Supernatural: 10 Characters Chuck Should Have Been With (Other Than Becky)
Before he was revealed to be the main antagonist of the entire series, Chuck brought in some real moments of hilarity to Supernatural. One of these happened to be his involvement with Sam Winchester fangirl Becky Rosen, a relationship that was doomed to fail since Chuck was actually God.
With that in mind, though, Chuck would have made one half of an interesting couple with a bunch of other Supernatural characters. There are many scenarios that could have allowed for these romances to happen, so here are 10 characters with whom Chuck should have been with — if nothing else, than for sheer entertainment.
10 Jody Mills
Jody was feeling lonely in Season 8, which was when she went on an ill-fated date with Crowley, who tried to have her killed. This would have been the best time to add Chuck into the mix, with his intent to prey in on Jody’s loneliness.
It would’ve made for a compelling scenario to see the tough Jody be courted by the kooky Chuck, and for her to realize she’d been dating God all along. Along with being a big twist, it would’ve provided Jody with motivation to take Chuck down in Season 15 for fooling her.
9 Charlie Bradbury
Charlie is gay, sure, but this would’ve presented a great opportunity to show a female version of Chuck thrown in the mix. With his powers, putting on a female form would’ve taken a snap, and it would’ve been something else to see a female God here.
Charlie never had any relationship that lasted, so this could’ve been the one where she felt she had someone with a similar odd streak that she carried. Chuck’s flashy nature would’ve gone well with Charlie’s, and there’s no doubt it would’ve been memorable.
8 Crowley
It was heavily implied during the series that Crowley was bisexual, what with the many times he flirted with the heroes and even kept a picture of his kiss with Bobby. However, the real intrigue would’ve been to see how Crowley would’ve used this relationship to his advantage.
Being the character nobody could ever trust, the dynamic here was bound to be interesting, as the cool and suave Crowley could very well have played with Chuck’s emotions to maintain his dominant position in Hell.
7 Lilith
Although fans didn’t see it on-screen, Lilith was resurrected by Chuck in Season 15 to go after the Winchesters. Her resurrection brought a change in personality, as she became far more cheerful and sarcastic.
A relationship with Chuck would easily have taken fans aback, as demon Lilith evolving from her vicious personality to a more humane one sounds like a fun angle. Not to mention the possibility of seeing Chuck trying to manage a romance with his son Lucifer’s most trusted general.
6 Linda Tran
Over the years, Chuck has tried many ways to keep tabs on the Winchesters, and using the widowed Linda Tran sounds like a good plan. He could’ve come back around the time Kevin became a prophet, and been a father figure of sorts to Kevin, using his own status as a (false) prophet to bond with him.
Linda Tran was also a very feisty woman, meaning the combination of her with the otherwise talkative but weird Chuck would’ve brought about a highly unorthodox couple.
5 Rowena MacLeod
Rowena was very much attracted to Lucifer when she saw him for the first time, feeling as if his immense power made him an alpha male. She also had a good relationship with Chuck in Season 11, which was when the show could’ve given this relationship a go.
The storyline had potential: Rowena attempting to be better because of her relationship with God himself, only to slowly realize that this guy was hardly as nice as she thought. Plus, it would’ve been hilarious to see Lucifer and Crowley feel like step-siblings.
4 Dagon
Similar to Lilith, Dagon was another demon who had a sadistic yearn for power. Being Lucifer’s minion her whole life, the scenario here might have been where Chuck made the moves on her to act as his spy toward Lucifer.
Had they had the chance to meet, this also would’ve opened up the possibility to see a more suave Chuck, as Dagon seemed to be attracted to authoritative figures. Along with that, having Chuck in a relationship with a Prince of Hell — the same species that killed Mary Winchester — would have opened up storylines concerning Sam and Dean as well.
3 Doctor Hess
By his own account, Chuck mentioned the conflict with the Men of Letters to be “weak,” something the fanbase agrees due to the lackluster execution of the plot. At the center of this was Doctor Hess, the leader of the UK branch.
Having Chuck be directly involved with this angle sounds like a better plot, and it would’ve been doubly interesting to see him romance Doctor Hess. The notoriously cold Hess would most definitely have been far more intriguing if fans had seen a humane side of her. Chuck using this relationship as a way to carve out more of his “story” would’ve turned them into a deliciously unsettling couple.
2 Mary Winchester
Mary was notorious for always being in two minds, never knowing if she loved her sons and constantly flip-flopping between love interests from Arthur Ketch to Bobby Singer. To make a real plot out of this, Chuck could’ve been introduced as a love interest, and have it be hidden from Sam and Dean.
A secret romance with God himself sounds like a trap Mary would fall for, and it at least would have given her an interesting arc to go through. It could also have tied in with Mary finding her way to Heaven with Chuck opening up the path for her.
1 Bela Talbot
Just how Chuck is duplicitous, opportunistic, and a flirt when he wants something, Bela is cut from the same cloth. She possessed an erratic personality, becoming friendly at one point, only to betray the next.
There’s no doubt Chuck would’ve been very attracted to such a character, and both of them would’ve used this relationship to further their own goals. They could even have become a villainous couple, one who plots and schemes against others just for their own amusement. It certainly sounds like a match made in Heaven.
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