Well, at least Aerith is a walking corpse. Jessie, meanwhile, is just a corpse.
Let's not get too delusional here. Why would Jessie need to have a scene with Cloud in Chapter 14? She already had time with him at the earlier parts of the game, albeit with Biggs and Wedge. What makes her so special to warrant a scene with similar gravitas as Aerith, Tifa and Barret, who---I dunno--- are part of the main, MAIN OG cast? The ones who actually get to be in your party? The ones (plus Yuffie) you actually get to have a gondola date? It wouldn't make sense meta-wise.
Jessie is already fortunate for all the screentime she gets this remake, when she was just extra in the OG. Even if she could possibly be still alive and make a comback in the latter parts, she is just not in the same level of importance as Aerith, Tifa and Barret are, either to Cloud or to the story.
I don't like to sound harsh, but let's get real. Jessie is not a real option.
Not true. It's very possible for Cloud to have had some attraction to her. You have to pay attention to his body language, eye contact, and what he doesn't say as much as what he does say. You also can't take all his words at face value because, as Nojima said, his harshness is pretty much a front. Jessie keeps flirting because she knows he doesn't really mean those things that he says. And in Japanese, he's much more tender to her as well. For example:
English
Jessie: My hero... so gentle
Cloud: Just try to hold on.
Japanese
Jessie: You saved me again.
Cloud: I'll save you as many times as you need.
English
Cloud: Are you seriously that desperate?
Japanese
Cloud: Is this how it's gonna be?
If you watch his arms and hands when she hugs him before inviting him over, you'll see that
he starts reaching up to hug her back but catches himself before doing it and puts his facade back on. Also, at no time does he tell her to stop snuggling up to him on the bike. Which means that he didn't mind her doing it, he just didn't know how to respond to it. And, in one of the bike end scenes, he actually tells her to hold on tight, and when she clings to him, he never says anything about meaning the bike instead of him. Also, consider this bit of banter from the minigame:
Jessie: You gonna take my breath away with your amazing skills?
Cloud: Don't blame me if ya get sick.
Cloud's response
is not a denial. He never said no to her question. He
was trying to impress her. And he even bantered with her, basically asking if she was having fun. His seemingly harsh replies didn't daze her because she knew he didn't mean them - you can tell because she laughs about them, almost like he was joking in his own odd, Cloudesque sort of way. And when she kissed him, he was surprised and flustered and caught off guard, not uncomfortable. He just didn't know how to respond, so he didn't. He wasn't being mean to her, he was just overcome. Again, he never told her to get off him, which means he didn't mind her being there.
Whenever he and Jessie have scenes together, watch his eye contact. He follows her almost all the time, so much so that in Chapter 2 she has to move the materia she's holding to even get him to notice it because his gaze is so fixed on her. During their conversation there, he's again trying to impress her with his cool veneer and SOLDIER talk, as you can tell from the small smile he gives her during that time. She isn't fazed because she sees right through it. And it's her - not Tifa and not Aerith - that gets him to let down his hard edges first. And if she could do that in just one night, she could've done a lot more if they'd had more time together.
If you watch when he carries her into the 7th Heaven, you'll notice he gives her a little smile just before that. Watch how his mouth goes up slightly when he goes to pick her up. And he didn't have to do that at all. We know Barret could've done it because he carried Wedge later. But Cloud chose to do it, and not grudgingly, either, but
warmly. He knew by then that she liked him and knowingly did something for her that would feed that feeling. And not only that, he
immediately agreed to raise havoc for her on the mission when she asked and even smiled at her again. He also encouraged her if you talked to her in the 7th Heaven after that.
Also, the story seems to treat the "No promises" option to her invitation as canon, since he mentions their planned date during their last conversation, and
before she does. This means that at some point, he
did think about it as he'd said he would and had decided to go ahead and have that dinner date with her. And when she admits her feelings for him during their last conversation - "I just... really wanted to believe... that we..." -
he does not shut her down. He
affirms her feelings by acknowledging them and reminding her of the date they had planned to have together. It can be seen as an indirect way of telling her he liked her, too. One that she picked right up on, as her happy smile shows.
You might be interested to know that Clessie videos on Youtube are getting just as many - and in some cases even more - views than Cloti and Clerith videos. In fact, one of the videos showing how to get Jessie to kiss Cloud has literally
over a million views. That's more than any single Cloti or Clerith video. It's even more than the highest-viewed Cloti video (which is at almost 900k views and was posted at about the same time as the Clessie kiss video). So obviously people are seeing something in the pairing.
I don't know how you can say Jessie was fortunate when she was basically tossed aside after Chapter 4, though. There could've been scenes showing her and the rest of the gang while Cloud was stuck with Aerith so we'd be able to see them react to hearing what happened to him and see how they found out about Corneo and the pillar. There could even have been a playable segment or two using Barret and/or Tifa with them so they wouldn't just disappear for half the game.
If she does come back for Part 2, there's nothing stopping SE from developing her into a viable third option, especially given her history at the Gold Saucer and the date event itself - which if she comes back, she should surely get a Gold Saucer date of her own with Cloud because she was in the very play that's part of that sequence. It would give us a further glimpse into her backstory and character as well as give her and Cloud a chance to actually share that date they never got to have in Part 1.
And as for the trope, it's not 1997 anymore. SE doesn't have to stick to things as they were then.
So I'm picturing whatever Gold Saucer date event(s) happen in Part 2 would be more of the same where the character actions won't contradict one another which makes the most sense story-wise, anyway. (Also, I'm a girl~ 
)
