I contemplated doing a walkthrough for awhile and wasn't sure I wanted to, since there is no set order to complete any of the quests. So, I decided what I will put here is one way to play through the game. This way will allow you to get all the medals, including the sneaky way to get both Gerald and Jenny's medal in one game. If you notice any errors or have suggestions, please comment below.
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You start in your home village. When you talk to Lucy you find out she is your childhood sweetheart and she asks you to pick up her dress in Port City. She gives you a RECEIPT for the dress. Exit the village and head East to talk to Gerald by the dock. He wants you to kill 4 bandits to protect the area. When fighting bandits if you are low on HP you can return to Lucy and she'll refill your HP every time.
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When you kill off 4 bandits, talk to Gerald again and he'll give you his BOAT which allows access to the water. Enter the lake and talk to the surfer near the whirlpool. He'll ask you for some seasickness powder made from Tiger Claws. You'll get this later. Sail the boat South past Port City and then West around the bottom of the Island, then North and East until you reach a shipwreck. Search it for a GOLD nugget. Then backtrack up to Port City and talk to the yellow merchant to trade the gold nugget for $25. Now, talk to the red merchant and trade the receipt for the DRESS. Talk to him again and buy the BANANAS. If you talk to him a third time he'll talk of flowers so rare they shouldn't be wasted just on a woman. If you talk to Mwelaki he will ask you to kill his rival, Tabitha, who he claims is a witch. The woman near the hotel is April-May and will ask you for flowers. It is useful to buy a CHICKEN from the hotel as it can be used to heal in battles.
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Exit the town on foot and kill the bandit by the bridge. Cross the bridge and get a GOLD nugget out of the cave. Progress North back to your home village and give Lucy her Dress. She will reward you with her father's SIEVE. Travel back down over the first bridge, then West along the river until you see a sparkle in the water. Use the sieve to collect a GOLD nugget.
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Enter the tribal village directly below and talk to Tabitha. She will give you a "friendship bracelet" which is actually the CURSED PENDANT. You will also buy some generic flowers. Note that you can fill up your HP at any time by drinking water form the village well. This is useful if you want to try and kill the elite bandit nearby. Cross the bridge and throw the bananas at the monkey and proceed South to the second tribal village. When you enter you must pay a $5 fine to the chief for trampling the grass and he will give you some "defective" flowers. In fact they are the "Rare" flowers. Go to the bottom right and search the hut with flowers in front of it to get the KNIFE. You can exit the village and and use the knife to kill the tiger and collect the CLAWS. Return to the first village and try to kill Tabitha with the knife. She will use the cursed pendant to mind-control you, have sex with you, then kill you and suck up your life force in a unique way! This death is OK since you will restart outside the village and lose nothing. NOTE: If you get the knife before talking to Tabitha, she won't give you the pendant, you will kill her, you won't get the sex scene, and you won't get the flowers.
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Now you should return to Port City and cash in your gold nuggets and talk to the red merchant again. He will buy the rare flowers for $15. Talk to April-May and give her the generic flowers and she'll want some chicken. After that she'll tell you to pay $8 to the hotel manager and then when you talk to her again she'll have sex with you. NOTE: April-May will accept either flowers. This just allows you to give her the rare flowers if you didn't get Tabitha's flowers. Buy another chicken and take the boat North to the top of the map. Here is the Castle. You'll need to kill an elite bandit to enter. The best chance is to use 2 Medium attacks, and a weak attack. Then Block and heal yourself. (Note, you only heal if your HP is below 30%, however while blocking you still take 0~2 damage so keep blocking until you are low enough to use the chicken)
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Enter the castle and notice a tree is out of line. This path leads behind the castle where the Chinese Doctor sits. He will give you a BOWL and remove the cursed pendant if you have it. (Now you can kill Tabitha) He will also grind up the claws into the seasickness POWDER. You can enter the castle and talk to Jenny. She will sell you the Mountain Gear for $30 which allows you to cross horizontal mountain ranges. There are 5 of these in the game. (see the previous post for an image of the locations) The first is right outside the castle. Head South across the mountains and talk to the fisherman. He wants special velvet worms which are somewhere near the tribal villages. Next, go North of the castle and cross the mountains to search the cave. You'll find a GOLD nugget.
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Leave the castle area and sail back to the surfer. Give him the powder and he'll teach you how to enter the WHIRLPOOLS. First, sail South and enter the whirlpool near the Ogre. You'll come out near a shipwreck with a GOLD nugget. Return to the surfer whirlpool and enter it. Then go South to the bottom and find another shipwreck with a GOLD nugget. Return to Port City and cash these 3 in. Buy the Lv2 Sword and the Lv2 Armor. Kill a few bandits if you are low on cash. Buy a chicken if you don't have one. Now you can enter the whirlpool near the surfer again and then go North. You'll come to an elite bandit guarding the cave of the old hermit.
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When you enter and talk to the hermit he'll offer you 2 items but you can only take one. The Feather or the Pearls... Here is the sneaky way you can get BOTH -sort of. First take the FEATHER. The pearls will disappear. DO NOT EXIT the cave. Instead go to the far North-East and slide down the tunnel. You arrive in you home village. Walk around in front of Gerald and give him the feather. You will get his sex scene and the Medal. DO NOT EXIT the village. Instead close the game, restart it and choose Continue. It will load from you last save point which is... the entrance to the Old Man's Cave! This time choose the PEARLS. You can cross the mountains and talk to the old man again and he'll confiscate your mountain gear. This used to have a quest but now just causes you to lose the gear. Either way if you return to Jenny and she'll accept the Pearls, have sex with you, and give you the Mountain gear for free.
HOWEVER, for this walkthrough, we won't talk to the old man but instead go back down the tunnel to your home village, exit the village and immediately go North across the mountains, kill the elite bandit and grab the SEASHELL that is sparkling on the beach. Return to Lucy and give her the seashell for her sex scene.
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Now, you can return to Tabitha and kill her, getting the Medal, and then go directly North across the mountains and get the VELVET WORMS from the pool above the waterfall. Get a chicken in Port City if needed and finally, return to Jenny in the castle for her sex scene. Give the worms to the fisherman and he'll catch the MAGIC FISH for you. If you want to, gather 100 coins and buy the Magic Shield from the merchant in the castle. Be sure you have a chicken and over 20HP and sail down to the whirlpool in front of the Ogre. This is a small riddle. You must enter the whirlpool from the North or South, then return from the West. Now to beat the Ogre!
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The main threat from the Ogre is his Power-Attack. It will deal TRIPLE damage (-15HP or more) It is easy to avoid though. Just attack until he lifts the club up above his head. Then Block the next round and he'll miss you. Use you chicken when needed and you should kill him easily.
YOU WIN! You should have gotten all the Medals and found every secret! The next chapter will have even more sex, hand-drawn battle animations, a larger map, more quests, weapons, enemies... better everything basically!