I think I saw it when it first came out but I don't remember much of it. This was back in the good old days of AOL instant messenger. I think this movie and You've Got Mail are the two movies where the characters instant message each other to move the plot.
It's a romance movie so the predictability runs at like 110%. Somehow that genre gets away with it.
Unexpected elements: It's a romance between seniorish citizens, and so we get a bunch of senior citizen nudity and a senior citizen sex scene that's a little cringey. Dianne Keaton spends a good 10 minutes wailing hysterically in front of her computer. Is it supposed to be funny? It has that Seinfeld-esqe element where the character is in distress but the audience isn't set up to empathize. Maybe there's Charlie Chaplin music playing to keep the mood light. And I wonder if it's a little bit sexist to show that the woman goes crazy while the man is more carefree about their odd relationship.
The movie has a lot of witty dialogue, which you don't expect from a romance movie for some reason. Dianne Keaton plays an ultra successful broadway playwrite with a super nice beach house, but she just steals dialogue from her personal life! Shakespeare did the same thing in Shakespeare in Love. Maybe that's the secret to writing good dialogue: steal it. I'll have to think about that. I do have some clever friends I could leech off.
I did like how Keanu Reeve's plays the "other guy" who gets rejected (whoops, that was a spoiler! Sorry.) and ends up presumably unhappy, while being shown as a perfectly nice guy. Most ex-boyfriends in movies are jerks who cheat on their girlfriends or bully other people, just so that you don't feel bad for them when the girl is stolen away. But in this movie you do feel a little bad for Keanu Reeves. On the other hand he's a male doctor, and I think they tend to get a lot of women. I'm sure he'll be fine.
Doctor: Do you realize that a severe anxiety attack can masquerade as a heart attack?
Harry: So I'm nuts! Perfect. The one thing I'm not taking pills for.
(Having had my own anxiety attack recently, this is totally true.)