Okay, I originally started making this over 2 weeks ago, but I got sidetracked and never finished it, but I went back yesterday to draw more of it
Basically I just wanted to draw Dark Choco and his past relationships with other characters
First off I drew him with Caramel Arrow Cookie, with him mentoring her in how to use a bow. I’ve kind of already covered how I see their relationship in an older artwork, but basically I see them having a pseudo older brother/younger sister relationship, while Dark Choco also acted as sort of a mentor to her
Next we have Dark Choco and Royal Berry, whom I also see them having a sibling sort of relationship (basically Dark Choco went out and just collected siblings like Pokémon, intentionally or not). While Dark Choco is older, here they’re both at least teenagers, Royal Berry’s just short. Initially they met simply because their parents were friends (I imagine Hollyberry and Dark Cacao probably kept the most in touch out of the Ancients post-Dark Flour War, but that’s just going off what I can gather so far), with Royal Berry befriending the shy Dark Choco Cookie, and later on they remained close friends, despite Royal Berry not being very enthusiastic about fighting or going on dangerous adventures (though that didn’t stop Dark Choco from occasionally roping him into shenanigans). Dark Choco just liked his friend, and he also provided a different perspective, considering everyone he knows in the Dark Cacao Kingdom is a warrior just like him. Dark Choco also acted as a bit of a wingman for Royal Berry when it came to Jungleberry, a young knight in the Hollyberry Kingdom, helping hype Royal Berry up and give him the confidence to ask her out, to which she agreed. Unfortunately Dark Choco just stopped coming over, after an incident in the Dark Cacao Kingdom that Royal Berry never got the details of as his mother never really told him, so he’s not sure what happened to his old friend. As for Dark Choco he wonders how Royal Berry is doing now (he’s unaware that he and Jungleberry got married and they had kids, he was only there for the first and maybe second date)
Then last night I drew Dark Choco and Second Watcher, which I finished earlier today. For the sake of simplicity I’m gonna call Second Watcher here Toffee Cookie, though I’m not sure if that’s my final name for him? (Also side note I just learned today that toffee is essentially caramel (well not really but it’s similar). For some reason I always thought it tasted more like coffee or honey, and thus a flavor I didn’t like. But I do like caramel, so I might actually try it sometime)
So initially I didn’t think much of Second Watcher, other than the fact that I’ve seen his name pop up quite a bit on here, which was a bit odd for a minor NPC. But upon looking again at that loading screen with Dark Cacao Cookie and a freshly baked Dark Choco Cookie, I noticed that the random Cookie holding Dark Choco Cookie was first off a man given the stubble, but also looked uncannily similar to Second Watcher Cookie, to the point where they might be the same person, and the Wiki at least seems to think so too (I’m aware the Wiki isn’t official or anything, but it is an interesting thing to point out). And that intrigued me, because he doesn’t look like a soldier or anything, he looks more like a nursemaid. Now how on earth did he go from a nursemaid to the second in command of the Watchers, the guard of the kingdom? There’s clearly a story there, so I came up with one of my own
So Toffee Cookie here was initially indeed a nursemaid for the prince (which good for him for breaking gender roles), and was basically his primary caretaker in stead of Dark Cacao Cookie (I don’t think Dark Cacao was a neglectful or absent father, it’s just that he’s a king with important duties and he can’t spend all his time looking after his son, and in seeming lack of another parent, he needs someone else to take care of Dark Choco). Dark Choco Cookie saw Toffee Cookie as sort of a secondary parental figure, sort of like Lancer and Rouxls Kaard from Deltarune? Only Toffee sees Dark Choco like a son as well, even if he knows he isn’t
Anyways, so one particular night, when Dark Cacao Cookie was absent from the Citadel as he was dealing with matters in distant reaches of the kingdom, there was an assassination attempt on the prince. They created a ruckus with the Wall, causing the guards to focus their attention on whatever was attacking them outside, diverting and distracting them so that they could get to their target. Toffee Cookie went to Dark Choco’s room to make sure he was unharmed or he wasn’t scared by all this (keep in mind Dark Choco’s not very old here, he’s like 4-5 in Cookie terms), only to find assassins trying to attack him. Thankfully, Toffee had combat training, as is required of any Dark Cacaoian, and on instinct he pulled out a concealed dagger and attacked the assassin closest to Dark Choco, picking him up and fleeing the room. The assassins eventually cornered them and so Toffee stood his ground and fended off their attackers with his dagger until help might arrive. This is how Toffee Cookie lost his eye, as is evident in the picture. Eventually the soldiers realized the deception and after taking care of the threat to their Wall, went on a desperate search to find the prince, hoping they weren’t too late. They eventually found Toffee Cookie, stained with his own jam and the jam of the assassins, surrounded by dead or unconscious assassins, fighting off the ones still remaining. They were able to get rid of the final assassins, and the attack was finally over. They found the prince unscathed, though clearly terrified from everything, and he was clinging on to Toffee Cookie for dear life, refusing to leave his side, even after Toffee Cookie collapsed from exhaustion and his wounds, staying by his side as the healers worked on him and into the next morning. Dark Cacao quickly came back after hearing of the incident and was relieved to find his son unharmed. Toffee Cookie was praised for his tenacity and even offered a spot on the Watchers, but he declined due to his current loyalty being to the safety of the prince, even if he wanted to join them. This made Dark Choco determined to work twice as hard at his training, so that he’d be able to take care of himself and Toffee Cookie would be able to join the Watchers like he wanted, and some years later, when Dark Choco was older, Toffee Cookie joined the Watchers, and eventually became Second Watcher Cookie. Not sure if he was originally First Watcher but stepped down when Caramel Arrow Cookie got promoted or if he only got as far as Second Watcher
Also side note I like the idea of Second Watcher being Caramel Arrow’s father, whether biological or not, so there’s more fuel for Dark Choco and Caramel Arrow being siblings
Originally I was gonna draw the two after the incident, with Dark Choco promising to train even harder so that Toffee can join the Watchers, but that would have required dialogue, and also I wanted to draw this scene more
There were gonna be more, but I either don’t remember who they were gonna be with, or it just didn’t fit with the stuff I was drawing, mainly relationships from post Strawberry Jam Sword
For example, I was gonna draw him meeting Purple Yam Cookie during that tournament, only for me to stumble across my old post talking about Dark Choco’s connection to both Milk Cookie and Purple Yam Cookie, and I realized that based on what Purple Yam Cookie says (the fact that “the Dark Choco Cookie he met didn’t know how to smile”, despite the fact that Young Prince Dark Choco Cookie’s sprites almost all show him smiling, other than anger or defeat/exhaustion sprites, implying that he used to smile a lot, and that he “didn’t wear flimsy clean armor”, despite us knowing Dark Choco wore that armor even during his attack on Dark Cacao Cookie), Purple Yam Cookie must have only met Dark Choco Cookie after the Strawberry Jam Sword.
Edit: So I’ve been told that Purple Yam actually probably met Dark Choco before the Strawberry Jam Sword, for the reasons listed here (I’m trying to link it), so what I say here might be moot. Ah well, I still didn’t draw more than an unfinished sketch
But anyways yeah I ended up cropping the canvas short because I couldn’t think of any more and I just wanted to finish this piece
Writing this I think some other ones I was going to draw were Jungleberry (mutual respect as fighters) and his first encounter with Milk, but oh well
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