The game is a micro-managing dating sim. This means that in order to "win" each route, you must dedicate your incoming in-game days to stat building and setting up dates with each boys and triggering certain events.

Every in-game Sunday, you must schedule your upcoming week, Monday - Sunday. If you obtain any of the boys' contact, then you can ask them out on a date or call them to talk. In the menu of their contact, it also displays a heart that serves as a color coded indicator of their affection towards you.

At the beginning of each month, starting from November and ending in June, the general total of your stats (from studying elements) is added and tested against a sort of benchmark. If you fail this benchmark three times, you are expelled from the school.

The outcome of each route depends on your ability to make correct decisions in important story choices, raising their element's stat, and raising their affection.

Your schedule menu several components. There are the hearts next to each box that corresponds to one of the upcoming weekdays, there are the two bookmarks that shuffle upon being clicked, and then there are the activities which you can choose from.

First Bookmark
The first bookmark contains various studying activities your character can choose. Each one will add fatigue and a particular elemental stat to Leia

The first one is wind, the second is fire, third is light, fourth is water. The last three is, in order, elective study, sleep, and free time.

- wind/fire/water/light -
+10 Respective Element, +5 fatigue

- elective study -
random + 3 to 5 points in all of the elements, +7 fatigue.

- sleep -
- 40 fatigue

- free time -
you can visit anywhere on or off campus, buy items or get contacts on this day. if you visit a place that's neither a talking place with a boy or a merchant area, one of your elemental stats will decrease or increase from around 2 to 8 points, and/or your fatigue goes down by 8 points. You can visit any two places, but you cannot visit the same place twice in the same day.
When your overall fatigue hits around 55-60, the amount you learn of an element lessens in the coming days. When your fatigue hits 100, Leia will spend that day sleeping instead of whatever activity you plan.

If you plan a date, you must put a free-time tile down on that date to meet up for it, otherwise Leia will forget. You can visit a place before the date, but you cannot go on a date and then visit another place after it in the same day.

Second Bookmark
The second bookmark is your work bookmark. When you choose any of these tiles, Leia will go to work at that place. There is also a free time tile in this bookmark, which functions the same as the one in the first bookmark. In order from top to bottom, when you unlock all of them, the tiles are: Library, Amusement Park, Church, Magic Shop, Cafe, Item Shop, Free Time

Maid/Waitress [At the Cafe]
+10 Fatigue, +/-10 Gold, +5 or +10 Crystals
[Unlock] Visit the cafe once. You can also purchase items from the store after this.

Merchant [At the Store]
+10 Fatigue, +/-10 Gold, +5 or +10 Crystals
[Unlock] Visit item store once. After this, you can also purchase from the store
when you visit in your free time. Note: The items in the store are random.

Church
+10 Fatigue, +5 Light Element, +10 Gold
[Unlock] Visit the Church once without any of the boys being there

Amusement Park
+10 Fatigue, +5 Fire, +10 Gold
[Unlock] Visit the amusement park twice without any of the boys being there.

Library
+10 Fatigue, +5 Wind, +10 Gold
[Unlock] Visit the library once without any of the boys being there.

Magic Shop
+10 Fatigue, +5 Water, +10 Gold
[Unlock] Visit the Magic Shop Twice. You also unlock usage of the shop afterwards.

Heart Encounters
The hearts with boys' faces in them serve two purposes.

One, to tell you that you can get that boy's contact if you scheduled a free time tile during that day and you happen to see him,

Two, to tell you that an event related to that boy's Affection and Stat level can be triggered on that day. This event is independent to whatever you have going on that day, so you can be sleeping or dating that day, but so long as your affection and element stat is high enough, you will encounter that boy in an event.

Calling boys, Giving Gifts
You can only call boys if you obtain their contact. In order for you to get any of their contacts, you must talk to them in a scheduled free time period where their heart shows up.

However, even if their heart is next to that day, and you scheduled free time during that day, it's not guaranteed that they will show up in any of the areas.

You can more or less get all of them though on the first week by saving everytime it pulls up the free time menu for these days and reloading until the necessary boy shows up.

When you contact the boy, you have the option of talking to them or asking them out on a date.

In your contact menu, it will tell you your Affection Level with that boy via color codes.

In order of progression, the colors go from

Blue > Green > Gold > Pink > Red

red being the maximum point of affection. Affection is raised or dropped by certain choices in the story and going on dates/giving gifts.

Talking to them is useful only for finding out what their Favorite Items are. It doesn't increase anything else, and if it does, it's not by a significant amount. After finding out their favorite item in game, the item image will show up next to their affection level heart.

Dating them pulls up a calendar and places to go out on dates. From what I understand, whether or not they reject the date is random, and has very little to do with how much they already like you or respect you. So you can ask them out by the second week. In order to go on the date, you must figure out what day it is in your schedule and put a free time tile down. Then you meet them at that particular area.

When you go on dates, you have the option of giving them gifts. They only want gifts they like, don't buy them anything unless you know what they want. There is a cheaper version of what they like, and an expensive version. The expensive version will raise their affection faster. This is the only time you can give gifts.

General tip is that if you don't have a gift for the boy, don't go out with them, because it's not worth the loss date, and there is very little to gain from going out with them besides raising affection stats.

They are also not picky as to where to go from what I've seen. If he keeps rejecting you on a date then it's probably bad luck. The only time a guy persistently stopped dating Leia was when I forgot to go out with him as planned three times in a row.

Tests
You get a testscore at the beginning of every month starting in November and ending in June. The aggregated score is more or less based off of the total of your two highest Element Stats. The tests are a good way of making sure you have enough of the stats you need for each boy, and generally you should only invest in one element for the boy you are pursuing. If you fail the tests three times, you are expelled from the school.

November Test
Pass Mark: 142
December Test
Pass Mark: 280
January Test
Pass Mark: 423
Feb Test
Pass Mark: 565
March
Pass Mark: 694
April
Pass Mark: 837
May
Pass Mark: 975
June
Pass Mark: 1117

Winning Strategy: Senpai will only notice you if you're his element and if you date him and give him gifts until he's red in the heart.

Generally, I get the boy that I want's contact by the first week, which should be feasible since the three main boys all have encounters on the first week, as well as unlocking the job with the element that corresponds to that boy and the Item Shop. If I have time, I also buy as much of their desired items as I need during that week.

After that, my general schedule revolves around my dating them. Ask them out until they accept on the first day of that week, spend the next 5 days studying their element, and then sleep. I start off giving them the more expensive gifts until I run out, and I stop dating them and focus only on studying and sleeping when their heart turns red. So a typical schedule would be:

Free Time
Study
Study
Study
Study
Study
Sleep

Save before you plan a date, so you can reload and try again if they reject you. With the money the game starts you off with, you should have enough to max out their affection without having to take up a job.

Once you max affection with your guy, then you can replace your free time with more study time !!!! After the June test, you can also just spend your time sleeping or completely exhausting yourself without consequence. You generally max out their affection by around mid-November or early December if you start after the first week of scheduling if you follow my advice.

I advise getting their affection maxed out as fast as possible though, as I'm not sure if there's any deadline to obtaining their route. Probably though, I think their events are all on a scheduled trigger.
---------------
Other:

You honestly only need to raise stats that correspond to the boy you're pursuing. Regardless, you're going to have to play the game over from the nearly the beginning because while the plot more or less stays the same (from what I've seen between Leo and Locke), the event triggers differ per boy.

Most choices don't really effect his interest of you negatively, from what I notice. There are a few instances where your boy will just stop dating you though if you choose wrong, but they're more towards the second half of each route. But the general guideline for picking choices is that, you just sort of generally be adorable and honest and pick adorably honest shoujo options. If it asks you if you want to go after him, you gotta go after him. Channel your inner shoujo girl, exercise that shoujo energy. If enough people are struggling though I'll make a guide of choices.

Also, getting crystals is useless so far, you use them for cafe items and to buy dresses, which don't really exhibit much of an effect on gameplay. It's also expensive, and time consuming, because there's a chance you'll lose gold trying to farm crystals, your fatigue goes up twice as high as it does on study days, and you don't learn elements at those jobs, forcing you to time manage better.

Having a job in general is useless because the game sets you up with enough money to max out their affection.

Also, once you get to red, you don't have to date the guy you're pursuing anymore, he won't unlove you once you stop planning dates with him. I'm pretty sure you can date other guys without conflict if you really want to.

Locke:
The Student Body President. Or something. I dunno, he acts important, I assume he is. He's the icy popular one. He plays piano and is a vampire. He's the brown haired one with blue eyes.

-screams- probably the hardest boy to deal with between the three main boys. There are a lot of events where you can just...accidentally not end up with him, and his sad ending has the most obscure condition of this game. Thiis game is still pretty easy in terms of getting cgs/events in comparison to a lot of other ~wild encounter~ type otomes, but not having a guide doesn't really help. ;;

Element: Wind
Gifts: Ancient Book [Good gift], Classical Music Collection [Better gift]

//Mild Spoilers//

Generally you should pass all the monthly tests with your wind stat alone to make sure you hit all his encounters.

Affection level refers to the colored heart in each boy's contact.

Happy End:
- Max out affection level
- Either avoid or resolve his fiancee conflict on May 18th with: Which school is Ann in? > Write her a letter > Tell her you're a friend of Locke's.
- During the fight at the end, use the ring later, rather than immediately.

Good End:
- Don't max Locke's affection, have it at pink.
or
- At the fight during the end, use the ring immediately, rather than later.

Sad End:
- Max out affection level
- Resolve fiancee conflict starting May 18th: Ask what college she goes to > write letter > tell her she is lucky to have Locke. After this, she should send you a very brief letter, and Locke becomes adamant about marrying her.

Dialogue Options:
On March 12th, he'll tell you about his sister. If you pick the first option, which questions his father's actions, then regardless of what you pick after, he effectively ends your relationship.

If you accept his invitation to a gravesite, then you have a chance of dropping his heart to yellow in the next confrontation. If you pretend to clean the tombstone, rather than dry it (presumably you are honest about why you are cleaning it in the second option), then he gets mad at you, and drops affection. You can raise his affection after this, however. Reportedly you can't get the Happy/Sad route if this happens.

On May 18th, he'll update you on his fiancee situation. You can either wish her well, or ask what school she's going to.

In late June, a conversation between you and Locke will trigger if you ignore his fiancee conflict by not writing to her (either on May 18th, say you hope Ann can settle down, or later on, opt out of writing to her). In the June event, if you choose > You are confused > You feel you need to care more about one another > You want to know if he has courage to continue, you can continue on his route. If you choose any others, you will break up with him and end up on the Forever Alone route.

CG Gets:
First CG, Aug 5: Accessed in in the prologue.

When you hear music while in the garden, you check it out, and Locke should be in the piano room, doing his thing.

Second CG: Develop Wind Stat and/or raise affection levels with Locke.

Generally, he should have a preference for you over the other boys by the time of the School Dance (Somewhere either in November or October). He'll ask you to dance, and you must accept.

Third CG, December 25:

Develop Wind Stat and raise affection levels with Locke. By this point my affection with him is usually maxed out.

He'll ask you about the vampire you saw a little before this encounter. Have Leia disregard it (Second option), and he'll ask you if you want to go out with him for Christmas. Accept, and you should get your third CG.

Fourth CG, Feb 14: Triggered regardless of whether or not you've been pursuing him.

Fifth CG, Meteor shower:

You must be on Happy End conditions to encounter this. If you write to his fiancee telling her you are Locke's friend, events will unfold and he will invite you to a Meteor Shower on May 26. If you accept, you must pick the second option, rather than the "You're brave and responsible" one to get the CG.

Sixth CG: Good/Normal end CG with Locke.
Seventh CG: Happy end CG.

Leo is the teacher as well as the school doctor. He's too old for you, but he's pretty open about his bias towards you. He's a kind sort of flirtatious. He's got long pink hair and a monocle.

Element: Light
Gifts: Cottage Rose Specimen [Good Gift], Silver Cross [Better Gift]

Generally raise your light stat in accordance to the necessary test marks needed to pass each month.

Happy End: Raise your affection level with Leo to max.
Sad End: Raise your affection level with Leo to Pink.

You can't break the route once you're in it, but you can completely miss it. On March 3rd, you must go after him [first option] and then deliver the beverage to him the day after, rather than having your friend do it for you. If you don't do these two things, Leo won't love you ;;

Edit: In order to get his good end, you must stay in school. I haven't tested this, but I imagine your safest bet is to continue studying light throughout the semester if you're on his route.

All his CGs are more or less from event encounters that are kind of random? Like they're not significant dates or choices (unless I've just played enough otomes to know what he expects) anything, except for his sad and happy ending cgs.

Also there's an eighth CG of Leo that was just...sort of in my CG set already and I don't really know if I had accidentally triggered something while on another route, but I don't remember it and have no idea what it's from. So if any of you still haven't found the last CG for Leo, I literally have no idea where it comes from.

The unfortunately(or fortunate???) named child of the bunch. We can call him Jesus with a Spanish accent if it makes any of you feel better. I frequently get his heart encounter image mixed up with Locke's, but he's the red haired boy with green eyes. His personality is very, childhood friend, and he's more or less in love with Leia straight off the bat.

He's good with swords, and comes across kind of childish, but he's very protective of Leia.

Element: Fire
Gifts: Kaleidoscope [Good Gift], Hourglass [Better Gift]

Like the others, follow the test progression stats with fire to ensure most, if not all his encounters.

Sad Ending:
- Max Affection/Stat
- At the fight at the end, tell Christ to "Watch out"

Happy Ending:
- Max Affection/Stat
- At the fight at the end, tell Christ to "Catch it!"

Route Breaking Events
From what I understand, you have to have a series of choices pertaining to his subplot, prior to his confessing to you, in order for you to fail in getting his route. It stems from somewhere between Jan 6. to Feb. 28, during the confession CG. I don't believe any other choices would seriously break your route, however.

The choices that should keep you on path should be from Jan 6. till his confession is: Follow him, I have faith in you, I'm not going out, I don't want to lose you, Take care.

After that I'm pretty sure any decision would still keep you on path, even when you misinterpret his letter. u-u;;; he's kind of difficult to not get in that sense.

CG Gets:
First CG, Aug 3: Mandatory Encounter

Second CG, Dec 25: Default encounter if you don't go out with Locke. If you're pursuing him you get some dialogue options pertaining to a carnival though.

Third CG, Feb 28: I don't know if its necessary or not to choose his name in this encounter, but do it anyways because who would this incarnation of you really wish for anyways? If his name doesn't come up, then you've missed his route.

Fourth CG, March 6: Stat/Affection Requirement encounter (my stats in fire cleared test and his affection was maxed)

Fifth CG, April 17: Stat/Affection Requirement encounter

Sixth CG: Sad Ending
Seventh CG: Happy Ending

Unlockable after either playing through the game at least once or achieving any of the boys' routes at least once.

Element: Water
Gifts: Blue Cup, Pocket Watch

Guide courtesy of Sunny , bless their heart omg, for documenting this. orz

For Jesse's route:
Do not romance anyone. You need at least level 3 in Wind, Fire and Light, and have water as your highest stat, at least level 4.

On Dec 24, pick 'Check it out' to get his first CG. If you're on route with any of the other boys, you will still die during this.

Be sure to spare 100 Gold since you'll need to buy something to continue his route. Make sure to visit him at least once a week (you can also get him gifts, the blue cup and the pocket watch).

Happy ending: Finish the game with > 450 Water Magic
Sad ending: Finish the game with < 400 Water Magic

I was able to get all my stats around 300~, where my water stat floated just a little under ~400 either before I met Jesse or just a little over a month after the fact. Since there's four stats, 4x300 = 1200, which is more than enough to pass through the entire game without ever having to study again. So I spent the entire time sleeping u___u;; Until around June. You can then add enough within that month to put you over 450 so that you can get the Happy End if you reload from the start of June with the same stats. The dialogue choices for Happy and Sad stay the same.

Choices: (SPOILER ALERT)
Nothing special > Not exactly > Behaviours > Yes > I'm just coming to bring you something > Nonsense! > Yes, I'll take it (-100 Gold) > I believe that fate can be changed > Yes > OK > Yes (+second CG) > Please take this scarf > No, thanks (+third CG) > I just couldn't help myself > Open it > I was being too obsessed > Check Jessie's drawing book > Jump over the sundries > Kilu won't want to see you like this > ... > Wait here > Write a note > Keep waiting > Don't you want to stay by my side? > Rush up to Jesse and block the sword for him

CGs:
First: Choose to check it out on Dec 24
Second: Choose to follow the silhouette on Feb 20
Third: Choose not to go to Leo on Feb 28
Fourth: Unlocked automatically
Fifth: Sad end
Sixth: Happy end

You get Strength Ebbing Away when he doesn't come for you on the rooftop (I think its just a series of wrong dialogue choices.) You get Come Up A Little Short when you pick the wrong dialogue choice at the end.

Edit: To get Strength Ebbing Away achievement (Jesse doesn't come for you on the rooftop):
Wait here > ( Write a note ) Say it aloud > Keep waiting