I had this sim who wanted to be a big time famous singer when she grew up...as she rose the first few promotions she met a guy and ended up pregnant...so they decided to get married her parents funded a big wedding party in the back yard but when the big moment came...the groom took off (turns out he was a proprietor at a bar but it played really well as cold feet and a quickly changed mind)
My sim got depressed and quit singing for a long time....the child grew up a bit rough around the edges (it was a great time to try the unstable trait) and left and she decided to try singing again and met a Frenchman at one of her shows...they fell in love and again...she ended up pregnant....this time she dodged marriage, which was easy because her boyfriend lived in France
They kept in contact making visits to France and inviting him over to see his daughter and finally my sim decided she would try marriage again....after all this guy was way different
I was surprised to find after making that decision he had moved to my neighborhood (didn't have to invite foreign visitor anymore just call him) I was even more surprised to find that be had become an elder....who cares my sim said, this is my kid age daughters father and she was an adult anyway
I selected the propose interaction on him in front of a few other sims also and she walked over to him.....of course he (and another random sim in my back yard) in that exact moment died of old age....the reaper came for the person in the back yard first and the entire time they just started at each othed....I couldn't cancel her action or move her at all and she had the saddest look on her face
https://i.imgur.com/DR62hTq.jpg
https://i.imgur.com/xH2vbyB.jpg
Even the French sim didn't move the entire time the reaper did his thing until it was time to jump into the urn
https://i.imgur.com/TJmbZIr.jpg
The wait was very long and it all happened in front of the entire family....my sim quit singing again and went into composing....never really making it far and died pretty young for an elder (I forget how long I just remember her dying young as her while life stood out to me)
It's certainly not as sad as the OP event but it was quite sad to me