This is one of the more dumbass ideas, if you prefer the serious ones please let me know
Warning: Yes yes its mentioned and that but no real description it's just dialogue, but if you've got a creative mind you might start seeing things
Characters Excluded: Cicero, as he is asexual (but not aromantic dw) in my headcannon yada yada I've said this before lol
Also I didnt put who said what so feel free to think whatever

＊*•̩̩͙✩•̩̩͙*˚　　˚*•̩̩͙✩•̩̩͙*˚＊

Ancano
> Wait, did you steal my note book yesterday?? What in Oblivion--

Brynjolf
He didnt say anything in particular, but he did whistle a tune.

Farkas
> Woof

General Tulius
> You know what them damn stormcloak bastards did-
> Honey this isn't the time

Haskill
> WAIT, THE SWEETROLL IS BURNING!
They then proceeded to get dressed real quickly and get the sweetroll out of the oven.

Hermaous Mora
> You know what's better than pussy? A really good book-
> BAE STOP THIS IS NOT VINE

Lucien
> You remind me of my last contract, all the screaming and begging.
> ᴾˡᵉᵃˢᵉ ᵈᵒⁿ'ᵗ ᵏⁱˡˡ ᵐᵉ

Sanguine
> Oh also, I hope you know that guy over there has been watching us-
> Yo what the fxck

Sheogorath
He moved his staff by accident and gravity shifted, jolting both of you (and everyone else outside) upside down on the ceiling in a flash...
> WHAT

Teldryn Sero
> I never got payed for this. Next inn we stop by you're paying.
> :/

Ulfric Stormcloak
> By Talos, those imperials are going to attack Falkreath next, arent they?
> Uh- What?

Vilkas
> I cheated...
> W- What?
> Farkas caught this vale deer the other day... And I took its hide for that competition...
> Oh by the gods never scare me like that again