I think the heart of the dead companions are enough of a romance to keep me happy.
My real life wife spends the day at home while I'm out working, which is not that far from what I described before.
This mod adds a quest to date and win the affections of your maid Eyja (if you have Rosethorn Hall).
Updates include a curtain system that allows you to open and close curtain in the house, package tweaks, bug fixes and much more. Literally had more fun in Oblivion than probably any game of the past decade (and come to think of it, Oblivion is very nearly *last* decade - ouch).
Kharazim is strong due to his ability to jump to allies, and grant them movement speed while healing them.
I can definitely see this guy making his way into may team compositions for weeks to come.
Honestly though, I don't think anything in the vein of adding a 'true' dating simulation has ever been added to the game, though wth Skyrim having the bones of such it might get more mods like it.
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There are mods that let you woo and "date" characters as the whole focus of the mod.
There are some older "romance" companions where all they do is put strawberries in your pack for you.
I managed to get my mitts on a slightly modded copy of Morrowblivion recently and its awesome, even on the Oblivion engine.