within range of the "half your age + 7 rule", rather than something more disturbing. Since age is very weird and flexible in the Sims universe, I decided that Dina of Pleasantview is a little older than she looks, closer to Jenny Smith's age than Cassandra Goth's. (I know her lifetime bar says different, but this is a world of aliens, magic, cowplants, and age-altering drugs.) This way I could write about her canon first kiss in a way that didn't carry so many unfortunate implications.
So, in the future, why is Dina still young and hot when Michael is old and dead? You could ask the same thing about Bella and Mortimer. I have an explanation for both. I'm not throwing canon out the window, just working with its contradictions. I will try to make sure this prequel is building up to the Pleasantview of TS2; it just may not be in a way you'd expect.
As for The Sims 3, I'm not ignoring it (Hello, Parker Langerak.) I just think things would make a lot more sense if it was around 10 years prior to TS1 instead of 25.
Yes, I have thought about this all way too much. But I'm sure some other people have too, so feel free to let your geekiness run rampant in the comments!