Inspect my logic here in this TC

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here , for the second blank, greg’s logic is , it is previously referenced (becoz "unfortunately signifies something negative and thus the idea of second sentence should contrast the first one, and "does not make " does the job, so the blank cannot be negative), i thought unfortunately and however are both negative an thus the blank needs to be +ve.
Is my approach correct?

NO, consider one of them as just emphasis given to contrast. Or think unfortunately and however acts as a single word there.
However is just an emphasis given to unfortunately.
The contrast is not with the blank. The contrast is between ‘obsessively’ and ‘no intimacy’. Since, there is already a contrast existed, we just have to put the word there that’s previously referenced.

So when two negative words come next to each other (in this case "unfortunately and “however”) if , they always have to not contrast each other, then how do I figure it out?

i. unfortunately, however ______ , {sth}
ii. unfortunately, however, _______.
This is how I identify.
If you don’t see anything after however before the comma, however isn’t a contrast (just an emphasis) like in the second one.
In the first one though, however acts as a contrast to {sth}
as well as you can say, it cancels out with unfortunately.

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Spot on, thanks a lot, i understand it very clearly now!!! :))))))

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