Sims 3, and my first family was John and Kaylynn Allen : )
After some bad starts that were about learning the game and trying different jobs, (and making my very first sim lose bladder control at home :/ ) I picked the criminal career at that point to try it.
Made it to the top, and also maxed cooking. I would hack on days off and realized, wow he’s a work-aholic who will die alone, but I felt comfortable enough with the game now, and had achieved the LTW, and actually had decent money, so I dropped hacking every day and tried socializing. The Sim was named John Allen. The game was not on normal aging, definitely very long life span forgot what the settings were then.
So John went ‘wife-hunting’. Kaylynn Langerak was a young adult at that point in the game and was walking by the house so he ran out and met her. So I definitely have some weird nostalgic attachment to that townie, and have ‘re-married’ her a few times in later games. She was artistic, perfectionist, neat, AND evil- a good match. Don’t remember the last trait. But she became a painter and I was amazed at the money that brought in. I had built a house for the first time, and expanded it several times.
They had a son, who grew up moved into ‘The Commorant’ and joined the Culinary career. He married Sandi French, who was a slob, excitable, and wanted to be an astronaut. I thought it would be a good idea to invite the parents and the in-laws over for a party so they could meet and my 2 sims could meet their parents in law. They invited other people as well, from work and so on.
During the party Molly French dies and Grim shows up (first time I had seen him in the game). I wish I had filmed how that all came together. John and Kaylynn, being evil were delighted about the tragedy and were laughing maniacally, Sandi was wailing, River was there as well and she was crying. It was an amazing debacle and a great sim moment.
The second generation lost contact with John and Kaylynn for a good long while after that. One night, my 2nd gen sim was sleeping and gets woken up, and I got something that was almost a cut-scene of John and Kaylyn getting robbed of every single item in their home. I’ve never seen that again since.