Raleigh glancing over all of Margot's affairs to focus on her hidden smoking habit seems out of place until you realise he's spent several years with a woman he only just found out he knew absolutely nothing about.
Harsher in Hindsight: There's two of these moments in the scene where Ritchie Tenenbaum attempts suicide by slitting his wrists with a razorblade. The character of Ritchie is played by Luke Wilson, whose brother Owen (who not only plays Eli Cash in the movie, but also co-wrote the film) attempted to kill himself in late 2007 in a similar manner; Owen had also intentionally crashed his vehicle, resulting in facial bandages, necessitating Wes Anderson write in such a backstory to Wilson's character in that year's The Darjeeling Limited. Furthermore, this scene is soundtracked by "Needle in the Hay", a 1995 song by alternative folk musician Elliott Smith. Two years after the film was released, Smith succeeded in killing himself (although with a knife, not with a razor blade).
The next song on the soundtrack is "Fly" by Nick Drake. Granted, the filmmakers knew Drake had taken his own life...but coming right after Elliott Smith (who they hadn't known about), it adds to the creepiness. Word of God says "Fly" was chosen more-or-less randomly, as it happened to be playing in Wes Anderson's Walkman (when he was working on the scene, or first viewing the rushes...something like that).