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Okay so, we all know that of the main destiny Island trio, Riku is the one we know the least amount about as far as his family goes. Kairi had her grandmother and then later implied to live with the mayor. Sora's dad was mentioned to bring Sora and Riku to the island as children -quick aside, that is extremely fucked up for him to row a 4 and 5 year old to a deserted island and leave them there and come back for them later, that's extremely irresponsible and borderline suspicious but whatever- and Sora's mom is heard in KH1. But no one, not even Riku himself has acknowledged any family he might have. All we have is what Riku said in KH1, "We may never see our parents again." Which isn't a hard confirmation, just a vague implication that he has some sort of parental figure around. And not to point at the lack of evidence to be evidence itself, but it does feel kinda intentional and maybe important going forward so I'm gonna throw my hat into the ring before something canon is finally revealed.

What I think, is that Riku's family situation is not great. With how desperate he was to leave Destiny Islands, and we see he was willing to pay any price to do so, makes me think that leaving his parents behind wouldn't have been something holding him back to say the least. If you don't have something good to leave behind, it makes it easier to leave. We know Kairi didn't want to leave, she was happy with what she had on the islands, but didn't want to lose Sora and Riku so she went along with it. Sora does seem very eager to leave the islands, but we see throughout the rest of the games, going back was always the end goal. Riku, his desire to go back to the islands always boiled down to it being because that's where Sora wanted them to go.

Now, the actual head canon. For starters, I like to think Riku's father walked out when Riku was still very young. Be it for any number of reasons, feeling tied down, the call of something greater, not ready to be a father and just going scorched earth with it all. The reason why doesn't matter, because the end result leaves an emotionally distraught Riku and a resentful mother -which I'll get into in a moment-.

See this can fit nicely into Riku's future canon motivations and some popular fan theories. Say we believe that Riku himself is a part of some great family line of keyblade wielders. Maybe somewhere on Ephemer's family tree, there is a branch that leads all the way down to Riku thanks to his father. If said father walked out years ago, that traceable tie would be lost leading to no one knowing anything about said family lineage.

As far as canon goes, it's obvious that Riku has a fear of abandonment. That's one of his driving factors in KH1. He thinks Sora and Kairi might leave him behind, so he leaves first. He convinces himself so easily that Sora is abandoning him and Kairi, it didn't take much for Maleficent to lead him down that conclusion. And if he already faced being left behind by his father, at a young age, that could be why he harbors that fear later in life, so much so that it leads him to make desperate and rash decisions.

And to go even further, could even strengthen the connection between Riku and Mickey. To have a friend, border line father figure always trying to help Riku, protect him, be by his side to help him get through anything, when he went so long not believing that he could rely on anyone else would be very freeing for him. Mickey isn't the step-dad, he's the dad that stepped up.

As for Riku's mom, I think she's resentful and neglectful. If when Riku's dad walked out, regardless of why he actually left, she turned her grief on her son. If she thought he left because of the child they had, it could fester into blatant resentment of said child. If the both of them feed into the idea that it was Riku's fault, it's just an endless cycle of pushing that abandonment and fear into Riku.

So, she blames her son but can't just abandon him on his own, so she continues to raise him but as an obligation. To do the bare minimum and keep him at arms length, not subtle in her resentment towards him. I don't think she was directly abusive, but she certainly didn't aim to be present for him when he needed it. The "I feed you, clothe you, and keep a roof over your head, what do you have to complain about." The sort of parent that made it clear once you were 18 you were out on your own. Riku learned young he needed to take care of himself, he couldn't go to his mom so he internalized the idea that he couldn't go to anyone for help.

This also leads into Riku's need to be needed. He had to be the strongest, the fastest, the smartest, because if he wasn't, what sort of value did he have. If he couldn't do it all, wouldn't everyone else just leave him too? If he could prove himself worth it, maybe he could get his mom to want him. If he was strong enough to keep Sora and Kairi safe, they'd never need to leave him. So, in KH1, when Sora is proving he can take care of himself, that he doesn't need Riku to protect him, Riku is just spiraling in the idea that Sora will leave him, replace him. I think that's why Riku was so desperate to save Kairi no matter the price, no matter what he had to do, because if he couldn't do it before Sora could, he'd be just as worthless as he feared he was.

This could also lead to an interesting dynamic between Riku and Maleficent. I've always been obsessed with the scene where Maleficent says she views Riku as a son. I do believe she was just saying that to further win Riku over, but if we take this headcanon into account, it actually paints it in a much more manipulative light than it already was in. If she could pick up how badly Riku wished he had his mother's love, it's a no brainer to give him the idea of a motherly figure caring for him. Give him a taste so he'll cling desperately for more and be all the more easy to follow wherever you point him towards. I like this idea a lot because it's so tragically sad, but at the end of the day, in canon, Riku and Maleficent's relationship with each other ends the second Riku is possessed by Ansem. In KH2 when the two of them are in the same room, neither even acknowledges the other and it's kinda a shame, I would have liked to see something like what Riku and Ansem had at the end of KH3.