I've loaded and reloaded Pleasantview many times in my course of playing, and there are a few things that generally always happen, but then sometimes I try to mix it up a bit:
Goths: Mortimer I have never married to Dina, he married Nina once which was surprisingly a good match and she actually fell head over heels for him, wanting to get married and have his babies etc (which was surprising for a romance sim) Usually though he gets a hot blonde from CAS with money/family aspiration depending on my mood at the time
In last few games, Alexander has ended up fighting Dirk for Lilith and winning coz hes got money in Liliths eyes, though last time I had him cheat on her in college and marry the new girl. Although once I made Mort's new wife move in with a little boy and Alex fell for him when they were teens.
Cassandra I am awful to because she has such ugly babies in my experience, she has married Don before, but usually has one baby catches him in the act and runs off to Darren who happily lets her in. However there have been times that she has been fed up with Mort's new missus that she dumps Don and goes for Darren.
ALthough this game they are not together and Darren is now an elder alone.
Dirk Dreamer I like him so he gets a nice ride usually take to college and make him excel, I let him marry whoever he really likes best male or female (3lightning and they are sold!!) and they have a nice house and kids. This time hes got a lovely girl despite her obsession with exercise.
Don Lothario is cool, he usually becomes a Knowledge sim and an Adventurer so his house looks like he could be Indiana Jones, (can't wait for the new EP so he can really go on adventures) normally he marries some townie or a CAS, although, he wooed the wife of that big family in Seasons and had some pretty kids with her. But this time hes married to Dina who is a family sim now.
Nina Caliente has been ignored or played to death, depending on whether I am bored with her or not, shes been scraping a living selling furniture to pay bills, and been living the life of luxury as Mrs Goth. This time I've made her a Pleasure sim and shes going to go on holiday and come back with a surprise to look after.
The Brokes are a favourite of mine, and usually I get Brandi remarried to a suitable townie and having more kids (she has had girls on the homelot before), Dustin and Beau get their names changed to Zack and Frankie, Dustin has married Angela Pleasant if I plan on him becoming a regular guy, if I make him rich, he snubs her and gets a huge house.
However this time I've not let her remarry and is working hard, shes saved enough by now to move to a nicer home so I'm proud of her.
My relationship with the Pleasants is weird, I don't like Mary Sue or Angela and adore Lilith and Daniel (even though I disagree with his morals) I've kicked Daniel out before and moved the Oldies in, Mary Sue has a makeover and bags a much younger college man who when she died ended up with Angela.
This time I aged Lilith down to child, had Daniel kick Mary Sue out and she moved in with the Oldies Angela ran away and went to live with her, and Daniel married Kaylynn and had a baby...
However whats interesting is that he has dreams of Mary Sue, and constant wants to ring her, talk to her, play with her etc!
SO thats what happens to my characters!