They would have to live up to the expectations of the grieving adults around them and have to compare against their peers. Even, tho they cope in very different ways, they understand each other on a level, even if they don't agree all the time. They just have that bond.

The fact that it was likely he was on the streets during the dark flour war and it's likely the reason for he doesn't have a home or a family just adds so much to him. It would add so much to his relationship with hollyberry and why he is the way he is. Based on the time and what was happening, I can see him having a time where he was resentful of the culture of the hollyberry kingdom, especially the nobles, because of how they will won't bat an eye for those who were really effected during the dark flour war.

To add on it is implied that he was more likely to resort to fighting, which is were I can see some still being he only solves problems through brute force. And to be fair, due to his situation it's not like he had the luxury of many other options of solutions, plus it possibly being a trauma response. I think their is lots to explore around that time of his life and the trauma around it.

Also the implication that hollyberry disappeared when he was child or young teen, you can imagine the hurt of him building up trust in holly only for her to just disappear in his most vulnerable, yet informative years. For more personal takes after the whole fiasco and him being taken in.

Overall, I think wildberry cookie is very neat and just thinking of what he went through really makes me a bit sad, especially with my headcanon that he was actually sick for good chunk of time, which is connected to I'm not liking berry juice due to him having a complete intolerance to the point of a reaction and maybe even an server allergy to the yeast in it.

So, think of all the rumors, nasty comments, and general many trying to leech off of him while he is young to get the status and power he will have once he gets older for there own gain prince or not. And the press, oh it would be a pain, positive or not, because they would likely spin his story as if it was some fairytale, even though he likely still has trauma he's trying to and kind of forced into a role model role for peers his age.

Like, it rots my brain. Average citizens giving him gifts and cute letters: rubs my brain in the right way.

high standing noble house members giving up their part of grandma's will: ferally chewing it.

Royals of other kingdoms coming with there finest to try to impress the fam and him: Diving in head first.

Him and royal berry would have that mom got empty nest syndrome vibe and it kind of made it difficult for them to bond at first, but they slowly grew close. I think even before Hollyberry's departure, he has a bit of a caretaker, especially with all of wildberry time on the street as well as the things he probably shouldn't have been exposed to due to the dark flour war. Afterwards, they definitely went through a rough patch with grief from hollyberry being presumed dead and someone basically delivering her shield back to them. One top of everything, he has on his plate, he also have an baby brother that got every emotional wound ripped back open and reliving his trauma most likely made him regress a bit left in his care.

Royal berry had to pick up were hollyberry left off and raised him through his informative years, the good, bad, tears, and fears. So, they definitely more vulnerable with each other and royal berry cookie would be one of the few cookies he feels comfortable letting his walls down around. In summary, wildberry is a eldest child that had to parent their younger siblings as well as jungle berry being honorary mom and they both qualify for a court settle. Also you can't tell him and the the rest not including those after him (to an extent) have that empty nest baby sibling brand of protectiveness over him and definitely doesn't have their suitors go through a whole venting process, plus a whole gauntlet and middle fair style trails to have his hand.

Wildberry and princess cookie, prime example of older sibling with an ambitious goal and younger sibling that things they are cool and sometimes get in trouble due to getting into danger to do things like them. He was most likely the root of Princess's spirit, when it comes to adventure to a t. She likely seen him go off to training or even watch him train and it was at least the start to her love for adventure and fighting. I can see him gushing about all his favorite things about training to princess cookie when he comes home from training, especially during that preteen phase of not really feeling he can't do so with adults due to the fear of not being taken seriously as well as many some stories about hollyberry, she used to tell him herself.