Step Into September - Outline
by @BewareTheWeebs
Season 1 

I - Ana spends her first day at school and has a goal of meeting her soon-to-be lifelong friends so she can begin the "best years of her life" right. In an attempt to impress the first girl she meets, Anna, she tries to hurry up the science experiment they're working on together. By rushing and disturbing the process, Ana accidentally spills the experiment all over Anna, leaving her first bad impression of the day. 

As Ana lays on her bed, she reflects on her day and decides to go ahead with plan B--"Operation: Friendship!"  

She thinks of everyone she met that day and handpicks which options are best and who would blend well with each other 

                                       1. Connects Hugo and Anna's names with an orange string

I.I - Ana tries multiple times to apologize to Anna while inviting her over for tea, and in a fit of frustration, Anna accepts under the condition that Ana stops bothering her. 

      C - Ana bumps into a dazed Christie once again, but this time Christie drops a little doodle of Venus, a girl from the soccer team, surrounded by hearts. Ana returns it to Christie and gets her to accidentally admit she likes Venus while talking about OPF (Operation: Friendship!). To keep Ana's mouth shut about her "terrible secret," Christie swears to help Ana with OPF

      R - While over at Ana's house, Anna hears Ana out and starts to forgive her until she mentions OPF, which raises questions within Anna. Ana's plan is then revealed to Anna, leaving Anna disgusted with Ana, and she scolds her about how weird it is to be treating people like pawns in a game while packing her stuff and shutting the door on her way out. Ana is left feeling dejected and unsure about continuing OPF any further. 

       A - Christie notices that it has been a while since Ana last talked to her about OPF and wonders if that means that Ana has given up on her plans, therefore open to revealing Christie's secret. She frantically searches for Ana, and to her surprise, finds her with a dejected look on her face in an empty classroom after school. Realizing how selfish her motives were about searching for Ana, she sits down with Ana and lets Ana vent about her frustrations, and realizes why OPF means so much to her, and starts to understand her. Trying to make her feel better, Christie tries to have a heart-to-heart with Ana. In the midst of her comforting, Ana's attention shifts focus onto Aaron and Hugo, who can be seen outside the door. Hugo, once again, dropped his books, and Aaron, without a group of friends around him, helps Hugo, and before walking away, gives Hugo some obvious advice about keeping his books off the ground. Ana is immediately inspired to keep pushing OPF forward, much to Christie's delight yet slight dejection that it was Aaron and Hugo's interaction that inspired Ana to keep going and not her talk (though Ana does appreciate Christie's support and it's made them see each other more as friends than co-workers)

R.A - Christie befriends Venus with Ana's help, and Christie helps Ana befriend Aaron. Upon meeting Christie, Aaron develops a romantic interest towards her, enough to comply with Ana's OPF plan as long as Ana does favors for him (e.g doing homework, getting lunches, snacks, etc.). In exchange for these favors, Ana asks Aaron to hang out with Christie and Ana from time to time and to be friendly towards Hugo (her actual goal of the agreement). 

          1. In a last attempt to fix her chances of making Hugo and Aaron full-fledged best friends and integrating both of them into her Christe-and-Ana duo, Christie invites Aaron and Ana invites Hugo to a museum without Hugo or Aaron knowing. As Aaron and Hugo "unexpectedly" see each other at the museum, both Ana and Christie "cancel" their trips with Aaron and Hugo via text, and just as an annoyed Aaron was about to leave, Hugo asks if Aaron would like to explore the museum with them instead. With having nothing to do (except homework but who cares), Aaron decides to stay and visit the museum with Hugo. 

            2. Ana and Christie follow the two carefully behind until near the end of Aaron and Hugo's seemingly dull trip, where a random guy picks a fight with Aaron about "personal space" and just as Aaron was about to throw the first punch, Hugo steps in and averts the situation enough until a worker notices the discourse and escorts the random guy out of the building. Aaron is left impressed with Hugo and decides that hanging out with Hugo on free will isn't so bad. As the two head off to a local burger joint after the incident, Ana happily declares the trip a success, and Christie is just as delighted with her, as she gets more and more invested with OPF and Ana. 

R.A - With the new success under her belt, Ana tells Anna about it triumphantly, much to Anna's nonchalant attitude. Anna is, however, slightly impressed with Ana's success and admits it to her, but very quickly regrets it as Ana gains newfound hope to become genuine friends with Anna, and starts her hijinks of friendship once again. Aaron rekindles his friendship with Ana in a more genuine way, as he advances in his friendship with Hugo enough to where he visits Hugo in the library sometimes, and Hugo joins Ana, Christie, and Anna at their lunch table. Venus and Christie get closer as well. 

Season 2

R-A - Aaron's "main friends," notice the distance between themselves and Aaron as he spends more time with Hugo instead of them, so they start to harass Hugo in private. Despite this, they and Aaron get close enough to the point where, if asked, Aaron would call Hugo a "buddy." On the other side of the coin, Ana's friendship attempts with Anna have been unsuccessful, though Anna has gotten used to Ana's presence enough to where she is (forced to be) tolerant with Ana being around her during lunch hours (She doesn't mind Christie since Christie's too busy admiring Venus, being scared of Anna or chatting with Ana, and she doesn't mind Hugo, since well, they're Hugo). 

M.P - Aaron's "friends" realize that their harassment towards Hugo has resulted in little to nothing, but didn't know how to fix the problem until Princessa, a girl from another popular group as well as Hugo's younger sister, offers to help them by constructing a plan; they will ramp up their harassment into full-on bullying, and when the time comes, they'll beat Hugo up as a warning to stay away from Aaron and people who have "actual potential in life." 

                              1. The worse the bullying gets the more Hugo tries to hide it

By the end of the second week, Aaron's "friends," corner Hugo to the back of the school and start to beat them up as Princessa mocks the sight of her sibling. In the midst of one of the friends punching Hugo in the stomach, Aaron intercedes and defends Hugo from his friends both physically and verbally. Princessa confronts Aaron about his friendship with Hugo and gives him a choice. 

 "Either stay with that freak and completely destroy your social life or come back to actual people who have been with you since day one and have done nothing but help you." 

 Though it seems like Aaron will rejoin his old friends and leave no hope left for Hugo, in a faithful moment, Aaron decides to stick with Hugo and make it clear to the group that he doesn't intend to go back to them or their soccer club (where he met these people minus Princessa). Shocked and disappointed, Princessa and the group leave Aaron and Hugo where they are, as Aaron takes Hugo to the nurse's office, and never bothers them again

R-A - Aaron and Hugo are now officially best friends, much to Ana and Christie's delight. Aaron joins Ana at her lunch table and commits to pursuing Christie. Anna tries to shut this down by telling Aaron about Christie's crush on Venus, but with their relationship already being on the rocks, Aaron takes this as competition and tries to pursue Christie. After some failed romantic attempts, Aaron sulks at Hugo's house and confides in him. Venus's father is hosting a ball for the 50th anniversary of his company and gives Venus a plus one. She invites Christie, who in turn invites Ana, who then invites Anna. Hugo, already receiving an invitation due to his family's elite status, uses his plus one on Aaron. Venus's father has also hired a tailor to make Venus a custom-made dress, and Venus offers to make custom clothes for the OPF gang, which will be finished by a week before the ball. 

Season 3

R.A - The OPF gang start the new school year with a few changes. Hugo and Aaron are no longer best friends by the title, as they now genuinely enjoy each other's company more since Aaron had spent the majority of his summer days over at Hugo's house. Anna wasn't safe from Ana's tricks of friendship, however, as Ana had stayed (mostly without Anna's permission) over at Anna's house multiple times over the summer bothering hanging out with Anna, sometimes bringing Christie along (She always has Anna's permission). 

           1.  Ana notices the strangely distant relationship between Anna and Aaron and decides to pester talk to Anna about it. Anna being Anna, doesn't want to share any personal information and tells Ana to stop poking her nose in other people's business. Ana then turns to Aaron about it and gets a joke in return. Deciding to take matters into her own hands, Ana purposely gives Anna her English journal and Anna hers when Anna asks Ana to clean up their desks (they are seated next to each other after Ana begged their teacher, Ms. Melody, to switch seats). Anna doesn't notice this change until the next day, where Ana uses it as an excuse to visit Anna's house. 

Side Plot -- Christie notices how tired Venus looks and asks her about it, to which Venus almost breaks down out of stress and vents to Christie about how her parents have such high expectations of her and it makes her feel restricted in expressing herself. Christie comforts her and encourages her to start on a small problem, then work her way up to bigger ones, one of them being how Venus dresses and refers to herself (Venus changes her pronouns to she/they)

Climax -  Venus's father's celebration has finally come, and the OPF gang all have big plans for the night. Christie and Aaron both think it's time to confess to their crushes, and, with a little push from Christie, Hugo does too. Ana and Anna, however, have some unfinished business to work through

FA - Announcing that they are now a couple, Anna, Ana and Aaron are all happy for Christie and Venus, and congratulate the two for finally getting together. Though Aaron does feel a little disappointed that it's Venus instead of him, he doesn't think it matters as much as he thought it would and quickly gets over it, as he's more concerned with his best friend, Hugo. He hasn't seen them other than in class, and even then they remind Aaron of when they first met, with Hugo being quiet and withdrawn, though it seems to be out of sadness this time. 

     1. Noticing that his attempts to interact with Hugo end in failure, he asks Christie to talk to Hugo out of frustration and slight hurt. Christie finds Hugo in a small corner in the library at lunch and tries to talk to them about their sudden distance yet nothing seems to work until Christie mentions Hugo's plan to confess. Seeing a dramatic shift in his expression, Christie immediately tries to comfort him, thinking they got rejected until Hugo blurts out how they don't want to be comforted by the girlfriend of the person they like. Confused by this reaction, Christie questions it, to which Hugo reveals Aaron's plan to confess to Christie. Taken aback by this, Christie tells Hugo that Aaron never confessed and that she's with Venus. It's now Hugo's turn to be taken aback as they ask if Aaron really never said anything. Christie confirms, to which Hugo starts apologizing for their anger and congratulates her new relationship, feeling a little happy Aaron didn't confess but is very quickly overcome with guilt from that emotion. Unsure of what to do now, Hugo tells Christie that they'll rejoin the group soon, but they want to stay in the library today out of embarrassment. Christie, still in a state of shock, nods and heads out of the library to see Aaron standing outside playing on his phone. Happy to see Christie back, he hopes for good news but gets confused when he sees her absent-mindedly walking down the hall. Aaron snaps her out of it mid-walk, surprising Christie until she quickly realizes what she's been doing and avoids Aaron's questions about Hugo because of the uncomfortableness surrounding the fact that Aaron "likes her." Aaron, confused and irritated that Christie won't say anything about Hugo, pulls her aside to a classroom and starts questioning even harder. Christie doesn't want to answer out of respect for Hugo but grows so frustrated that she blurts out her knowledge of Aaron's feelings for her and Hugo's feelings for Aaron. Shocked by this confession, Aaron doesn't even notice that Anna and Ana are both standing at the doorframe, both with a look of horror on their faces. Time seems to go too slow yet too quickly for a moment as all four of them try to say something until they're disturbed by a familiar voice. They all turn to the hallway to see Hugo, standing there, books in hand, and a confused expression on their face. 

2. After what happened, all Aaron could think about was Hugo's feelings, and it doesn't get better when Hugo rejoins the group. Unsure about what Chrisite told him, he plans to meet up with her to talk about it. Uncomfortable about meeting up with him alone, Ana tags along, much to Aaron's surprise. Before they talk about Hugo, Ana asks about Aaron's feelings for Christie. Aaron admits to his once-had feelings but explains that it didn't matter much to him anyway. Christie questions this to which Aaron responds that when he heard the news of Venus and Christie getting together, Aaron wasn't all that hurt. Ana pushes this further by asking for more details, how long he's liked her and why, to which Aaron answers the questions easily, though the answers confuse Ana and Christie even more. His elicit feelings were long-term, yet he only liked her for her kindness, and thinking about her with someone else doesn't bother him. Connecting the dots, Christie asks how he feels for Hugo, and why he likes to hang out with him. Aaron, confused with these questions but tries to answer them anyway, gets a little stumped. But when he does come up with answers, they're a lot vaguer. He started hanging out with Hugo because he seemed to be the only person around him who wasn't fake, but now that those fake people are gone, he still hangs out with him for an unknown reason other than Aaron enjoys his company. So much so that he'd much rather prefer to hang out with Hugo all day than do anything else. Ana, now connecting the dots herself, prompts the question of "maybe you weren't bothered by Christie's relationship because you already had one." Aaron is taken aback by this, and as his face flushes, he's unsure what to think. Feelings for Hugo? No way. But as the week goes by, he notices every little thing about Hugo and what he does and is shocked by how he already knows Hugo's mannerisms so well. The thought of him liking Hugo becomes less and less extreme until he admits it to himself with Anna's help (teasing) throughout the next two weeks. He likes Hugo. 

RA- As the end of the year approaches, the start of Aaron wanting to be with Hugo does as well, and he plans to confess to Hugo at the end of June. 

       1. Aaron sees Hugo's increasing relationship with Ian and gets very insecure about it. The more time Hugo spends with Ian the less he does with Aaron. To make up for not being able to hang out for the past few days, Hugo invites Aaron to chill with him in the library after school. Aaron, a little too happy to receive the invitation, agrees and looks forward to it all day. But before Hugo can head to the library, he's stopped by Ian, who needs help with an assignment for class. Unable to say no, Hugo helps and is in turn late to the library. Unbeknownst to him though, an excited Aaron had gone to the library earlier than planned to pick out some books for Hugo and set up a little area with a bean bag, a blanket, his phone for music, and some snacks with drinks. But by the time Hugo arrived, Aaron was full of anxiety that came out as anger. Unable to hold back his jealousy any further, Aaron lashes out at Hugo in the middle of Hugo trying to explain what had happened and leaves them in the mess of snack wrappers and fallen books. Shaken and broken by what just happened, Hugo exits the library to find Ian waiting at the school gates. Ian approaches Hugo and asks him out on a date. Hugo doesn't know how to respond, but after what had just transpired, thinks the best way to move on might be to shift focus onto someone else and says yes. 

       2. Ian takes Hugo to a local fair for their date, and they spend the day riding rides, winning stuffed animals, eating nasty food, and all-around having a good time. Before Hugo has to go back home, Ian takes them on the Ferris wheel and makes small talk that turns into talks about their past. Hugo talks about their home life and how they've been alone their entire life for the most part, until they met ... Ian sees the sadness in Hugo's eyes as he knows who Hugo's thinking of, and takes Hugo's hand to say that maybe he can help Hugo feel less lonely. Hugo knows that this is the perfect opportunity to move onto someone else as Ian leans in for a kiss, but all Hugo could think of at that moment was how much more perfect it would be if Ian was Aaron. In the end, Hugo can't do it and the two get off the Ferris wheel. Before Hugo goes home, Ian gives Hugo a stuffed bear he won and tells Hugo that his heart is always open for when Hugo is ready. Hugo thanks him, and heads home, ending the night in tears and guilt that he couldn't kiss Ian.