He didn't type up all those love letters

The film: Sex and the City: The Movie
What happened: Sitting up in bed, Carrie (Sarah Jessica Parker) reads a book of love letters by famous men. She complains that John James "Big" Preston (Chris Noth) has never written her a love letter, and that e-mails don't count. Later on in the film, after Big ditches Carrie at the altar, Big sends Carrie an e-mail which makes no effort whatsoever to win Carrie back. Carrie orders her assistant to place all e-mails from Big into a place she won't have to look at them. After a while, Carrie decides she does want to read Big's e-mails, but her assistant is not around. So Carrie guesses her assistant's password and finds that Big has e-mailed her, one by one, all the love letters from the book she had been reading. Carrie is touched by the gesture and goes to reconcile with Big.
Why it makes no sense: So if Big is really such a big-shot, does he really have time to be typing up love letters from some book? If the book is not readily available in some electronic format he can just copy and paste from, it would either have to be scanned in and text-recognized or typed up. Big doesn't have the time to type up an entire book, nor to scan the book a page at a time (or maybe two pages at a time), but he certainly has the time to order an assistant to make it happen. Either way, the gesture is cheapened by the intrusion of a third person. I guess it really has to be the thought that counts here.
As for the easily-guessed password of Carrie's assistant, it shows a lack of tech-savvy on her part, but is entirely realistic as there are people in real-life who choose passwords that are very prone to a dictionary attack.