On a per app basis definitely yes. Globally, not so much.

Any change in your routine would show how dumb the phone is.

BTW, what you describe is what is happening right now when you are on-line. If you use a Google web app like Gmail you will notice that the ads you are served change relative to the time of day and what is mentioned in your e-mails.

I do wish individual apps would get smarter though. For instance a media player that generates a random playlist based on the first song you pick from your library. If it's a head banger tune it serves you head banger tunes. etc.

On-line apps like Pandora do this now based on seeded information.

Why couldn't the same be done with a local media player?