Several reasons why this doesn't hold up.
The "romance" was creepy and rushed. How old was Caron when she starred in this movie? About seventeen? Eighteen? Twenty at the very oldest? The age difference between the two is definitely apparent on-screen despite how youthful Gene Kelly looks for his age. I never had this problem with the Reynolds/Kelly pairing because their characters were in tune. Kelly just comes across as a stalker here. Caron's acting doesn't help. This is not how I like my Gene Kelly! And was it just me or did she seem to reciprocate his feelings waaaay too fast? I'd be pissed off for a while... I liked the idea that Gene was a bit of a giggolo to his benefactor, but of course this could never be explored because it was 1951. I loathed his out-of-work musician friend who seemed only to appear in the movie to annoy the hell out of me. He was an excuse for another (boring) musical number. This movie is worth watching for the finale, but beyond that it's so abysmal.
A good traveller has no fixed plans, and is not intent on arriving.