WESLEY: The first week that I was there, I went and met Boothby.
PICARD: How is old Boothby? I hope he didn't tell you a lot of stories about me.
WESLEY: He didn't remember you, sir. At first. I found an old yearbook photo and he remembered you right away.
"The First Duty" implies that Boothby remembers all of his previous protoges. One hopes that he was having fun at Wesley's expense.
"Found an old yearbook photo"? There are archives of physical yearbooks at Starfleet Academy? Wouldn't the photos be in a database accessible by every PADD on campus?
WESLEY: Sir, what do the initials A.F. stand for?
PICARD: A.F.?
WESLEY: Boothby said he caught you carving those initials into his prized elm tree.
Memory Alpha has nothing about this A.F. person. For romantic relationships they only have Lwaxana, Vash, Kamala, Nella, Anij, and Beverly. Notable omissions are Penny, Marta, and Philipa.
Even if "A.F." is a pseudonym for one of these women, he didn't know any of them besides Marta as a cadet.
ROBIN: When your parents are the only plasma specialists in the sector, you do a lot of travelling around. We went from base to base to base.
Plasma specialist doesn't seem like an on-call sort of job. You'd want one of those anywhere there is plasma.
WESLEY: Don't you think that's a little strange? Everybody playing it all the time.
ROBIN: It's just a fad. It's here this week. Next week we won't even know it existed.
That line stuck with me. I even established it as the page quote at TVTropes for the trope
Flash in the Pan Fad.
WESLEY: Yeah, we could hook it up to one of the computers. The medical programs in the lab can be set up to emulate human responses.
ROBIN: I noticed it uses a visual interface. We could connect it through an optical sensor.
I'd nitpick this, but if it works on Geordi I guess The Game is more sophisticated than it looks.
ROBIN: The cuts are precise. Look how clean the edges are. Computer, increase magnification, factor four.
WESLEY: Only two people on board know enough about Data to do something like this. Commander La Forge and my mother.
I'm always skeptical about "only X people on board could do this" statements. Surely there's another engineer on board who has mucked around with Data's systems.
(Alyssa is in the lift, playing the game)
Chakoteya uses last names for everyone else, why not "Ogawa" here? How many people who aren't uberTrekkies like me even remember that her first name is Alyssa?
The Fiver
La Forge: Commander, I'm sure you know Ensign Lefler here. Her work is outstanding.
Riker: Hmm... a good-looking, intelligent young female ensign whom we've never seen before....
Lefler: I know, I know. I've got "love interest" written all over me.
No kidding.
Wesley: I can't get Data reactivated.
Lefler: Did you check the "off" button?
Wesley: Don't be ridiculous. As if Data has an "off" button.
At this point even if Data didn't have an off button, you'd imagine the crew would've found something to neutralize him.
Picard: Only Wesley stands in the way of our evil conspiracy. There's no way this can fail.
All: Mwahahahaha!
Riker: Actually, sir, Wesley usually manages to stop this kind of thing against unthinkable odds.
Picard: Don't interrupt the evil cackling!
Hehe.
Memory Alpha
* The crew went to the effort of making the suite on Risa match the Risan asthetic established in "Captain's Holiday". I'm surprised that they bothered, Risa wasn't a big deal yet.
* Data promise Beverly that he wouldn't mention the dancing lessons, but he told Wesley here. I thought Data couldn't lie...
Nitpicker's Guide
* Phil is incredulous that Will only learns of Troi's chocolate addition now.
* He's surprised that the Sadie Hawkin's Dance still exists. Don't women ever ask out men in the progressive twenty-fourth century?
* Phil only brings up the differences in Worf's brain chemistry, but I must also bring up the Vulcans on board. Wouldn't they do thorough tests on the mental interface on this thing before using it?