Today's the day when Faye remembers why she tries to avoid having conversations with Pintsize, I suspect. His life and his problems push her 'weird-o-meter' needle a bit too far over to the right. Seriously, though, I suspect becoming entangled in this matter may reassure her that, no matter how odd her relationship with Bubbles is becoming, she's still got
mainstream problems compared to a certain robot copper.
For your information, Claire was MUCH more supportive than you!
-- Pintsize
I can't help but wonder why Pintsize was expecting anything different from Faye. I mean she pretty much is the living avatar of 'spiky and sassy', so 'supportive', especially of
him isn't something that you'd expect! If anything, sticking up for and trying to protect Roko is more in character for her!

Has Winslow ever shown any sign of sexuality?
FWIW, I consider Winslow to be entering adolescence for a variety of reasons. The answer to the question of his alignment is 'wait and see'.
P.S.Pintsize was very upset that he didn't impress Roko before and he seems to be very keen to have a second chance now. Either he intends to get the coveted 'worst date ever' spot or he really does like Roko and we might be seeing him about to attempt a real relationship for the very first time (the mind boggles at that, by the way)!