Get a friend or two and try to do “difficulty 20” quests. Other than that… I guess you just try wandering around until you can find some enemies you can kill for good xp + silver. For about your level, the white wolves in coldwoods (two or three screens left of the entrance) is where I spent a decent amount of time.
But to answer your question more directly: yes, you do need to go into the same room 15x in a row sometimes. Once you unlock Bleakwoods and are around level 40, you’ll be going in and out of one dungeon for five or six levels at least.