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See to me, it is a play on the trope. Especially as the unconventional narrative of Frozen/Frozen 2 does not really make Kristoff the "romantic lead". Technically he is, but the relationship spotlight is always on Anna and Elsa. They are each others "true love". Yes, Kristoff is a bit worried about being good enough for her, but that is the C-plot and that is played for some laughs and a chance for Kristoff to finally get a song (and what a song it is). We know Anna loves him and she'd say yes in a moment, him being Cinderella be damned.
I find the "shenanigans" clever as they are focus on Anna's insecurities of losing her "happily ever after" from the first film. Anna is preoccupied with trying to not lose her sister again, and that is where her full focus goes. At least twice Kristoff tries to propose, and twice Anna is too concerned with Elsa to notice. That to me works really well, because much like the first film, while it is using a trope, it is using it to advance the main narrative of the film, which focus is not the trope, but the inverse of it. Also I think it is crucial that Kristoff isn't jealous. If there is any "conflict" in their relationship, it is that Anna spends the majority of her time having panic attacks over her sister. But that never crosses Kristoff's mind, because this group is all family, and they care for one another completely. Kristoff continues to be the best Disney boyfriend ever, while the tale itself continues to focus on the main point of it all. The sisters.
It just comes off as a standard use of that trope to me. Yeah, it should about the sisters first and foremost, but that entire subplot felt like badly forced conflict for ''reasons''