I think he would have wanted to impress her and would be intrigued as she would have shown magic in a way that is not to impress him through frightening ways, but in a beautiful way, not to mention her demeanour would confuse him as it would be so different from how Mrs Cole interacted with him.
But that's a fallacy many can fall in, especially as it can (unconciously) help them to conceal their regrets, their own mistakes. Distance can have its advantages when dealing with some situations, but it can also trick people into false sense of knowing how to react or to act.
You are right that Tom was just a boy, one that was alone and raised in one of the least recommended places for a child. And Dumbledore... He was in his "median" period where the guilt for what happened to his sister and his family as a whole was likely the strongest and where the shadow of Grindelwald was further stronger (and while "The Fantastic Animals" had their issues, the idea of the blood pact is an interesting twist to me to show how far Dumbledore and Grindelwald went in this fateful summer). I think that in a way, Dumbledore was projecting those elements on Tom.
And of course, when Dumbledore shows the memory to Harry, there is the fact that almost 60 years had gone by since the first encounter, meaning the memory is also altered by the personal feelings and impressions on one hand and on the other, as much as Dumbledore might remember things, those memories are also biased by whatever experiences and interactions he had known afterwards.
Really, Dumbledore had a bit of a bad entrance also because he was the older man in this case. Immediately an association with a doctor/professor... I don't like the fact that in fanfiction it is presented that Tom would react similarly to Harry - a time traveler... No, Tom would not behave the same towards Harry at all . Harry, who was a young adult with untidy hair and lack of typical decorum, would have a different reaction than Dumbledore. Tom wouldn't associate Harry with a representative of a mental institution at all.
My SI would also would have an easier time because Tom would be surprised by the young woman in an elegant dress who visits him at the orphanage.
You are totally right. I know why Dumbledore did it, because otherwise Mrs Cole wouldn't have allowed him to visit the orphanage, but the moment he entered the room (and he could have confused Mrs Cole or waited for her to leave and turned her back), he could have change his clothes with a move of his wand, which also could have been a better way to show Tom he wasn't alone without using a terrifying move (burning-like cupboard). I think in this case, it's a comprehensive overlook as he couldn't assume Tom was conciously using his magic, even for harmful (albeit in a defensive manner) reasons.
You are right on both the time-traveller Harry and your SI. I think part of the issues with fanfictions is the temptation to recreate situations, even when the circumstances and context have shifted. The fanfiction depicting Tom reacting the same way with a time-traveler Harry as with Dumbledore is the same as the Red Wedding occuring in many fanfictions or Jon being raised as king of the Seven Kingdoms once he found his Targaryen legacy (and often turning back on his Stark raising) when there are many obstacles and challenges to overcome (and having a dragon IMO may make things easier, but also enhanced those issues of legitimacy).
That would be funny... Time traveler Harry goes to the orphanage and expects to be treated like Dumbledore... and Tom immediately becomes full of joy, asks him if he is family - cousin or stepbrother... or his father sent him.
How do you think Tom felt about the closet/being told to give things to other orphans...
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