Anacano:

You meet when you joined the Mage's College and overheard him whining about something you didn't really care. He noticed you had a s*** load of books and he helped you even though you insisted he didn't.

Brynjolf:

Your sister Vex told him about you and also told him you were gonna come see her and he took and interest. The first thing he noticed about you was your bubbly personality. He half expected someone just like Vex but that wasn't the case. 

Cicero:

Cicero was stuck. On the side of the road. With his Night mother's dead body and a broken wheel. You were walking and you tripped over the wheel and lost the deer you were hunting. He came up to you and asked for help after he helped you off the ground. You did help him and he gave you shiney clinkey coin.

Farkas:

You were in HUGE trouble. Your father Jarl Balgruuf had seen you were out of your room so you ran and hid. Little did you know Farkas was watching you the whole time from where he sat near the Skyforge. He was so close to laughing his a** off and falling.  

Ulfric:

Your Uncle Galmar had told you to stay put. But you didn't you were playing around with magic with the court wizard. Ulfric had come up to see if his enchanted bow was ready. But he was greeted with your lovely smile. He asked to come in and told you who he was and your jaw dropped and you let him in.

Vilkas:

You meet Vilkas at a bookstore. You ran a bookstore and you were trying to put away books but being 5'11 and the 6'4 shelves were just too high and you broke your step stool. Vilkas saw your struggle and helped out. You thanked him and let him have one book for free.