Here are a few that I could remember right away.

Legate Rowan Varrus, Thane of Hjaalmarch used to visit the Jarls’ court pretty regularly when she was home. She didn’t think much of Jarl Elisif the Emptyheaded, so she wanted to exert as much influence on her as possible. Unfortunately this occurred in the vanilla game so it was very, very boring.
Before his marriage to sweet Sylgja, Big D used to drink the Bannered Mare dry and then break into Ysolda’s house to see if he could get lucky. This happened every play session while he lived in Whiterun. During long play sessions he would resort to drinking the Drunken Huntsman dry on the second night, since we hadn’t saved and reset Hulda’s inventory.
Back in the early days when the game was still getting patched Jensa used to put on her Amulet of Mara for Erik the Slayer every time we got an update. She was hoping that someday he would be fixed and finally return her interest. Eventually she hooked up with Stenvar and quit pining after Erik. Mostly.
Jensa’s statue of Dibella has never sat upright. It’s tossed behind the bed at Hjerim next to a pile of leather strips and a basket full of lavender, Dwarven oil, and troll fat. I suspect that Jensa’s status as champion of Sanguine has something to do with the statue’s disapproval.