Your mission is to help her prepare for the final round of Chuunin exam.
Because there is almost no market for true Dating Sim games outside of Japan, it's a frequent misunderstanding among western gamers that "Dating Sim" is the general term for all ren'ai (romantic love) games.
In fact, many romance games are Visual Novels, which is a much different game style.
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Give them the $300 item during the date, and make sure you kiss at the end. Afterwards, just make sure you raise his exp to 4000 and he has full heart counters. (All Naruto-related material in the US is now copyrighted by the series' new owner, Toonami on Cartoon Network.) I was pretty turned off by the bad animation.
After he levels, visit his room and select "other". I was influenced by my g/f and all of the other Sasuke/Sakura fangirls out there.
At day 51 you should see Shika appear in your room. ------------ NOTE: To get the hentai scenes for the 3 main char, make sure that you do the following to get to date level 4 with that char.
to 99 (Naruto-chakra, Lee-strength, Sasuke-intell.) 2. Then go to the new area that opens up and buy their item for 0 (Naruto-Outskirts, Lee-Plains, Sasuke-River) 3. If you do not kiss, you will have to buy another of the 0 item and try the date again.
Cause I offenly get to a quiz that I like, but it is too short, and over quickly. Five boys, since my imagination ran out for description at the end. But I WILL be nice enough in telling you that the quiz includes; Rock Lee, Neji Hyuuga, Naruto Uzumaki, Sasuke Uchiha and Kiba Inuzuka.
I hope you will enjoy this VERY long quiz, which I made so lengthy on purpose.
(See for example, the difference between the series, which is very close to a Visual Novel style of gameplay, and the DOA Xtreme series, which is the closest thing to a true Dating Sim with mass-market appeal in the US.) If the game plays out like a Choose Your Own Adventure, that's a Visual Novel.