* Why does everyone take Tom's asking Autumn out as a sign that he learned nothing or a HereWeGoAgain? Is Tom just supposed to give up on relationships and be like Summer was at first?
** i take it as a sign that he had changed for the better really.
** It's the fact that the counter restarts. He's right back where he's started, the names have just changed
*** So whether or not he have better luck this time or make the same old mistakes remains unrevealed.
** Because of the similarities between how he perceived Summer, and how he seems to perceive Autumn. Both girls share with him some sort of quirky taste, very specific feelings on specific things, as well as seemingly having a touch of 'destiny' about them in his eyes. These are not good enough traits to decide someone is 'the one', but that's what he did with Summer anyway. It seems he's about to do the same with Autumn. And, yeah, the counter resets.
*** Yeah, but she's ''Autumm'' as in, what's next of Summer, not the same. Symbolically it very clearly implies evolution and transition and thus, hopefully, improving.