Got an error message when I tried to post this and I'd have been SO distraught to lose two posts in a row, but fortunately I saved it this time... Here we go. Let's try a post instead of an ask this time.
Hi Jen, I know you've deactivated your account since sending this but ^^; I'll answer it anyway for other people. Sorry for the long delay, I was on Tumblr / FOP hiatus last year.
I see Chloe as being completely blinded to the dark hearts the Anti-Fairies are said to have in canon; she usually sees the world in gray tones unless very specific conditions for annoyance and betrayal fall into place. She has a lot of tolerance for Anti-Fairies, probably because Foop doesn't really get her angry and he just kind of makes things mildly inconvenient. Some examples of angry Chloe that come to mind are:
-> Perhaps most obviously, Kevin's betrayal. Chloe gets right in his face, jabbing a finger at his chest, spitting that he's a "Despicable little piece of Crocker," which is already funny enough, but I think it's extra hilarious since in "Fairy Con," she prevents herself from swearing by saying "Crocker" instead. Probably not intentional on the writers' part but I still think it's funny. I like how as far as we know in canon, Kevin's reaction is to wordlessly turn away from her and leave through the window, these two are so… chaotic.
-- Chloe seems more guarded around Kevin in the episodes after he betrays her even though he did everything necessary to fix the original conflict… mainly because Kevin stood between her and the Hall Monitor position she wanted. When Crocker says that Kevin will be named the new Hall Monitor, Chloe first acts shocked that Kevin even deserves the title, then screams "THIS IS SO UNFAIR!" while she's still standing in the classroom in front of everyone and I think we should acknowledge that.
-> Another angry moment: Chloe straight-up cursing Timmy to lose the ability to speak because he made her late for school in "Tardy Sauce"- something she did deliberately to prevent him from using magic, which is kind of uncool considering he could have easily ended up in danger and been unable to wish his way out of it ngl. Also I did check and she literally refers to him as "the most selfish, horrible former friend in the known and unknown universe, including black holes." Like, girl holds no punches when she's tipped from seeing you as morally gray to morally black. The literal next thing she does after this is run into class and throw Timmy under the bus, shouting "It was all Timmy's fault!"
-- On a side note, I do find it telling that Timmy isn't really one for denying people a wish. I'm pretty sure with Chloe he gets a little annoyed, but generally points out her wish flaws so she can learn from them- even when other kids like Mikey and Tootie ended up with temporary wish abilities, I'm pretty sure he didn't constrain them, but just tried to advise them and let them learn. Didn't even interfere with Norm and Chester in the early stages when things were chill. Just a side note on their characterizations that I think is interesting because I think it says a lot about Chloe's paranoia and how she wants things to be exactly the way she planned them while Timmy is more adaptable.
-> Chloe loses her temper in "Dimmsdale Daze" to the point that she shouts at kids that they're "monster children with evil in their hearts" even though all they did at the time was ask for popcorn.
-> Even early in the series, Chloe is highly passive-aggressive (and then directly aggressive) towards Timmy on his birthday, so driven to insanity that she refused to go to sleep so she could be "better" than him. This happens at the start of the episode rather than after a long day of chaos and stress like "Daze," she is not and has never been okay.
-> I do seem to remember her having a lot of animosity towards Timmy's parents as well, and she definitely has gripes with Catman and is uneasy around Dark Laser, but I think we've covered all the obvious Chloe conflicts I wanted to hit (besides her parents, but that's not for this post, I think).
SO as for the question about Anti-Fairy relationships: Chloe obviously cares a lot for Foop. Although there are multiple times Foop tries to hurt or sabotage her in some way, she forgives him. I think she simply doesn't take him seriously because he's, like, 7 to 9 years old. I basically interpret Chloe as a character who tries not to make assumptions, but when someone strikes a nerve then she'll make assumptions anyway and react explosively until she cools down again.
Foop keeps trying but does not strike her nerves the way that Kevin and Timmy do. There is a difference between "Betrayed by someone I genuinely consider a friend" and "New girl showed up in class and started bullying me but I don't know anything about her so I am confused but not betrayed."
I also like to imagine Chloe would fall for the "classy bad-boy villain" vibes that Anti-Cosmo projects because it's funny to me. In my one-shot "This Is a Box," Chloe meets Anti-Cosmo for the first time and describes him as "the extremely good-looking British Anti-Fairy." When she's introduced to him properly, she greets him as, "Oh, you're Foop's dad." This irritates Anti-Cosmo considerably because he does not like playing second fiddle to his son, and she calls him "Mr. Foop's Dad" again later because that's just how she sees him. She met Foop first, Anti-Cosmo is Foop's Dad.
I think Chloe and Anti-Wanda might get along, but Anti-Wanda is minorly mischievous and relatively harmless, so the vibe would probably be Chloe asking how Foop is doing while Foop is standing there holding his mom's hand and being embarrassed. I also feel that Chloe is the type who would leap in to join the Anti-Fairies on the field during the Fairy World Games if she felt like they were the underdogs. It's what she does.
I do feel like Chloe would continually brush off the Anti-Fairies' "evil" side as drama and exaggeration because she wants to see the good in everyone, and I do feel like it would be hard for her to see anything truly evil about Foop because he's a little kid.
I was going to add something in here about how Chloe would appreciate the Anti-Fairies as people but wouldn't be lured into doing evil alongside them, but then I remembered a crucial piece of Chloe canon:
-> She totally broke into Timmy's house and stole a collector's item from his dad. That is actually a thing she did and the official canon is that this theft launched her into a life of crime as she joined a gang, stole from other kids, and started fooling around with deadly lasers. Cosmo, Wanda, and Timmy scared her straight and pulled her back, but when I think about it then yeah, Chloe absolutely would get swayed by the Anti-Fairies to do crimes.
tl;dr - I'll take any opportunity to discuss Chloe's darker side, she has so much coldness in her heart and we should always remember that without the support of Timmy and her godparents, canonically she'd have spiraled into a life of crime. Also she would definitely hang out with the Anti-Fairies, especially Foop because he is her baby.
