Ok, awesome update! but is there any indication on how to actually be "officially dating" with someone, or do I just wait?
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Depends on who you're going for! Special characters have special conditions to get into relationships with them. I think there's currently a way to date the best friend, classroom harasser, and roommate/roommate's partner, but no one else.
If you're talking about a rando? Some of them just may not be into a serious relationship and prefer to be fuckbuddies, others prefer open or poly relationships, others still might want a Dom/Sub relationship. But in general just date them a bunch. Eventually you can approach them on the People menu and propose a change in relationship. Or they may bring it up themselves after a successful date. This can take a looong time, like a month or more of ingame time.
Ty, I was going for the cheerleader captain, and I already did all the conditions, only the officially dating part is left that's why I am asking. But I guess there's no update for that part yet (is there?) cause she's still dating the football star... The Cheer Captain Milestone I've accomplished so far below: