I actually don't think Jessies interractions with Cloud are what made her popular. Or more specifically, although she became popular through her interractions with Cloud, Cloud himself had little to do with it, it's just that Jessie was fun to interact with, and since we are Cloud, those interactions HAPPENED to be with Cloud.
I think she, as an individual, is more interesting than her relationship with Cloud is.
I think the enjoyability of her character would be served better by seeing her interact with a host of different characters, and seeing how her personality handles that, than by watching her specifically with Cloud.
With Tifa for instance, I think that specifically her bond with Cloud makes both characters a joy to watch. I think Jessie was simply a joy to watch by herself, I think Cloud mainly held back that personality. In my mind, watching her, for instance, interact with Zack sounds way more interesting.
How is this for remake speculation? Jessie DOES survive, meets up with alternate universe Zack, and they travel after the party in the ultimate buddy cop movie!
That's your opinion, but I think her dynamic with Cloud
is part of her popularity. And there are things between them still unresolved - the possible pizza date, for one (which could be incorporated into a Gold Saucer date of her own with him - she
was the Princess of the play, after all). Their growing friendship, for another - by the end of Chapter 4, he's warmed up to her and they've formed a connection. It would be nice to see more interactions between them with that in mind and see how different they'd be compared to what came before. Because I think his responses and reactions to her attention might be a bit different, maybe even a little warmer, with their friendship now established, especially since he'd be glad to see her again after thinking he'd lost her in the pillar.
Nah, he doesn't really treat them badly, but yeah, he's awkward and has said/done dumb things that can be off-putting. Aside from running around doing random favors that people usually pay him for anyway, I'm not sure what he has done that would earn him the affection of multiple women?
Maybe the best thing he's done for any of them so far is insisting on saving Aerith. Or trying to listen to Tifa? As for Jessie, I just don't get it. He's outright rejected her multiple times. Probably why I would prefer it if she didn't have any further involvement in this mess.
He didn't necessarily reject her - remember, Nojima said that his harshness is nothing more than a front. Which means that he doesn't mean
any of the harsh things he says. He's just trying to get attention and look cool. But Jessie sees right past that, which is why she keeps ribbing him - because she knows she can. She's the one who begins to get him out of his shell a bit, and by the end of Chapter 4, they've begun to form a friendship. He shows genuine concern and warmth for her, asking if she's hurting, carrying her into the bar, encouraging her when she laments having to stay behind. Also, their dialogue during the bike chase was more playful banter, even on his end, than serious discussion - he actually laughs a little when she says "My hero!" about a minute into the chase.
And when she asks him if he's going to take her breath away with his skills, his response - "Don't blame me if ya get sick." - is not a denial. He was definitely trying to impress her. He didn't have to do the wheelie when they got topside, but he did it anyway, again likely to impress her since he surely knew she'd like it. And he never once told her to stop snuggling on him. Also, when she hugs him outside her door, his attempt to get her off him was half-hearted at best - he's strong enough that he could've easily gotten her off if he'd really wanted to. And when she first hugs him, he lifts his arms to start hugging her back before catching himself and just leaving them out there and slipping back into his shell.
The very fact that, if "no promises" was chosen, he was even willing to consider accepting her date invitation shows that he could've had at least a little interest in her. Also, if "no promises" was chosen and Cloud talks to her twice before leaving for Reactor 5, she reminds him about their dinner date, telling him to hurry back so her home-cooked pizza doesn't get cold. The fact that Cloud doesn't tell her he hasn't made up his mind yet or that he isn't going (which, as blunt as he can be, he'd have no problem doing) could mean that he decided to accept her invitation.
Also, in Japanese, Cloud is much more tender to her. "Are you seriously that desperate?" was, in the Japanese version, "Is this how it's gonna be?" and "My hero... so gentle." "Just try to hold on." was, in the Japanese version "You saved me again." "I'll save you as many times as you need." Which has a much more potentially romantic undertone to it. Jessie is also the first of the girls that Cloud gives full and complete eye contact to, even initiates it at times. His eyes follow her a lot.
So overall, he may not be quite as uninterested in her as some people think. It's just more subtle than it is with the other girls, so it can be easy to miss. And since he's inexperienced and trying to put up a harsh, cold front to look cool, it can seem like he doesn't care when really it's possible that he does. He just doesn't know how to react or respond to her attention.
I can kinda see Yuffie doing that. Maybe.
