Oh ho ho what a highly interesting question, anon👀
(Answered under the cut because it's a bit long)
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Before I give my proper answer, allow me to explain a bit of my interpretation of Tails. I actually see him as a sort of naturally jealous person with some innate possessive tendencies who has grown used to curbing these tendencies of his, which he had to do due to a number of factors.
One major reason is due to Sonic himself. To me Sonic has always had a complicated relationship with different kinds of love or attraction (and I do see him as on the aro/ace spectrum). So, when absolute strangers (or those he doesn't particularly like) obsessively pursue him for clear romance/possessive reasons, he tends to react with strong rejection or indifference, in contrast to how he welcomes ego stroking and praise from those who can be merely categorized as "fans" (or those he does particularly like). To me, Tails' initial admiration and pursuit of joining with and becoming like Sonic very well parallels how Amy Rose began to admire and pursue a romantic relationship with Sonic. Even if we consider that Sonic did save Tails that one time from being bullied (according to Sonic Prime and a new animation for Sonic 2 present in Sonic Origins), his pursuit of trying to work together with his hero (which is detailed a bit more in the jp manual for Sonic 2, and includes Tails going so far as to follow after Sonic everywhere and modify Sonic's plane) really isn't any more "normal" than how Amy begins to pursue a romantic relationship with her hero after Sonic saves her from Metal Sonic. The only real differences here were that Amy was explicitly pursuing romance, and that Sonic rejected Amy's advances but eventually took Tails on as his sidekick/little buddy.
This is also not to mention the implications here and there in what we can find of Sonic and Tails' backstory that Sonic would continue to run away and pretend he did not care, while secretly keeping an eye out for Tails.
And beyond that, as one of Sonic’s oldest friends, Tails gets to spend a lot of time around Sonic, and gets to see firsthand how he reacts to romantic prospects, his complicated relationship with "love" as a concept, and is present as Sonic’s group of friends steadily grows.
With all of that, I at least see Tails learning to deal with his innate jealousy and possessiveness so
Sonic doesn’t reject him
Because he doesn't want to keep Sonic from pursuing relationships with others
And for the sake of one's image/being a good person
If Tails has learned that confessing and making his romantic intentions clear could lead to Sonic rejecting him or it ruining their friendship (since he's seen first hand how Sonic has reacted in certain cases to love confessions or overt romantic affection), it makes sense to me that he would try to hold his feelings back (both those that are not squarely platonic and are explicitly romantic and/or sexual). And when it comes to Sonic, there's a guilt factor and an impossibility factor when it comes to keeping him from other people. Not only would Tails feel at least a little bad for restricting him, but Sonic does not respond well to being controlled. Now of course, how he reacts does depend on the time of his life and who it is, but there is nevertheless a futility in trying to control Sonic "I have no master except the wind that blows free" Hedgehog. And finally, my view on both Sonic and Tails, well... I believe that image and visual alignment is a big thing for these two, and that the two are secretly more...in the gray (or at least, that they're surprisingly immoral so to speak). In their origins to me, Tails is just a kid, minding his business, who does not inherently seek to hurt others (though his faith in those around him does matter), and Sonic is just a kid, free as the wind, who doesn't particularly care about being a good guy, but loves the attention. Essentially, though he does save some people on whim, the idea is that Sonic originally fights Robotnik simply because the Doctor, his machines, and his pollution have such a negative effect on his home. So beyond this point, he fights as a hero both out of interest of having his home intact/being alive, and because (simply put) he likes what comes from being considered a hero (all the praise and perks). And so because Sonic is someone that Tails admires, because Sonic has to uphold a baseline image or reputation so he can still be considered a hero/good guy, Tails becomes accustomed to doing the same. That's a bit of an oversimplification (how I see them and why is the subject of a proper essay about that), but the point is that Tails is also conscious that trying to overtly control or manipulate Sonic would not objectively be considered "hero or good guy behavior", especially if it goes too far.
And so with all of that plus the fact that Sonic has never seemingly accepted anyone's romantic inclinations or dated anyone, Tails curbs his natural inclination towards jealousy and possessiveness so he can be content enough to be at Sonic's side. Perhaps there are more friends Sonic is going to get, people he's going to show an interest in, but Tails can put stock in the fact that it's unlikely that Sonic will date anyone. Plus, even if that somehow does happen, Tails is largely fine as long as he's guaranteed to be by Sonic's side no matter what. So as long as he can be with Sonic forever, no matter their relationship, he's as content as can be.
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But then Sonic starts dating Nine, right?
And hahaha don't get me wrong here. Tails is pretty practiced. He's not gonna blow up or anything.
But once he gets past the initial shock of that being true, I think he just feels jealous and conflicted by default. I mean, he's just been accepting that there's no hope of ever being in that kind of relationship with Sonic. And not only has someone gone and done it, it's not just anyone.
It's a version of him.
And if a version of himself managed to do it (a version of himself who once lashed out at and fought against Sonic no less), then what does that mean about him? Does it mean that there's something about Nine Sonic likes better? Does it mean that he's had this entire situation wrong? Does it mean he lost his chance and he'd been so afraid for nothing? Does it mean that he could have had that this whole time?
And that's not to mention navigating this. Even if I believe Sonic is very very capable of having multiple best friends or even partners, it's only natural for Tails to get a little afraid of being replaced (especially if he learns that Sonic also considered/considers Nine as a best friend also)
But Tails is the type to not want to burden Sonic with all of this while becoming increasingly more worried. And although he would naturally have a complicated relationship with Nine, I still think he would generally like him and not want to take out his feelings on him. So with that being said, I think he'd sort of try to hold it in and act normal while really not acting all that normal, because though he could hide his feelings better if he wanted to, he still kind of lets it slip because he kind of does want to talk to Sonic about it or let his feelings be known.
I think that whenever Sonic eventually does see that Tails is acting a bit off he'll eventually talk to him about it or try to get him to, but, honestly, even if Sonic could say things (true things) that would make him feel better, I don't think Tails could be as content as he would be if it was idk... Knuckles or Shadow or what have you. Because if it was anyone else, Tails could be more content knowing that his relationship with Sonic is special and that he'll always be by his side, even if he's dating someone else.
But with the fact that the person that Sonic has chosen to date is another version him—a version of him which Sonic has also kind of clearly developed a similar "best friendship" with? I feel that even if Sonic tries to reassure him, Tails will forever be plagued with bitter and jealous feelings. Even if he'd never force Sonic to stop dating anyone, much less force him to date him, I don't think he can even really feel content here unless Sonic chooses to date him also if that makes any sense.
So, yes. That's my answer. Tails would try to be really good about it, but he's still bitter and annoyed and jealous and wondering if he's enough or has been doing something wrong. He's wondering why it couldn't have been him. And he won't be able to just be content at Sonic's side if he can't also be with Sonic. So while I can't say how long it will take, something will have to give eventually. I think at some point in their future, Sonic will have to tackle his specific feelings for Tails and they'll have to talk about their specific relationship, especially if he's dating Nine right in front of him.
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Fun fact: if you take on the Paldean Gym Leaders in the objectively best order (which I didn’t in either version oh well) the genders of each pair of Kalos Gym Leader and Paldean Gym Leader are the same in each version - the first (Viola and Katy), third (Korrina and Iono), sixth (Valerie and Ryme) and seventh (Olympia and Tulip) gym leaders are female and the second (Grant and Brassius), fourth (Ramos and Kofu), fifth (Clemont and Larry) and eighth (Wulfric and Grusha) gym leaders are male. In addition, out of the five pairs of gym leaders between Kalos and Paldea where they share a type, three of them are in the same spot based on this order (Bug-type Gym Leaders Viola and Katy are first, Psychic-type Gym Leaders Olympia and Tulip are seventh and Ice-type Gym Leaders Wulfric and Grusha are eighth). And as a bonus the second gym leaders both have cool hair that matches their types well. And the Grass and Electric gym leaders are always next to each other in that order plus the Grass Gym Leaders are among the oldest gym leaders of their region (Ramos almost certainly, Brassius probably younger than Ryme and maybe Kofu) and the Electric Gym Leaders are among the youngest gym leaders of their region (Clemont is around the same age as Viola, Grant and maybe Korrina but probably the youngest between them, Iono definitely). Oh yeah also the Psychic cities both begin with A and the Electric cities both begin with L
The first fact means that both regions have an equal gender ration for their gym leaders. In addition, they both also have equal gender rations for their Elite Four members (I believe they’re the only regions where both of these are true all the time so far though I might be forgetting something. Alola and Galar automatically don’t count because Alola doesn’t have Gym Leaders and Galar doesn’t have an Elite Four. Kanto, Hoenn and Unova are also probably excluded because they all change their lineup at some point (although it doesn’t change the gender ratio in Hoenn but then they also have Tate and Lisa so that overcomplicates stuff too. It also doesn’t change the overall gender ratio in Kanto but it does change the individual ones for Gym Leaders and Elite Four members)) although only the first and third members line up if you take on the Kalos Elite Four in order. Also both regions have female champions (and the only reason the fandom doesn’t consider either to be their least favourite is because no one can remember Trace 😭 justice for Diantha, Geeta and Trace! And by that I mean from the fandom, not Game Freak. It’s not Diantha’s fault she was too busy to beat Team Flare and kick them out of Kalos for good, Geeta’s fault she decided to make her ace a Pokémon that should be sent out as soon as possible just because she loves it so much or Trace’s fault he doesn’t want to get himself and you imprisoned for starting a physical fight only to plead innocent so only the player gets locked up (yeah this is something I think RGBY era Blue would do)) and because Larry takes a spot as both a Gym Leader and a member of the Elite Four that means Kalos has a slightly more even gender ratio for its league overall but both have more women than men. Additional fun fact (yep, I love comparing Kalos and Paldea and PLZA just gives me a bigger excuse to do it) - Kalos makes you take on the Gym Leaders in order but allows you to take on the Elite Four in any order while Paldea allows you to take on the Gym Leaders in any order but makes you take on the Elite Four in order. Oh yeah also there’s a Steel-type Elite Four member in both regions and both regions end their Elite Four with a Dragon-type trainer
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listen in my head there’s like, a slightly au version of canon slightly to the left where after joe leaves hermitopia and the enemy of the state thing happens he’s a bit more bitter about it and then e!false hires him and instead of it being one temp job he ends up just permanently being a citizen of cogsmede and. okay maybe he’s betraying the hermits a little—a lot—but they accused him of doing it first, is the thing. he hadn’t actually betrayed anyone, he’d just decided to leave, and they labeled him a traitor and a coward. so when e!false asks, if he starts telling her whatever she wants to know and also more—well, it’s only what he was already supposedly doing, he’s just… actually doing it this time. and we go from there. joe and e!false bond over sort of being outcasts.
and then if I’m REALLY self-indulgent with this canon to the left. joe is also cub’s friend and is willing to vouch to bring a (somewhat possessed) cub into the fold; he’ll just clean up if he does anything dangerous around cogsmede. elsewhere, though, is perhaps fair game,
and like. idk where this is going. but I’m just saying that somewhere in my head this only very slightly nudged version of events exists where joe is slightly more bitter and even more removed from the other hermits and also he’s with my empires blorbo,
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Gah those who say simblr are dead should go and consume the hundreds of posts by storytellers or game players and get excited or attached so they can look forward to updates. It’s unfair that because new content isn’t being continually uploaded daily it’s deemed as dead. There’s also so many people who post text updates about their days or lives. There’s so much more life in this community besides a new edit being dropped daily to look at! Or go find new blogs! Get out of your comfort zone guys! This community also has waves of activeness and quietness which is normal for the summer time. (Sorry, I’m not ranting at you, I’m hoping that maybe people will realize that this is nothing new and to stop worrying themselves over it.)
i totally agree anon! tbh i do have sympathy for those who say this, because i totally remember having this same concern in earnest years ago when simblr first had a massive dropoff from the activity i was used to seeing in 2018. but it's kinda funny now, after so many years have passed and people are still saying the same things about how simblr is dying when it very obviously hasn't died yet haha. this is just the level of activity it's been at for a while now, but that doesn't mean it's dying, it's just being maintained at a different rate than it was back at simblr's peak activity (which again imo i'd say that was around 2018). there's always people posting on some corner of simblr about something, whether that's story posts, gameplays, edits, or even just answering asks or making text posts abt their days. you just gotta explore your options and follow as many simblrs as you can yk!! it's unreasonable to assume ppl are gonna post "content" every day (remember that this is just our hobby and not a full time job lol), but the community is still definitely here nevertheless
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