I used to love this movie
My mom would watch it all the time in her sewing room (sometimes the living room) when she wanted a good romantic comedy to entertain her, and I liked it too....as a kid. I even listened to the soundtrack on my Walkman.
But frankly, as I got older, I realized that this movie isn't as great as I thought it is. Sam and Annie only meet twice in the whole movie, and spend most of it trying to figure out that they're meant for each other and not the people that are there with them in their towns. (I personally would never date a pan-allergic person like Walter, though I like the actor).
I like romantic stories where the couple spends time together, getting to know one another, having adventures together, and bonding. It's no fun to see them apart for 90% of the movie and pining for each other.
So it's a nice movie, but I would not watch it as much as I used to.