Have you done all this things? You can't go alone to the forest to find Caleb, you need to do the "Looking for Caleb" talk with Bernard at night and win the various fights against the werewolves (if you fail you can retry the following night).
LOCATION | OPTIONS | OPTIONS | REWARD | UNLOCKED AFTER… | STORYLINE | HEART |
BARESHADE | GENERAL STORE – TALK | Ask about the hunt | Ask about his friend; End Shopkeeper’s Sickness storyline | FM23y | BI07 | |
FOREST | GO TO THE COTTAGE | HUNT | Ask about the hunt; Fr: 18:00-24:00 | FM24 | BI08 | |
-x-Sleep in one bed | L40 | FM25 | BI09 | |||
-x--Stay close | First H | FM26 | BIend | |||
BARESHADE | GENERAL STORE – TALK | Talk about the hot spring | First Heart | FM27 | BII01 | |
HOT SPRINGS | Wait for Bernard | Talk about the hot spring- Agree or Tease him a little, Sat/Sun: 18:00-24:00 | FM28 | BII03 | ||
-xx-Sit close to him-Look at him | Second H | FM29 | BIIend | |||
GENERAL STORE – ENTER/LEAVE THE SHOP | BERNARD’S INVITE TO VISIT AFTER WORK | Ask about his well-being after antilycan?; Second H | FM30 | BIII01 | ||
GENERAL STORE – TALK | Plans for the night | Second Heart; 20:00-24:00 | FM31 | BIII02 | ||
Stay for the night | 20:00-24:00; Plans for the night | FM32 | BIII03 | |||
-Stay | Third H | FM33 | BIIIend | |||
GENERAL STORE – TALK | Looking for Caleb-Yes | +3L | Third Heart; 20:00-24:00; Wolf’s bane; Antilycan | FM34 | CI01 |
If something is unclear or my comment doesn't help let me know.