And once this flashback's done, the trauma from that time will just magically disappear. I'm sure they will play it off as "you were just an idiot bro, get over it" and move on as if that's how you solve mental health. An arc where he actually had to go to therapy and everyone including him had to deal with that would have been a more interesting arc than this "will he, won't he (he won't, twice)" that they had after the first rejection.
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I'm getting some Rockstar 2001 vibes here...