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Name That Episode, TNG Edition...

Hollow Pursuits?

Clue 1. Someone else gets what he wants eight years later.
He wants Troi, and Riker finally gets Troi 8ish years later?

Clue 2. Badly phrased
Picard accidently calls him "Broccoli"

Clue 3. Second time out of way too many
Barclay is late for Geordi's meeting, after being late to the storage bay earlier.

Clue 4. Knows them too well
Barclay creates charicatures of the senior staff on the holodeck, and he's captured them all brilliantly(in hyperbolic fashion).
 
Hollow Pursuits?

Clue 1. Someone else gets what he wants eight years later.
He wants Troi, and Riker finally gets Troi 8ish years later?

Clue 2. Badly phrased
Picard accidently calls him "Broccoli"

Clue 3. Second time out of way too many
Barclay is late for Geordi's meeting, after being late to the storage bay earlier.

Clue 4. Knows them too well
Barclay creates charicatures of the senior staff on the holodeck, and he's captured them all brilliantly(in hyperbolic fashion).

You have been caught making a sex fantasy out of your professional acquaintance.
 
Clue 1. Someone else gets what he wants eight years later
Clue 2. Badly phrased
Clue 3. Second time out of way too many
Clue 4. Knows them too well

Clue 5. Not usual weather for that location
 
Elementary, Dear Data?

Correct!

I thought I was giving it away with clue 2.

Clue 1. Eight years later, the Doc gets his mobile emitter and freedom from holodecks.
Clue 2. Geordi’s request was badly phrased.
Clue 3. Second holodeck malfunction.
Clue 4. Data knows the books too well for it to be a mystery.
Clue 5. Moriarty creates weather on the holodeck unusual for London.
Clue 6. Geordi and Data share their hobbies with each other.
Clue 7. The question is whether Data can solve a mystery he hasn’t memorized.
 
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