Anacano:

Anacano had gotten word that he had to leave Skyrim and go home for a little while. He was devastated. He couldn't tell you. He didn't want you to be sad. He sat on his bed crying quietly trying not to wake you, but you woke up and saw this and got out of yours and went over to his "Anacano are you okay my love?" You asked him and he shook his head "I have to leave and go home for a little while" he said and you hugged him "How about I go with you" you offered and he smiled and nodded

Brynjolf:

Brynjolf wasn't really one to cry but he did when it came to you. You needed to go on a little mission. It was cross country from Whiterun to Solitude back Whiterun then to Windhelm then back home to Riften. He knew you were coming home soon but he missed you. You got to come home early and you came up behind him and heard him crying "Bryn what's wrong"  you asked. He whipped around and hugged you "You're home lass" he said "Yeah I'm home"

Cicero:

Cicero was upset because he felt he failed the Night Mother (Before you became the listener). You came into his bedroom and saw him crying "Cicero? My jester? What's the matter" You asked and looked at you "Cicero failed Mother" he said "No you didn't. You might not have found the listener but it's okay she or he is still out there." you said. Cicero smiled "Cicero thanks you (Y/n)" he said and hugged you kissing your forehead.

Farkas:

Farkas doesn't cry but he does get pissed. He was punching  dummy with no shirt on making you drool. You could tell he was pissed because he was about to break the dummy. You came to the side of him because you didn't want to get hit. You touched his arm and he looked at you his eyes and they were bloodshot and puffy. You hugged him and he hugged him back and cried into your shoulder "I'm right here Farkas" you said and rubbed his back. 

Ulfric:

Ulfric doesn't let it show. But you do see him come back with a black eye and a bloody lip. You're sure he did worse to someone else.

Vilkas:

Vilkas unlike his brother does cry. You would set him rant and or cry on your shoulder or chest. You  always felt bad for him and when he has a breakdown you are always there no matter what. You even cuddle with him like a child. When he's done he'll ask you for a back rub and you gladly give him his request and falling asleep in each other's arms.