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Blood Brandy

@Takashi.0  
If Tails is tall enough to look human Twilight in the eye, it’s probably safe to say he’s aged up (Which no one ever seems to think of when Tails is in a pic, for some reason)
Background Pony #DFDF
Come to think of it, Tails actually looks pretty down at being rejected….
 
Suddenly, I have a weird headcannon of Tails having a crush on Twilight but is too shy to do anything himself, meets Dash through a mutual friend (CoughSonicCough) and she’s trying to help a buddy out, only for him to get shot down because of his species, and Dash chewing Twilight out over it after tails leaves in tears…
wselfwulf
Artist -

Spoony Bard
@Beau Skunky  
yea it’s part of a series of pics that artist has done where each one of twilight friends try pair here up with a date. the best one is applejack’s one, BATMAN.
Beau Skunky
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Cool Crow - "Caw!" An awesome tagger
Magnificent Metadata Maniac - #1 Assistant
Artist -

Stuffed animal
@wselfwulf  
Ohhh I misinterpritated it, I thought Dashie was the one dating Tails. (She was introducing Twilight to her date?) Though, seeing how the artist on DA left no description, it’s hard to tell.
 
It’s weird even Sonic-haters like the other Sonic characters. :P
Beau Skunky
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Cool Crow - "Caw!" An awesome tagger
Magnificent Metadata Maniac - #1 Assistant
Artist -

Stuffed animal
Am I the only one who finds it funny/odd this has fewer downvotes, and more upvotes then nearly all the “Dashie X Sonic” pics? (I guess ‘cause the “shipping” is more subtle in this one, and played for laughs.)
 
I’m curious why “Human Dashie X Tails” is somehow a “more acceptable pairing?” :P
Blood Brandy

@Psychopomf  
Twilight:He’s a Fox!
 
Tails: Yeah, he’s a fox who’s smart enough to understand you and who has feelings (Walks off)
 
RD: Great job, Twilight, do you know how hard it is to find someone as smart as you who isn’t old as dirt?
RogueBadnik
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Non-Fungible Trixie -
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!

⌜Ω⌟
@Beau Skunky
 
Yeah, he is one of my favorites voice actors of Tails. I find that Tails kinda cute and adorable.
 
I don’t know why there was no Tails in Underground. I know thaa was another universe (Actually, in a comic, the Archie Sonic traveled to the Underground universe, just to find very funny that he was a prince in that world and Tails doesn’t exist there.)
Beau Skunky
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Cool Crow - "Caw!" An awesome tagger
Magnificent Metadata Maniac - #1 Assistant
Artist -

Stuffed animal
@Shadow_the_Hedgehog  
Yeah, that one was kinda adorable. Funny thing is, an actor named Christopher Even Welch (the same name as Tails’ actor in that show) passed away a year back, and people mistook him for the AoStH Tails. (He would’ve been in his 20s when voicing Tails in the 1990s, if he did, and Tails sounds voiced by a li’l kid in it.)  
It turned out the one who was Tails was a different Christopher Even Welch, and a younger one to.
 
Wonder why there’s no “Sonic Underground” Tails. (Did Robotnik eat him, or something?)
Beau Skunky
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Cool Crow - "Caw!" An awesome tagger
Magnificent Metadata Maniac - #1 Assistant
Artist -

Stuffed animal
@Background Pony #7950  
By that request, does that mean when talking about “Sonic X,” does that mean we have to call him “Sonic X Tails?” Or for the other canons “SatA.M. Tails,” “STC Tails,” “OVA Tails,” ect?
 
There’s more Tails then just the game one, and Archie one. :P
Background Pony #67C7
When talking about Archie Tails, make sure you’re calling him Archie!Tails.
 
The default Tails is the one from the games; I don’t care how much you love Archie Sonic.