seeing as how I had gotten his route many times on accident (trying for james and I keep ending up empty handed) He will ask you out the same day you would ask him if you play his route correctly
I'm trying to get the Adam route. Is anyone supposed to ask you out or vice versa? I make sure to get Jake to go to Q&A instead of Adam but when Jake comes out to Hannah the option of asking him out comes up. And as for the Carlos event on September 24 the MC just goes to talk to James. I don't even want James. Then come October Carlos doesn't come out. I've gotten it to happen a few times but I end up with no one at the end.
Adam won't ask you out until the very end of the game (after the usual ending; when you return from Christmas break), but getting Carlos to come out to you early is a requirement. If he doesn't, then you can't get the ending.
You also can't be dating anyone else throughout the entire game.
It sounds like you're not getting close enough to Carlos if he isn't coming out to you. Spend more time with him and Adam, but avoid the four freakout points.
(The James conversation is fixed if it hasn't happened yet, so you might have some luck doing it sooner at a time when you can't otherwise spend time with either Adam or Carlos.)