Staticshot relationship meme!! Their relationship is complicated bc they can never make things easy, but I think this sums things up pretty well! (at least before they break up for a little in s2e4)
Closeup of their portraits too! My sillies 💕
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Staticshot relationship meme!! Their relationship is complicated bc they can never make things easy, but I think this sums things up pretty well! (at least before they break up for a little in s2e4)
Closeup of their portraits too! My sillies 💕

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Cupid Lore!
Just a little explanation about the Cupids, written by yours truly uwu. Ask box will be opened for inquiries as well, should you have anything you're curious about~Mila💟
So, why are the cupids called Cupids? On one hand, it’s a simple answer, but on the other I feel a need to explain in detail. The cupids are a humanoid alien species with intense love energy. This overabundance of love energy doesn’t affect members of their own species quite like it does others, though. Members of other species can’t help but feel drawn to the cupids, be it sexually, romantically, or platonically. It’s not intentional on the part of the cupids, mind you. There is a part of the species that holds an innate charm that simply draws others in. It could be because of their looks, their voice, the conversation you just had with one. Their love energy is very soft and warm. This is the side that Mila comes from.
Gregoria’s side fits more with the stereotype you commonly see with cupids and cherubs cycling throughout the universe, as their love energy is more chaotic, warranting the creation of weapons they use to channel and focus said love energy. It’s not in the way that you’ve come to associate with cupids, though. The weapons don’t force you fall head-over-heels in love with someone, they just force you to come to terms with your feelings. It could make you drop your pride and finally apologize, because deep down you really were sorry for whatever it was you did; it could also assist in the relief of sexual tension (Disclaimer: there is no control over where the sexual tension is taken out, we cannot guarantee that it will always be done in privacy).
These two types might not always get along, but in the case that they do, they’ll team up. While this team up does not always start romantic, it does tend to end up that way.
Additional Notes:
These two particular cupids are called Cybertronian Cupids or Cybertron’s Cupids because of their tendency to be drawn to Cybertronians. They saw giant robots and decided they wanted to hang around them, help them out in more ways than one.
Gregoria and Mila are a couple, but that makes them no less inclined to share their overabundance of love with others they find themselves drawn to. A decent number of their partners are mutual, but not all of them are.
Gregoria’s common love weapons of choice are her heart paddle and love bombs. Love bombs being the more potent and also more likely to accidentally effect more than just their intended targets.
Supernatural Free Thinking -- What’s the Deal With Cupid?
Welcome to another Supernatural Free Thinking session. Wherein, I think about a random element in Supernatural and try to sort out how I feel about it -- all in an attempt to help make the show make a little more sense.
What’s on the docket today? Well, let’s talk about cupid and cupid’s affect specifically on John and Mary’s love life. I’ve often seen this pop up within the fandom. Do cupids force you to fall in love? Were what John and Mary felt for each other their actual feelings or were those feelings manufactured as a tool in birthing Sam and Dean? Both Heaven and Hell were definitely invested in making Sam and Dean happen. And it is canon that the match between John and Mary was cupid-influenced. So did John and Mary ever really love each other?
Well here’s my take on all of this. First off, when talking about cupid lore within the show, I don’t believe that when you get hit by cupid arrows, it forces you to fall in love. Why do I think this? Because Chuck specifically gave humans free-will. When heaven uses humanity as their tool to conduct their business, they have to operate within the constraints of freewill. Angels cannot possess humans without that human’s expressed permission. Heaven has prophets but those prophets still operate under freewill. Prophets have to choose to relay the information they receive. Now granted, Heaven can and will coerce humans to work for them if it’s necessary but it technically doesn’t really break the freewill protocol. Chuck isn’t in the business of dealing with “shades of grey,” he deals with absolutes. His sister was causing problems for him so he locked her away instead of trying to work with her. Lucifer was becoming problematic so he got the boot, too. Humanity started to disappoint Chuck so he walked away. Looking in-between the lines and compromising is not something that’s in Chuck’s nature. So while there’s definitely something to say about angels coercing humans and a legitimate argument can be made about whether or not a decision made from coercion can be considered freewill, according to how Chuck initially created freewill, regardless of what’s happening, it’s still our decision to make the decision we make. If the angels threaten to kill everyone you love unless you say “yes” to becoming a vessel, while a douchey move on the angels’ part, it’s still your decision to say “yes” or “no”. It’s still your decision on whether or not you’ll let everyone you love die. That’s your freewill. That’s what Chuck gave humanity. I mean, if you’re under the influence of alcohol and you kill someone while you were under the influence, the fact that you were inebriated doesn’t absolve you of wrong-doing, does it? Same basic principle can be applied here. Regardless of events that lead to that decisions, it’s still our decision to make the decisions we make. That’s freewill in its most basic form. So, no, I don’t believe cupids force people to fall in love. That would effectively take away their freewill and cupids are the tools of heaven. They can’t do anything that takes away that basic freewill.
So the next question to think about is: What do the cupids do then? Well, I’m about to go a little old school on you and reference some cupid lore that popped up in Xena: Warrior Princess. In that show, Cupid could get two people to fall for each other by firing his arrows at them. However, it’s worth noting that what he was doing was not actually placing feelings of love in his victims, it was more along the lines of opening them up in a way. It was essentially creating a situation where the two prospects were open to the idea of each other and through Cupid’s arrow, saw traits in the other they admired. Thus, creating a pathway to potential love. And I believe a similar thing is happening with Supernatural’s cupid lore. The cupids aren’t taking away freewill and making people fall in love, they’re creating situations and environments to where the prospects would be receptive to it.
Now, were John and Mary ever in love? I like to think that they were. The cupid created an environment to where they were receptive to it and ultimately, it was their decision to let those feelings the cupid helped open to grow to the point where it lead to Sam and Dean’s birth. Was their relationship perfect? No. It’s implied they had their fights and disagreements but that’s normal for any couple. Just because they had fights isn’t indicative that their love was manufactured. We do know for a fact that Jimmy and Amelia were soul mates and while it isn’t clear if they were matched by cupid, they certainly had their disagreements as well. Were John and Mary going to fall in love without the cupid’s assistance? That’s hard to say. And that question may never be answered. But I also certainly don’t believe that just because you’re touched by cupid, that you’re soulmates with your partner. If that were the case, a whole lot more people would be sharing a heaven. I definitely don’t believe Mary and John were soul mates. But it doesn’t mean that it was impossible for them to love.
Basically, I don’t subscribe to this idea that the cupids in Supernatural take away freewill. I don’t believe that the feelings John and Mary had were manufactured by heaven. Heaven created an environment and situation to prod those feelings along but ultimately it was still John and Mary who had the freewill in their relationship. They still called the shots. And at the end of the day, isn’t that what Supernatural’s really about. Freewill. That freewill is something that isn’t so easily taken away.
Anyways, hope you all enjoyed this. Keep in mind these are just my thoughts and opinions. They in no way reflect any of yours.
ANON THIS IS SO SWEET!!!! who are you,, you're so kind waaa 🥺💕💕 she's so pretty because she's meeeee 😇 /j
just for u... I'm gonna share an exclusive Smidge doodle from when I was warming up :D
For your actual question!! I've mostly answered this for both Smidge (here) and Cupid (here) !! I talked about the first canon scenes they'd show up in! But I can give you the first scenes they have that happen because of them :3
Smidge: Smidge would pop up in between Winter Soldier and Civil War! (I guess this would be some kind of post-credits scene? Maybe some kind of comic, like the Civil War Prelude comic? Let's not worry about that too much). In my world of color, Smidge's first scene would be her running around the woods and having fun. She's a little lonely, but she's free at least... and then she comes across Bucky! Bucky isn't very talkative, but he doesn't seem afraid of Smidge, which is a win for her! So they hang out for a little. She feeds him, she talks his ear off, and they have fun! They probably skip stones together or something. It's very, like, peaceful. Bucky finds her weirdly comfortable to be around, and Smidge feels the same; she's happy to hang out with someone again.
The scene ends when Bucky leaves. But before he does, Smidge asks him to come back again sometime, she hasn't had a friend to talk to in a looong time, and he's really nice! :D
unsurprisingly, he does. and he does that for like a year :3
Cupid: hmm, I imagine her in the background of a lot of scenes and having little parts at the start of the show. So I thiiink the first IMPORTANT scene she'd have would be when her whole side plot starts! Her whole bit is that Alastor asks her to keep Vox busy for him; he doesn't need Vox trying to interfere with his Dubious Plans at the hotel. (plus he needs to show Vox how having a spy is DONE because what do u mean he sent PENTIOUS??? is he stupid) Cupid when she is a pawn in the psychosexual drama between a radio and a tv, dude fuck my chud life
So the way this looks in my mind is: Alastor pulls Cupid aside or visits her in the kitchen or something. And he's like, "Cupid, my dear! You remember what you said to me when we made our little deal all those years ago, don't you? I seem to have finally found a use for your talents after all." and then it immediately cuts to Cupid walking around town, complaining to herself with her ears pinned back.
"oh that guys fucking crazy! [doing a shitty Alastor impression] Oh, Cupid, go keep the media overlord busy and out of the hotel's hair! No, I won't tell you how to find him, do it yourself! You're a capable woman! What is that guy talking about? How am I supposed to find Vox?" and then she walks into a shitty cafe or something. And he's right in front of her. And her jaw falls off.
This scene is so clear in my mind. I've been wanting to make a comic for it, but I've been busy :p But yeah! That's Cupid's first Important/plot-relevant scene!
THANK U SO MUCH FOR THE SWEET ASKS, ANON!! YOU ARE SO LOVELY, AND I HOPE YOU HAVE A WONDERFUL NIGHT!!! 💕💕💕💕
Hiii!! Matthew and I wanted to hear some yaps about your self insert!! <3 can you please answer questions 2, 5, and 8 from the recent ask game you reblogged? We look forward to your response!! 🖤
Hii :D!! Thanks for the ask, I hope u and Matthew are having a wonderful night!!! 💕💕
I did 2 and 5 for Smidge, so I'll answer these for Cupid!
2. when in canon does your self insert come in? do you have a scene in mind for your entrance?
In my mind, Cupid's been around since the pilot! (This is where I pull out the fake screenshot with her and go, "Look, she's been here the whole time!" But I haven't made it.. yet). I imagine her bit in the pilot is really short! Alastor summons her, like Husk and Niffty, and she's a little caught off guard because?? She's not the most useful?? What does he need her for? He says something to her about how he thought her skills would be useful at the hotel, probably makes a joke about how "her food's so good you won't even notice you're eating people meat!" And she's like :( "Aw, hey, come on, I WOULDN'T force these guys into cannibalism! Plus, you know that stuff is too expensive to buy in bulk for a hotel anyway!" and they laugh together. WHAT A BUNCH OF FREAKS!! They were friends at one point </3
So in the proper show, she's already there! I need to rewatch with Cupid-Vision to see exactly where I'd put her in it - but I think she'd probably first show up during Alastor's commercial ("our somewhat functional staff! :D" Cupid sitting at the bar squinting at a recipe book or smthn) I've also considered that it'd be fun if while Vaggie was trying to make the commercial she'd try to be helpful and give Vaggie some advice/tips. But because Cupid's an obnoxious cinephile, none of it is really useful. It's a commercial, girl, you're not making the next Citizen Kane
5. does your self insert have any special powers or abilities?
I answered this one here! :D
8. what is your self insert’s orientation?
All my self-inserts are bi like meee! :3 Cupid wasn't able to be open about her sexuality while alive, so in hell, she's much more vocal about it now !

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Your S/I is so pretty! I have to ask if she's friends/associated with Rosie cause they're both cannibals teehee
Aaa thank you May!!! 💕💕
And yes, she’s friends/associated with Rosie! :D currently still working out the details of their relationship, but atm my best friend Gel (@obsessed-pest ! they’re the sweetest ever and help me bounce ideas around) and I are thinking that Rosie takes an interest in Cupid, because despite being a cannibal she doesn’t live in cannibal town and is generally a bit hesitant to go there/interact with most other cannibals (her kidnapper/abusive ex was a cannibal, so she tries to limit her time around other cannibals bc she’s afraid of encountering him again). Rosie notices this and the general way she carries herself and takes an interest in her, she’s curious! Thinks she can figure out what Cupids deal is and help her out maybe. Rosie invites her to chat and have tea, and thru that they end up becoming friends :]
Cupids relationship with Rosie is how she ends up meeting Alastor too. Alastor owns her soul/her connection with Alastor is how she meets Vox so!! Her connection with Rosie is very important plot-wise, even tho I’m still figuring out all the details :p