I've been annoyed by overly persistent LIs in these games before, but I think the problem here is a bit more subtle: it's the way Ashley and Jenny feel the need to hash this out by themselves, as though the MC is unable to handle the matter on his own. It really drives home the feeling that the MC's wishes (and by extension our choices) aren't relevant. Even if the game will ultimately give us a solo path, it sure feels like it's trying to nag us into the harem at the moment.
It would be a very different matter if the meeting only happened when the MC had given a non-committal response to each girl; in that case it's less going over his head and more trying to solve a problem he seems stumped by. But this happens even if he's explicitly told Ashley she's the only one for him, or that he only sees Ash as a friend. At a certain point the game needs to trust us to decide what content we want to skip.
It also makes the girls look more than a little delusional when this is their priority after Adam has threatened the MC's life and all but signed Valery's death warrant, but I've already ranted about that.
I've never had an LI in these games talk to another main girl I've rejected, telling her she loves the MC, but then, in the end, it's like may the best woman win. I must've had my MC tell Ashley what? 4 times that he loves her and she's STILL worried about the MC's feelings towards Jenny or even Jenny's feelings towards the MC? Who gives a fuck!
Be happy I chose you and leave the other girls in the dust. Don't worry about Jenny's feelings or what SHE wants, worry about what YOU want. Her bullshit insecurity crap is ruining it. I mean, the dude gets kidnapped, beat to shit, could've been killed, and on top it all off, she gives up her virginity to the guy, probably because he'll be leaving school (possibly) soon, and yet she's fucking worried about Jenny's feelings?
Like I said earlier today, how many times do I have to reject Jenny? How many times do I have to tell Ash that I love her? I'm starting to lose count on both at this point.
I neglected and ignored fucking everybody else in this game. I don't see Rebecca, Jade or Valery lining up at my MC's door asking "what about us?" Nor do I see Sung and Vicky doing the same. I've ignored them just as much as Jenny. I've ignored Aurora and Elizabeth.
But noooooooo! Fucking Jenny hasn't gotten the point by now and on that matter, neither has Ashley?
Get a clue Jenny. GO.THE.FUCK.AWAY!!!
Get a clue Ash. I CHOOSE YOU!
How many times do you have to tell these girls how the fuck you feel?
And on that note, I'm going to bed