I didn't see this before posting Sibyl, but funnily enough almost all these questions got answered in her introduction but ill elaborate some!
Jennifer and Pim:
Jennifer and Pim got together after Jennifer and Shrimp had an ugly, very one-sided, break up. Shrimp was happy with his new girlfriend, but still extremely hung up on Shrimpina, even getting ahold of Pim and Charlie/The Smiling Friends again to help. Jennifer and Pim started to get to know one another better, but Pim felt incredibly guilty the entire time because his feelings towards Jennifer resurfaced. Jennifer, on the other hand, was very comfortable leaving Shrimp for Pim.
Jennifer did *not* let Shrimp down easy. She was incredibly blunt on why she left him. For a man who was hung up on her, not another woman.
They dated for about a year before Pim eagerly proposed to Jennifer, which again, loving how into her Pim was, she accepted. Pim and her had her storybook wedding, paid for by Pim himself. Afterwards, Jennifer revealed to Pim she wasn't sure about having a family, causing him to pre-maturely crush his dreams of a large family. Pim struggled, more outwardly than he liked to admit. Jennifer caught on, and it caused some issues between the two.
Then Jennifer got pregnant. Unexpectedly.
They started their family after that, stopping after their third child. They had their three kids within about five years of one another, and Pim took care of a lot of the child rearing. But, when it came to everyone picking favorites (for shame, but they did) Jennifer picked their eldest and only son, Guy.
Pim spoiled his children to pieces, struggling to say no to anything. Every tantrum was inadvertently rewarded. (ex: please stop crying, ill buy you that toy instead!)
That's the why to a degree, that among other issues I'll expand upon.
But Pim post divorce wasn't great, at least for the first year. He was a shell of his former self, only his work and best friend, Charlie, were able to keep him afloat. Since his children weren't around, Sunshine and Guy stayed around their mother and aunt- Sibyl stayed away from everyone. When Florence asked to move in with him, he pulled himself out of the gutter and remade himself.
Now one of the top performers at the Smiling Friends once again, him and Charlie support the office with (Pim's) go getting attitude! (totally not breaking down on the inside at alll)