alright so i figured out the unhappy man quest
1: goblin area, the rock gathering stuff top right next to a rock
2: special training area
3: roper forest at the water area
now what i'm stuck at is figuring out where the date for karen is xD
Three dates you need to find for Karen:
1. Guy standing in front of the baths (left of the old guy)
2. Guy by the sign right inside the main entrance to the Underground (immediately after going down the stairs to enter Underground area)
3. Guy in the noble district. I forget which one or where exactly though, I believe he was outside like the other two dates were. Talk to everyone, you should find him rather quickly (this was the last one for me to find and as soon as I unlocked the noble district I found him right away)
You need to Progress Karen's Story three times to see each date. You can talk to all three guys beforehand to arrange the dates though, so find all 3 first then just go through Karen's events repeatedly until done. Then there will be a scene for you to see in the noble district related to Karen's search for a partner.