''Heartache 101: ~Sour Into Sweet~'' is a [[FreewareGames freeware]] customizable DatingSim created by flowerthief, previously known for ''Idolcraft''.

One day at school, [[OrdinaryHighSchoolStudent Nameless Protagonist]] (well, his default name is Kazuhiko) agreed to a bet proposed by his childhood friend Miki, following a conversation regarding their respective skill (or lack thereof) at finding someone to date. Under the conditions of the bet, the two of them would be given 101 days to find and hold onto a significant other. If either of them were to succeed at these criteria while the other failed, they would be considered the victor.

Working toward the goal in order to prove himself to his friend, the protagonist meets many girls.
* Miki Nakajima, The Protagonist's tomboyish [[ChildhoodFriends childhoood friend]]
* Keika Ikeda, Miki's [[RichInDollarsPoorInSense rich and eccentric]] friend
* Tsubasa Onishi, a girl who [[AmateurSleuth solves already-closed detective cases]] given to her by her father to keep her mind sharp
* Shihoko Kaneshiro, the SchoolIdol and star of the tennis team
* Riho Kaneshiro, Shihoko's [[AlwaysSecondBest overshadowed younger sister]]
* Akari Sato, a shy acquaintance of Keika's who suffers from neurotic disorders
* Hinami Hiraoka, Akari's [[GenkiGirl overly energetic]] friend who frequently misses school to travel overseas with her family
* Chiemi Akizawa, the [[GuideDangIt hard to find]] SecretCharacter
* [[GameMod and many, many more possibilities, since it's entirely possible to code your own custom characters into the game.]]

The game can be acquired for free at [[http://rpgmaker.net/games/3229/ RPGMaker.net]]
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!!This work provides examples of:
* AbsurdlyHighLevelCap: Stats go up to 100. While raising these stats to max value will continue to increase the affection bonus from talking to girls, it is still possible to max out affection levels within the time limit without doing so. The other uses of the stats are storyline attribute checks (which never require values higher than 50 in the core game) and giving advice to girls (which will have a 100% success rate somewhere between 50 and 60).
* AccidentalPervert:
** Protagonist is subject to this often. Ranging from accidentally catching a glimpse of Tsubasa's panties when she falls over to falling and landing on top of Miki if an early Athletics check is failed. Riho witnessed the latter, and presumes he intended to land on Miki.
** Riho herself becomes one later, when she accidentally grabs Protagonist's crotch area trying to catch a pen rolling off the table.
* AlwaysSecondBest: While she never displays anything other than love for her sister, Riho feels that Shihoko is better than her at everything.
* AmateurSleuth: Tsubasa, who works out the solutions to already-solved cases given to her by her father as a form of training.
* TheBet: One of these kicks off the plot. The protagonist and Miki each bet that the other can't get a significant other within 101 days.
* BigBrotherInstinct: Hinami's brothers are very protective of their little sister, as the protagonist will discover the hard way if he attempts to court Hinami.
* BoyfriendBluff: Early on, Miki claims to have a boyfriend. This turns out to be a serious exaggeration.
* BreakingTheFourthWall:
** The Chocolate Lady, who's apparently somewhat aware of how unrealistically small the in-game world is, and expresses her displeasure of the random generator that forces her to walk around town and share her [[InfiniteSupplies always sufficient supply]] of chocolates with strangers every day.
** The random encounter with the drug dealer has him and the protagonist talking about the stats, with the former claiming his stats are on the 4 digits and the protagonist claiming they only reach 100
* BrilliantButLazy: Tsubasa at studying. Although she is capable of scoring high grades, she often skips school to do detective work.
* BrownNote: Requiem of Surrogation.
* BrokenAesop: It's entirely possible to call out Shihoko for flirting with all the boys after she's agreed to become exclusive with you... while dating up to six other girls, including Shihoko's little sister, at the same time.
* TheCasanova: Shihoko is a gender flipped version. Surprisingly, nobody seems to take much issue despite her not being a guy, outside of the time she was told to choose between two people and told them both individually that she chose them because she wasn't used to them not being okay with it.
* {{Catchphrase}}: "Hold your horses!" for Hanami.
* ChildhoodFriendRomance: Protagonist and Miki
* ClingyJealousGirl: Riho will become this if both her and her sister Shihoko fall in love with Protagonist. It reaches a boiling point when, after Shihoko acts affectionate and clingy towards Protagonist right in front of her, Riho throws the lunch she made for her in her face and runs off. [[spoiler: And then later on after that, Shihoko tries to take Protagonist into the locker room to make out. Riho reacts by dragging Protagonist outside of the school, pinning him to floor, and slightly undressing in front of him, threatening to tell her sister about this event if he goes into the locker room with her.]]
* CompetitionFreak: Miki always wants to compete with Protagonist over trivial matters.
* CovertPervert: [[ShrinkingViolet Akari]] gets more and more funny ideas the more she likes the protagonist. Goes way over the top after she falls in love with him:
-->'''Akari''':[[spoiler:I got another pillow.]]\\
'''Protagonist''':[[spoiler:You what?]]\\
'''Akari''':[[spoiler:Another pillow. There's room.]]\\
'''Protagonist''':[[spoiler:Another pillow?]]\\
'''Akari''':[[spoiler:Yes.]]\\
'''the protagonist''':[[spoiler:For what?]]
-->'''Akari''':[[spoiler:For...you know....]]
-->'''Protagonist''':[[spoiler:I don't know.]]
-->'''Akari''':[[spoiler:When you sleep over.]]
-->...
-->'''Protagonist''':[[spoiler:Wait, "there is room", you said?]]
-->'''Akari''':[[spoiler:Yes.]]
-->'''Protagonist''':[[spoiler:So...there is room for the other pillow?]]
-->'''Akari''':[[spoiler:Yes.]]
-->'''Protagonist''':[[spoiler:So then both pillows are being used at the same time.]]
-->'''Akari''':[[spoiler:Yes.]]
-->'''Protagonist''':[[spoiler:In the same place.]]
-->'''Akari''':[[spoiler:Yes.]]
-->'''Protagonist''':[[spoiler:In your bed.]]
-->'''Akari''':[[spoiler:Yes.]]
* DerailingLoveInterests: Somehow they have to make it moral for the protagonist to take Keika from her boyfriend. Specifically, [[spoiler:her boyfriend Shoichi turns out to be a gambling addict who spends Keika's money on pachinko machines, and he no longer loves Keika, resulting in the two of them breaking up. The protagonist can then date Keika guilt-free.]]
* DrugsAreBad: There's a drug dealer who will offer to give you a special pill that boosts all of your stats considerably. The downside? The withdrawal is absolutely ''painful'' -- a few days later, your stats start randomly ''dropping'', sometimes to the point where you're actually worse off than you were before taking the pill.
* DevotedToYou: Chiemi to the protagonist.
* EasyLevelTrick: There are ''lots'' of bonus items and features scattered throughout the game that give Protagonist an extra edge in boosting his stats or his chances with dates. Probably the most famous of these are the chocolates, which are handed out by the ridiculously meta Chocolate Lady.
* EveryManHasHisPrice: Keika tries to bribe other students in the class to get them to date Miki. [[spoiler:It doesn't work, and the protagonist calls her out on it]].
* EyesAlwaysShut: Keika's default expression has her eyes closed, though she does open them up in some of her other portraits.
* FirstGirlWins: Can be both true and averted depending on your choices.
* FreudianExcuse: Riho starts off on the worst terms with the Protagonist, but as time goes on, it's rather obvious that she has an inferiority complex over her SchoolIdol sister, Shihoko, which has led to her becoming an utter {{Workaholic}} to make a name for herself. All this does is stress her out even more and leave her a rather cranky mess when the Protagonist first meets her.
* GameMod: One of the features of the game is that it is relatively easy for people to create images, profiles, music, and stories for their own characters and add them to the cast.
* GameplayAndStorySegregation: Miki is supposedly the childhood friend of the protagonist, but they begin the game on "Neutral" terms. Either the game felt the need to make it a tad more difficult to romance her, or [[WeUsedToBeFriends the vitriol between them has created a genuine divide.]]
* TheGloriousWarOfSisterlyRivalry: Shihoko and Riho are almost a textbook example.
* GenkiGirl: Hinami is full of energy. Miki and Shihoko can be rather energetic at times, as well.
* GoGetterGirl: Riho.
* HeterosexualLifePartners:
** The Protagonist and Takuya evidently have this dynamic, being the guy that interacts with you the most throughout the game. He also appears as a rare space on the board where he'll invite the Protagonist to hang-out after school. These hang-outs offer sizable stat boosts.
** For the girls, Miki and Keika also have this going on.
* HeWhoMustNotBeSeen: Literally every male character in the game. Only the girls have character portraits, though Takuya has a sprite on the progress board.
* [[HoistByHisOwnPetard Hoist By Her Own Petard]]: If you choose Akari's route, Keika only set her up with the protagonist because Keika thought Akari would be so unsociable that the protagonist would lose his bet with Miki over who can get a significant other first. If the protagonist does manage to win Akari's heart, then Keika actually causes the protagonist to ''win'' his bet with Miki instead.
* ImprobablyFemaleCast: Sure, it's supposed to be a dating game, but out of the male characters shown (Takuya, Masashi, Yoshinori, Hiro, Shoichi, Freddy and Sammy, and a few others), most of them only appear in one or two scenes. The closest one to even becoming a RecurringExtra is Takuya, and he fades out of prominence extremely quickly.
* InJoke: The dev team has made a habit of referring to the Content Creation guidelines as an [[TheMaker object of worship]], cracking subtle (or [[ThatsWhatSheSaid not]] [[DoubleEntendre at all]] [[HehHehYouSaidX subtle]]) dirty jokes [[ComicallyMissingThePoint out of context]], as well as blatant references to the ''VideoGame/MightAndMagic'' series and various bits of [[{{Otaku}} Japanese pop culture]] [[GeniusBonus nobody but them ever understands]] at every opporturnity, both in the game and especially on the forums.
* JerkWithAHeartOfGold: Riho starts off not a fan of the Protagonist, but can warm up to him as time passes. It's rather obvious that her usual unfriendly demeanor comes from a combination of both being stressed out from constantly overworking herself, and feeling like she's trapped in her older sister's shadow. She's much friendlier in a casual setting.
* JokeItem: The top. Purchasable from the convenience store for only 200 yen, this item can ''only'' be given to Tsubasa or Hinami (technically, it can be given to anybody, but everybody else considers it to be a bad gift, and thus there is no benefit to doing so)
* LoveTriangle: Downplayed, but if Hinami and Akari both have high affection for the protagonist, there are some events where they both want the protagonist's attention, though it's downplayed as they're very nice to each other about it.
* LovingAShadow: Chiemi.
* MarshmallowHell: [[spoiler:Keika accidentally subjects the protagonist to this when he's teaching her to swim, pushing him under the water when she thinks her boyfriend is around.]]
* MaybeMagicMaybeMundane: It's never made clear whether [[spoiler: the ghost of the dead composer]] that appears to Akari each night is real or simply a hallucination.
* MediumAwareness: The Chocolate Lady knows that she's an NPC in a DatingSim, and thus gives hilariously fourth-wall-breaking advice and commentary which leaves poor, GenreBlind maincharacter confused.
* NiceJobFixingItVillain: The protagonist needs a girlfriend to win his bet against Miki. Keika (Miki's friend) agrees to arrange a meeting between him and Akari to help him out [[note]]Keika had already helped Miki out by bribing boys into asking her on a date, and thus her rationale for helping the protagonist was that it would restore her status as a neutral party[[/note]]. Her intent was that Akari would prove to be so [[ShrinkingViolet antisocial and unapproachable]] that any time the protagonist spent with her may as well have been wasted... up until the protagonist ''actually'' manages to get close to Akari.
* NotWhatItLooksLike: While racing against Miki, the protagonist trips and falls, landing on top of her. Miki's classmate, Riho, was watching at the time and concludes that the protagonist meant to end up on top of Miki.
* ObliviousToLove: the protagonist to Miki's.
* OrdinaryHighSchoolStudent: the protagonist
* ProneToTears: Chiemi can easily burst into tears whenever she's overwhelmed or her feelings are hurt.
* ReturningToTheScene: [[spoiler:In Tsubasa's second Mystery, the perpetrator knocked out the owner of a jewelry store, stole only his ATM card, withdrew all money from his account, and then returned the scene to plant the card back on the victim. This prevented the nature of the crime from being discovered until the victim was released from the hospital.]]
* RichInDollarsPoorInSense: Keika comes from a wealthy family. She also has a personality occasionally bordering on CloudCuckooLander.
* SchoolIdol: Shihoko is the most popular girl at school and is idolized by both genders.
* SecretAdmirer: If you visit certain locations on certain days, people will come up to the protagonist and hand the protagonist notes from a secret admirer, thanking the protagonist for events the protagonist cannot recall. [[spoiler:The notes later turn out to be from Chiemi.]]
* SheIsNotMyGirlfriend: the protagonist and Miki
* ShoutOut: [[VisualNovel/{{Ever 17}} Of course I knows the hacker.]]
* ShrinkingViolet: Akari.
* SiblingTriangle: Can happen with Riho and Shihoko.
* StalkerWithACrush: Chiemi.
* StrongFamilyResemblance: The only major differences between Shihoko and Riho's designs are that they have different haircuts, and Shihoko's bust is larger. They even have the exact same "Lovesick" expression. It's a wonder the Protagonist didn't realize they were sisters sooner.
* TheSpock: Tsubasa is the embodied logic.
* TeacherStudentRomance:
** Shihoko. [[spoiler:[[SubvertedTrope Subverted]]. While it first appears to be this, Shihoko is actually looking for ways to deflect her trainer's advances without getting on his bad side]].
** Takuya mentions at one point that he seriously fell in love with a teacher from Australia, but this isn't really expanded upon.
* ThereAreNoTherapists: Played with. Akari is being treated by the school counselor, but it soon becomes clear that he's out of his depth since he's an ''academic'' counselor, not a ''psychological'' one. She's also receiving treatment from the local hospital. [[spoiler:She refuses to take the medication because it doesn't help one bit, and soon she stops visiting altogether]].
* ThoseTwoGuys: Yoshinori and Hiro, two guys in the Protagonist's class who he tends to overhear talking to each other. They'll occasionally appear after school to ask for a favor from you. [[{{Jerkass}} Neither of them are very pleasant people]].
* {{Tsundere}}: Miki and Riho both, though Riho is a surprisingly traditional example of this trope. After initially hating the Protagonist, she can grow to befriend or even fall in love with him.
* UnexpectedGameplayChange: Most of the game is a VisualNovel[=/=]DatingSim. The school day itself is a kind of BoardGame-like challenge, with dice-rolling and items that move you a certain number of squares. The Protagonist's part-time job as a janitor requires the player to beat a level of either VideoGame/PacMan [[note]][[NintendoHard without power pellets]][[/note]] or a StealthBasedMission.
* UnprovokedPervertPayback: Riho, propagating that the protagonist is a creep.
* VitriolicBestBuds: Protagonist and Miki.
* WorldOfJerkass: Most of the boys are perverts or all-around jerks, many of the girls are cold to you when you first meet them, some of them actively attempt to sabotage your chances of winning the contest, and the Protagonist himself is far from a saint regardless of player input. Shihoko and Hinami are about the only truly good figures you encounter throughout the entire game.
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