In Universe, Takae and Ushigome may have bad starts with him (putting it mildly) but that wasn't the point I was making there. Just that Ushigome wasn't the first to confess her feelings to him.As much as I love Yuna, she's one of the two girls that made him this jaded in the first place. In the same vein, Takae was the first girl to actually hurt him and make him move towards his inability to actually accept their feelings.
As for the Prez, she got what she deserved, a clean rejection. You don't badger a guy into choosing between going on date with you and causing a stink with other girls through rumours and then expect them to accept your confession. The sole reason he didn't acknowledge her feelings as serious was because she did act like it wasn't serious herself, immediately trying to drag him into shenanigans when he felt sorry for her.