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In Harry Potter and the Goblet of Fire, when Harry is looking at Dumbledore's memories, Harry sees a scene involving young Bertha Jorkins and Dumbledore:

"He put a hex on me, Professor Dumbledore, and I was only teasing him, sir, I only said I'd seen him kissing Florence behind the greenhouses last Thursday...

"But why, Bertha?", said Dumbledore sadly, "why did you have to follow him in the first place?" - Chapter 30

Who had Bertha spied on (other than Florence [?] of course, who is already named) and why does Dumbledore seem so troubled by this?

It can't be Riddle for a few reasons:

1) the unnamed character was kissing somebody. Book 8 aside, there is no indication that Riddle ever harbored emotional / physical feelings for anyone

2) Bertha did not attend school with Riddle, but rather Sirius Black, who attended well after Riddle's departure.

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    Snape? Potter? Black? Lupin? Pettigrew? There's zero context to that event, it just gives us a glimpse of Bertha's personality, so it could have been anyone we know or anyone we don't. – Radhil Oct 28 '17 at 14:05
  • I think he's troubled by her tendency to do that sort of thing and the person in this case is irrelevant (it could be any unnamed Hogwarts student). – elrond Oct 28 '17 at 14:53
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It's unclear, but it didn't matter - it was to show that she was nosy.

When Dumbledore was looking at the memory of Bertha in the Pensieve, he was trying to figure out the disappearances connected with the Dark Lord. It's likely that Dumbledore, as Sirius did, suspected that Bertha's dim nature and proclivity toward gossip could lead her into trouble.

“He put a hex on me, Professor Dumbledore, and I was only teasing him, sir, I only said I’d seen him kissing Florence behind the greenhouses last Thursday …’

‘But why, Bertha,’ said Dumbledore sadly, looking up at the now silently revolving girl, ‘why did you have to follow him in the first place?”
- Harry Potter and the Goblet of Fire, Chapter 39 (The Pensieve)

The only information we have on who Florence could have been kissing is that it's a male who was at Hogwarts when she was. (We can probably safely presume it's a fellow student, since teachers are unlikely to hex a student over being caught kissing.)

If we presume it's a fellow student, then it still could have been any boy who was at Hogwarts when Bertha was sixteen. There isn't any more information on Florence, she's never mentioned again, so there's nothing that indicates who might have wanted to kiss her. She was a few years above the Marauders, so it's possible it could be one of them, though depending on how far ahead she was of them, they might be too young for kissing. It's certainly not Tom Riddle, since as stated in the question, he definitely wouldn't be kissing anyone and didn't go to Hogwarts at the same time as Bertha.

Dumbledore's troubled by it since he likely realized her curiosity was relevant.

The main thing that people keep referring to about Bertha Jorkins is that she had a penchant for gossip. Sirius remembers going to Hogwarts with her, and that's what he remembers most about her. He also realized this would make her easy to lure into a trap.

“Listen, I knew Bertha Jorkins,’ said Sirius grimly. ‘She was at Hogwarts when I was, a few years above your dad and me. And she was an idiot. Very nosy, but no brains, none at all. It’s not a good combination, Harry. I’d say she’d be very easy to lure into a trap.”
- Harry Potter and the Goblet of Fire, Chapter 19 (The Hungarian Horntail)

Dumbledore says this to Harry about curiosity, when he sees Harry had used the Pensieve, right before Bertha appears in it.

“Curiosity is not a sin,’ he said. ‘But we should exercise caution with our curiosity … yes, indeed …”
- Harry Potter and the Goblet of Fire, Chapter 39 (The Pensieve)

After that, he sees Bertha in the Pensieve, and asks her rhetorically why she had to follow him at all. It certainly seems like Dumbledore, just like Sirius did, realized that Bertha being both dim and nosy was liable to make her easy to trap.

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