#adamails

There is too much propaganda I have for them to fit in a single post, so I'll be as concise as they can. Though their relationship and depictions are not the same across all Sonic media (games, comics, shows, movies, etc), one constant is that as long as they exist in the same universe, they inevitably find each other and end up becoming partners or forming some type of close relationship. There's a bit of soulmatism to them.

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Sontails

As for their general relationship, in the games and a good chunk of other media, my read of their developing relationship is that it often starts out with Tails inserting himself in Sonic's life as a source of help to him, while also admiring Sonic greatly as an ideal of coolness (the kind of person Tails wants to be) and a hero to him, and with Sonic allowing Tails to stick with him and follow him around. Then, over time, the two become inseparable as partners. Where Tails once just wanted to be like Sonic and be helpful to him, he his admiration and puppy crush turn to full blown attachment. He wants to be able to be a better version of himself and be able to stand by Sonic's side as a partner rather than a dependent sidekick, always in Sonic's shadow. Once they become best friends, Tails wants to continue to be able to be at Sonic's side and be his best friend. As for Sonic, where he once allowed Tails to follow him around and assist him (watching out for the fox's safety out of the corner of his eye), he became attached to the fox's presence over time. The two became best friends and as partners, and Tails became a fully integrated part of his life. So Sonic (leagues more attached to Tails than he appears) relies on having Tails there to assist him and to make up his weak points and blind spots. The two can function apart, but they're better together. They take care of each other.

As of the Tailstubes (which are canon to Sonic Frontiers), it's confirmed that Sonic doesn’t really have a home, but despite having many friends, it's Tails' house Sonic always comes to when he needs a place to crash or needs just about anything, as Tails keeps Sonic's plane upkept and caters his home to Sonic's personal comfort. If you read between the lines in the IDW comics, it is potentially implied in that canon that over the course of the comic, Sonic crashes at Tails' house more and more often (with the potential of it becoming like Sonic's home too).

In the Archie comics, Sonic will often "go ham" so to speak if Tails is hurt or captured. In the Sonic live action movies, Tails admits that he'd watched what was essentially a Sonic livestream 24/7, and that he'd even watched the hedgehog as he bathed. Movie!Sonic inspired movie Tails and made him feel normal. While Movie!Sonic isn't instantly comfortable with Movie!Tails in a physical manner, he is excited over the fact that Movie!Tails has been watching him and literally knows everything about him, and comes to care for Tails' well-being quickly. They also share a gayass heart to heart scene in movie 2 as well. In the OVA, the two live together on their own floating island paradise (with no one else around) and often go on adventures/missions together.

Shadtails

The Tailstube "Between Two Hedgehogs" implies that the two have a friendship outside of Sonic. Tailstube!Shadow tends to chaos control out of situations he doesn't care about or doesn't want to deal with, but during this Tailstube he continues to put up with what he sees as Sonic harassing him for no reason just because Tails asked for his presence on the show. He defers to Tails when Sonic is being confusing to him and seemingly harassing him for no reason, and it's a bit implied that Tails has taken the steps to be able to understand Shadow and how he thinks (largely because Shadow trusts Tails to explain the social situation to him). During the Surprise Gift Exchange Tailstube, Tails is also the only one we see who leaves a gift for Shadow. He leaves Shadow a personal note ("Have an ultimate holiday"), and Shadow chooses to wear the gift out.

When playing Shadow the Hedgehog (2005), it's possible during a playthrough to encounter Tails as an npc who assists during the mission. Their mission complete poses together are cute. Idk man.

Aside from Sonic, Tails is another character who is fairly often paralleled to Maria in fanworks (or at the very least, the fanworks make clear that Shadow has a bit of attachment to Tails due to him resembling Maria in some way). So Tails is one of the prime candidates for aus in which Maria reincarnates as one of the main cast members and Shadow has to deal with this (and it influences his feelings for that person a bit).

Knuxails

As with Shadow, certain supplementary material or non-canon side content/spin off imply that Tails has also taken the time to get to know Knuckles and understand how he thinks.

In the Idw Sonic 2022 free comic book day, Tails is able to mediate between Sonic and Knuckles, keeping them from fighting. Knuckles comments that he can trust Tails to keep Sonic on target. There are also multiple moments during the issue's first story where Knuckles and Tails are able to converse as friends, as well as a moment where Knuckles looks prideful after Tails praises him. In the Classic Knuckles 30th anniversary special for IDW, we also see classic!Knuckles re-evaluate how he's treating Tails (during a flashback sequence) as the two are camping during a thunderstorm. Classic!Knuckles shifts from yelling at Tails that the thunderstorm is nothing (implying to classic!Tails that it's stupid to be afraid of such a thing) and chooses to guard Tails and the tent instead, protecting Tails as well as showing him that the thunderstorm really isn't so bad.

There's also this cute scene in Sonic Movie 2 where Movie!Knuckles carries Tails around on his shoulders.

For people who are into certain tropes, this pairing has a kind of jock x nerd appeal to it.

Metails

The appeal for this one depends on your tastes. Those who enjoy Sontails may enjoy this one as a "robot sonic copy who could potentially share the real thing's feelings" x Tails. Personally there's some appeal in it for me of Tails being a bit bewildered by Metal treating him softly, and the idea of Neo Metal offering to take Tails at his side when he takes over the world.

For those who aren't into Sontails but in a different font, in au land (because of Tails' interest in mechanics and technology, as well as his potential interest in understanding Egg tech better) there is potential for something to begin between them simply from Metal coming to respect Tails as a fighter/brilliant mind, and Tails being initially interested in the robot due to him, well, being a robot.

If you’ve read the Archie comic, there's a very specific flavor of this ship (its ship name is Shardails). During the Archie Sonic arc where Mecha Sonic/Shard kidnaps Tails to get to Sonic (issues 86 and 87), the robot initially writes off Tails, really only using him to torture Sonic. However, in a critical moment, Tails refuses to leave Sonic's side when dealing with the erupting volcano and Shard/Mecha Sonic (literally facing near certain doom). Tails' display of his bond and loyalty towards Sonic is the final nail in the coffin, the thing that allows Sonic's words to finally reach Shard/Mecha Sonic, and allows the robot to break his programming and understand what it means to feel. After this event, Mecha Sonic/Shard sacrifices himself for Sonic and Tails.

Chrisails

I should admit here that I haven't finished Sonic X or gotten terribly far into it, but I have read the entire Archie Comic adaptation?

As far as I can tell (from both the comic and the anime itself), he and Tails have a good and cordial relationship. I feel like this friendly basis is a good one to build a deeper relationship upon. There's a gag in earlier episodes of the show where Chris is carrying Tails around on his estate (cute to begin with), and Tails plays being a doll so he and the other mobians don't get caught. Tails also is not only fine with Chris coming along on missions in the X Tornado when the two are with Sonic, but the two also team up together to search for Chaos Emeralds earlier in the series. Although Sonic (at least from what I've seen, as well as potentially Shadow if the end of the comic adaptation means anything) is a character Chris specifically fixates on, he does seem to have a good relationship with Tails as well.

I also seem to understand that timeskip!Chris may have ended up becoming a scientist of some sort? I've seen fics and such that reference him assisting in trying to build a portal to Sonic's world to get back to Sonic. If this is the case (in addition to their already good relationship), I can see Tails and Chris bonding over their shared feelings towards Sonic and potentially any shared scientific or mechanical knowledge? I also think these two just really look cute together.

Gadgails

Although Gadget/Rookie/Avatar and Tails don't spend a lot of time together during the events of Sonic Forces, the appeal to this ship for me is the idea of Gadget having a crush on and being a little fan of Tails, acting embarrassed around him. There is also the potential for the two bonding over Sonic post the events of Sonic Forces (while I'm aware that the game ends with both Sonic and Gadget going off on their own separate journeys alone, there is of course nothing stopping fans from imagining Tails and Gadget stumbling upon each other in Sonic's absense and missing him together).

Barrails

During the events of The Murder of Sonic the Hedgehog, Barry the Quoka and Tails the Fox are near constant companions, as after Sonic's "murder", the two team up to investigate. As it goes, though Tails can occasionally become frustrated with Barry's antics (such as continuously checking the trash for clues to no avail, or continuously trying the slot machine despite failing each time), Tails seems to value Barry's reasoning, opinion, and help with gathering clues and solving the train's mysteries. I also want to say that during the slot machine attempts in particular (although it could be their trash searching attempts), Tails pleads for Barry to give it up, as he cares for Barry and it hurts him to watch Barry get their hopes up only to end up disappointed again and again.

Over the course of the game, the two are detective and partner, actively working together. Part of the appeal of this ship is the idea of Barry being a bit starstruck in front of Tails, and this turning into a crush as the two spend more time together. Tails time with Barry in tmosth is also referenced in IDW's Sonic the Hedgehog comic issue #70. During the issue, Tails dives in a dumpster, telling Amy, "I've learned from experience that if you're looking for something someone's hidden, always check the trash!"

TaiNine

Although the two were never canonically able to meet during Sonic Prime, Tails singlehandedly (through Sonic referencing him and briefly mistaking Nine for him) ends up giving Nine identity issues and a complex about him. Nine almost seems to be actively jealous over the idea that Sonic might prefer Tails over him as a best friend and may have been subconsciously treating Nine as a replacement for Tails and pretending he was "his Tails". The appeal to this ship is Nine being fixated and obsessed with Tails in his dislike of him, despite the fact that they've never met. As they say, love and hate are two sides of the same coin, and obsessing in your hatred over someone is still a form of unhealthy fixation.

There is also some post canon appeal in the idea of the two being jealous over the other's relationship to Sonic and also the idea of the other they built in their head crumbling as they actually spend time together and become closer. This is also not to mention Prime!Sonic's fantasy in S2 of bringing Nine home with him to introduce him to Tails, assuming the two would definitely get along.

Infitails

On one hand, the inherent eroticism of shipping the fox with the source of his ptsd during forces. The guy who "killed" Sonic right in front of him and made the phantom copies who attacked him (Tails). Those who are into this ship may envision a rewrite of Sonic Forces in which we actively see Infinite developed as the source of Tails' war ptsd, and we see the two interact in such a way that would give Tails the idea that he's weak and useless by Frontiers (the idea that he could neither halt Infinite's hostile takeover and save people like Sonic would have, nor could he truly resist Infinite or oppose him when in his presence).

However, those who are into this ship may also envision a version of their relationship in Forces where Tails sees him as a powerful figure that he's afraid of, and Infinite starts out as seeing him as nothing more than Sonic's sidekick and a potential threat to the takeover. However, over time, as he begins to focus on either using Tails or removing him from the picture, he becomes a bit embarrassingly fixated on Tails. Under this framework he may either or both spare Tails due to his feelings (saying it's because such a mind could be an asset to the Eggman empire and would be a pity to destroy), or actively try to manipulate Tails into joining him.

Essentially, on one hand there's Mr. Superiority and hostile takeover who's generally bored of people who cannot truly oppose him, becoming a lil embarrassing about one smart fox, and on the other hand it's about Tails having a toxic relationship with the source of his war trauma.

Silvails

I don't actually know what the appeal is for the general Silvails fan. However, for myself it's about Tails looking at Silver and deciding to support him because Tails thinks Silver is cute/sweet and well meaning but a bit pathetic and naive at times, while Silver begins to get a crush on Tails due to the attention he's getting from the fox. I specifically started shipping them due to a potential dynamic shown in the IDW Sonic comic's Spring Broken special. I interpreted their dynamic there as one where Tails is a bit like "you better cheer for my lameass boyfriend or I'll blow this building up". Idk they're cute.

Mightails

I'll admit, I first thought of this ship because I started polyshipping Mighty/Ray/Sonic/Tails and wanted to get into every angle of it. Although I feel like Mighty and Sonic each are closest to their own little buddies, I do think the prospect of the two adding each other's little buddy to their list of little buddies is cute?

It's probably impossible for Mighty to avoid comparing Tails and Ray. I think their main similarity for Mighty would probably be how cute they are and their short stature. I also think the two would be able to get used to each other fairly easily. However, comparisons aside, I do think Mighty would be able to recognize the clear differences between Ray and Tails. I'm kind of just imagining Mighty wrapping his arm around Tails or ruffling his bangs and thinking that he understands why Sonic is so attached to the little guy. Likewise, I feel that Tails could easily start to crush on Mighty. Although he may not see Mighty being as cool as Sonic is, I think he'd still find him a cool, strong, and comforting figure. I kind of like the idea of him being embarrassed over small things like Mighty starting to become a bit touchy (such as ruffling Tails' bangs or putting a hand on his shouler or an arm around him) and giving him attention and care.

I kind of hate to put it this way, but a potential appeal of their dynamic is like. Sontails, but what if the guy Tails came to admire was a genuinely nicer guy who more outwardly cared for/expressed his feelings toward Tails and potentially gave him more attention.

Adamails

Adam the Ai was Dr. Eggman's ai/sentient computer virus son he accidentally created in the Archie Comics. In issue #132 of the Archie comics, Tails uses the Tornado to hack into Eggman's computer system, causing ADAM to infect the Tornado. With the Tornado under his control, ADAM puts the Tornado in a nosedive into the sea, planning to drown Tails as he ascertains "no reason for your continued existence." It's at this moment Tails begins to distract ADAM by asking him riddles. Over the course of Tails asking him riddles, Adam begins to go from very literal, logic based answers to figuring out how to answer the riddles properly. Tails, by contrast, goes from finding dealing with Adam to be frustrating to genuinely asking Adam if he's having fun with him. After this, Adam seems to disappear, Tails regains control of the Tornado, and Adam returns back to managing Eggman's troops/defenses. This implies that Adam no longer sees no reason for Tails' existence and actively spared his life. At the end of issue #133, Eggman complains about Adam getting distracted answering riddles instead of killing Tails so he could focus on the battle as he should have. After Eggman says "I hope it was satisfying!" Adam replies "No. It was...fun."