Why are computers in movies never like real life?

I don't get your the connection between your title and your actual comment.
But Jules' intention wasn't for the email to be sent, just viewed by Michael.

And he probably meant the emails in his draft that he didn't get a chance to send.
Meh.

"Do you even remember what you came here to find?"

Who knows what the workflow was in 1997 and I don't find it impossible to believe that a executive wouldn't be sending his own emails. It's 2015 and many of the execs I've worked with are so computer illiterate it's astounding. Now go back to 1997 and think about that for a few minutes.

I think it would have been more likely back then to have dictated a letter and have someone type it up, possibly review it and then have your secretary send it out.

Movies tend to be very generic. No one ever orders a bud light, or a Molson on TV, they just say "I'll have a beer". Where can you go in real life and say I'll have a beer, without the waitress staring at your like you're an idiot?

Phone numbers are always 555-1234 or something like it....so the email thing was probably the same way. Instead of coming up with an actual email address, they kind of bypassed it. Weird yes, but it just seems to be what they do in movies, they don't bother coming up with specifics. Especially in a rom com that isn't meant to be the next oscar winning film.

As far as him not sending out his own emails, I thought that was weird too, but like others said, most top bosses don't know how to smooth things out. He probably wrote the pertinent information that needed to be said, and it was his secretaries job to read it over, make it sound better and then send it. And, it made for a convenient way for the email to be sent when it shouldn't have been. Again, we're not supposed to question the details in movies like this.