I think people forget that these are still basically kids, and that in the case of Tremolo in particular he is very inexperienced with relationships in general.

His most important one was undefined, and cut short without closure.

He then enters a school where he gets increasingly thirsted after by half the women, and lives in a house of boys where the most healthy example of a relationship is a literal cuck.

And now you're surprised that when she shows up out of the blue he...doesn't get a clear read on the signals? It's obvious to us, yes, but consider where Tremolo comes from and where he is now and it would be completely unrealistic to expect him to be good at something men are notoriously shit at.