A peek into my messed-up Pleasantview
For context: This is a combo Pleasantview-Strangetown that I started with all the ancestors. The elder and adult playables were created in CAS with correct genetics and started out as toddlers, children, or teens (with the exception of Cassandra, who was born in game). As a result, things have not gone according to canon. This hood was not hard to make, just time-consuming, and required some downloads plus at least one mod (I used the Sim Blender).
Goth: As head of the oldest and richest family in Pleasantview, Gunther Goth served as mayor until his death. His son Mortimer was all set to marry Bella Bachelor, as planned by both families, when Olive Muenda strolled into their wedding party and kissed up Mortmer's arm. This caused Mortimer to immediately break up with Bella and marry Olive in his place. They have started the very successful Goth Laboratories together, but Olive is secretly considering moving back to Strangetown.
Bachelor: After getting dumped by Mortimer, Bella immediately had a rebound fling with Nicolo Lothario in the photobooth, and Cassandra was the result. She didn't continue that relationship but did make sure that Cassandra knew both her father and her half-brother, Don. Bella dated a lot of men while pursuing her artistic ambitions, but she fell for sophisticated, older Xanthos Salamis from Strangetown, and they married and had a son.
Landgraab: Malcolm came to Pleasantview with two goals--start a successful business and find a wife--and he has achieved both. He is CEO of his company and is grooming his heir, Malcolm II, to take over when he is of age. Malcolm's wife Glabe is sister to Glarn Curious and an avid socialite. Malcolm does find time in his busy schedule for the occasional affair. He is currently also in love with Nina Caliente.
Pleasant: Daniel's first love was Michael Bachelor (who still hasn't gotten over him but has since moved to Strangetown), but his ambition was to start Pleasantview's first professional soccer team. He thought Mary-Sue Oldie would be a great partner for him in that endeavor. Mary-Sue, for her part, wants to be mayor and also thought the marriage would help her achieve her career goals. It is a marriage based on convenience more than love, although they do respect each other. They have just had twins: much-adored Angelo and much-neglected Lilith. Daniel's sister Jennifer had to move in after her recent break-up.
Burb: John and Jennifer had been together since they were teens; in college she accidentally got pregnant. She went back to Pleasantview to wait for John, and they planned to get married. Everything was perfect until John slept with some dormie at Don's graduation party and ruined it all. Jennifer left him to raise their son Kevin on his own.
Oldie: Mary-Sue is adopted, but she is the biological daughter of Herb from a fling he had on a business trip. Coral should have known better then, but eventually she found out about Herb's cheating ways and kicked him to the curb. She has found a much better partner in Gabe, and despite their advanced ages, they wanted a child, so they adopted Amy.
Dreamer: Darren is a very talented artist who thinks he can make it to visionary status. He started dating Darleen Matlapin as teens, and they got engaged in college. But he became obsessed with this dormie, Sarah (the same one John ruined his life for). He couldn't keep away, and Darleen found out while she was pregnant. She left Darren with their son Dirk and moved back in with her family, heartbroken.
Broke-Lothario-Caliente: Skip and Nina dated as teens, but in college, she and Don quickly got together. She got pregnant about halfway through and had to drop out. Skip didn't go to college, so Nina and Skip decided to share a place. When Don graduated, he moved in with them, and they became a throuple--although Skip and Don seem the most in love. Nina is still very hung up on Daniel Pleasant and has taken a few other lovers as well. Don and Skip also do most of the childcare. And where's Brandi? She is still single and roommates with Ajay Loner and Erin Beaker, living in a "singles" household. She and Skip never had any chemistry whatsoever.
Caliente-Curious: Another long-time couple, Dina and Lazlo got married right after college, moved to Strangetown, and had their son, Elvis. They have a chill, semi-open relationship--Lazlo has been kinda seeing Brandi Newbie, and Dina has gotten very close to her next-door neighbor, Michael Bachelor. They are very happy together, though, and are considering moving to Pleasantview for Dina's journalism career.