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It was in the 5th episode of the 5th season of The Office.

Here is the context: Pete: That’s perfect. You know what would be even more hilarious? Remember that thing we did when Jim was in high school with his girlfriend? Tom: Right! That would be hilarious! We should totally dog her, about being an artist, never making any money!

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It means to pester or tease her.
Merriam-Webster "dog"

transitive verb:
c: to bother or pester persistently
dogged him about his grades

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  • There's another meaning which is more about insulting or abusing someone, in the sense of "treating someone like a dog". You'll sometimes hear dogging [someone] out. I think this example is meant more in that sense - it's not about generally bothering someone, it's about dragging them to make them feel bad. Dec 28 '20 at 22:33

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