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1. Similar patterns of flirting

Unlike Rise, Yosuke is of course a lot less intentional and a lot more oblivious to what he's actually doing, but his behaviour is actually very similar to Rise's in some ways.

For example, the both of them find an in with Yu through "being shown around" Inaba.

(actually there's a scene with naoto's first day at the school, where a few girls are trying to flirt with naoto using the same lines of showing him around, so that's fun.)

There's a difference in context here - Yosuke is playing that senpai-adjacent role for Yu, whereas Rise is asking Yu to play it for her (even though Inaba is Rise's hometown, and when you take her to souzai daigaku she says she's always wanted to go there).

But this difference is also important because...

Yosuke's type is someone he can look after. (Btw, this is an extremely common male response in Asia - that men like dating someone they can look after. Remember this because it'll come up again later.)

I think throughout the course of the game Yosuke is very much consistently someone that likes taking care of people - quite obviously he looks after Teddie, but he's also always looking out for Kanji and everyone else, actually.

But there's something that changes slightly between him and Yu - as their relationship develops, Yosuke becomes more willing to be the one being looked after, but by Yu especially! This is something that is picked up on by others in the group, such as when Kanji says that Yu tends to spoil Yosuke, or when Chie tells Yu that Yosuke is going to come begging him soon.

Neither Kanji nor Chie talk about how Yosuke asked them for help - because Yosuke, for the most part, is pretty resistant towards asking people for help... unless it's Yu. Yu is the exception in this regard, because where most people see Yosuke as being reliable, they also know that if Yosuke has issues, it's Yu that he turns to. And he does! In front of Yu, Yosuke lets himself be vulnerable, both in more serious settings but also in casual ones. Look at how Yosuke playfully ask Yu to "save him/them" (from Yukiko, Rise and Chie's cooking). It's a little dramatic. It's a little whiny. And it's all part of that role!

But this is exactly the kind of role that Rise is playing as well.

In Japanese culture, there is the concept of 甘え (amae), which is closely related to the (perhaps more commonly known) Chinese notion of 撒娇 (sājiāo). It's hard to explain this in English because it's not really a concept that exists in Western contexts in the same way, but I think it's important because Persona is ultimately a Japanese game, and so the cultural norms and contexts that inform the relationships there are important. It's been talked about in more detail by people smarter than me (see: Takeo Doi, 1971) but the tldr is that it refers to a kind of childishness employed as a means to seek indulgence from a loved one - it's a little bit affirmation, it's a little bit flirtation, but really, the point is looking for someone to care for them. And it works the same way for the other person as well - to indulge is to love! (Remember Yosuke's response of wanting someone he can look after? Yeah.)

When Rise drawls out the word "senpai" and whines a little, that's one example of her playing up that role so Yu would pamper her (actually I don't play in dub, so I'm not sure if she does this in EN too). But we see this with Ai as well, when Ai tells Yu to carry her shopping or buy her coffee. Ai is of course perfectly capable of doing both things, but the point is to have someone like you so much they do things for you.

Compare this to the way the others ask Yu for help - there's hesitation, and it's framed in a "if you have time, could you..." sort of manner and is markedly less playful. I think to some extent it's also their personalities, but that's kind of the point here.

I think it's important to caveat at this point that this "submissive" role during amae isn't, like, a fixed role that they assign themselves into in their relationship - critically, it's temporal, contextual and momentary. Yosuke and Rise are only playing up their childishness so they can get attention from Yu in that moment, but it in no way speaks to how they expect their relationship to function, because it's just brief instances of flirtation. For both Rise and Yosuke, their relationship with Yu is still primarily defined by their equalness and what they can do for Yu as well. It also goes both ways - Yu is also welcome to do the same with Rise and Yosuke! It's also very much a purposeful demonstration of vulnerability, because if you've read the signs wrongly, then it may not be perceived as flirting, just general annoyingness. Which is why...

I think they're both particularly sensitive about accidentally being a bother to Yu, and the way the both of them speak has these layers of boldness and shyness interspersed and folded into each other.

To put it another way, you can think of this indulgence as an extension of the love language of acts of service - and amae is essentially a way of pretending to be helpless to encourage that act of service. (this is an extremely dumbed down definition stripped of nuance)

The point here as Rise flirts with Yu in this manner... I think so does Yosuke, even if he's not totally conscious of it.

2. The shared fear of loneliness

Both Yosuke and Rise express this same fear - Yosuke's shadow reveals his fear of being alone so he actively surrounds himself with as many people as he can, while Rise reveals in her slink that she was a shy, lonely child and became an idol because she thought it would help her connect with people and make more friends. There's this powerful desire of acceptance on their part that forced them towards behaviour that they felt would make them desirable and liked - Yosuke makes jokes and buys food for his friends and tries to be a dependable big-brother type, and his shadow says he's only like that because he's terrified of being alone, while Rise's idol image is about being bright and enthusiastic and bubbly, but her vulnerable moments reveal her to be withdrawn and she says it was all an act.

I think there's a really interesting parallel here, because they both learn that it doesn't really work the way they hoped - the relationships that they had previously formed can be superficial (Yosuke talks about this point with Marie and Yu on the rooftop, while Rise learns that people only see Risette but not her), or temporary and easily forsaken (Yosuke doesn't really have anyone calling him back after his move, while Rise talks about how quickly people moved on from her).

Critically though, it's also in how they are resolved, and in both cases, Yu is the catalyst that helps them understand that not only is that desire normal and understandable, but that both that desire and their responses to it are all part of them. Yosuke's and Rise's cheerfulness and care are not any less meaningful just because of where that sentiment came from. There's no real Yosuke or real Rise, and while this is also a theme for the rest of the IT, I think it's with Yosuke and Rise especially that this particular thread of a fake self created to be accepted and help them make friends is especially pronounced.

(for Kanji, his violent, abrasive self was created to hide away and push people further away, while Naoto wasn't seeking acceptance amongst peers, but their individual ideal of whom they should be).

The distinction here is meaningful insofar as it then speaks to how Yosuke and Rise subsequently perceive Yu in relation to themselves and the rest of the team. For both of them, Yu was the first person where they actually felt Seen with, and in Rise's case, it's what sparked her attraction to him, with her starting to flirt aggressively with Yu after her rescue. I think that in Yosuke's case it's very much the same thing as well, which is how we have Yosuke calling Yu his 相棒 (aibou) shortly after the fight with Yosuke's shadow. I can't place exactly when Yosuke starts doing so, because it can be as early as Marie's slink rank 1 if you did it right after, but in their conversations after the fight at the liquor store, I think the foundation is already there.

In English, 相棒 is translated as partner, which I guess is a fair translation that is captured by the sentiment of "partners in crime". It's a term that is also used in, say, buddy cop pairs (like Reno and Rude in FF7. It's also how Adachi refers to himself, as Dojima's aibou), but it's intended to capture that essence of someone that you trust above and beyond everyone else. Working on a case and your boss and colleagues say no? Doesn't matter, you aibou's got your back. It's the person that you share this absolute connection with, that knows you like you know them, maybe even knows you more than you know yourself.

But imo there's a bit of nuance that is lost, because there's also the weight of exclusivity inherent in the term - you can have a lot of friends, but only one aibou. It's one of the highest, most intense and exclusive relationship that you can have with someone... platonically.

Kick that platonic label off and we find that Yosuke and Rise are the only two that end up attached to Yu with that same, absolute intent, and hold this similar wish for some exclusive relationship with Yu. By helping them understand their loneliness and what the intimacy of being seen means, Yu has triggered the same reaction in both Yosuke and Rise - just coloured slightly differently, romantic for Rise and platonic for Yosuke. But Yosuke's route wasn't even intended to be necessarily platonic so

3. They're the two that ask Yu about his type the most

I think that with a heteronormative lens, it's easy to interpret Rise's question as one coming from romantic interest and flirtations, while Yosuke's questions are coming from patterns of locker room talk, but fuck that, I think they're both testing the waters of romantic interest and looking to see what Yu would say.

Of course, if Yu takes that one opportunity he has to say Yosuke is his type, Yosuke gets flustered and his hair-trigger nohomo reaction kicks in... but then he goes into a thing where he talks about how yeah, he'd make a pretty good boyfriend! He likes Yu's answer here, he even has the little flower animation of happiness!

In contrast, if Yu picked Kanji, the conversation derails into a thing about Kanji's manliness. Furthermore, considering that Yosuke's romance route was cut but all of the previous conversations and interactions remained, there's no reason not to think that Yosuke wasn't responding positively to Yu's affirmations, even if he didn't necessarily understand what they meant at that time.

In the same way, if Yu responds positively or goes along with Rise's questions, Rise is also noticeably happy about it.