First attempt at a music video / short film; comments?

It's good. It didn't really come off as an amateur video and goes well with the music. A couple of small things though. I was enjoying the progression from the beginning of the video until about 90 seconds in, and then some of the scenes from earlier repeated again (at least the earlier location was repeated after moving away from it over the course of a minute) as in 0:40 and then 1:42-1:43. I would take shots like at 1:43 and group it with the one at 0:40 instead of dispersing it later in the video because it interrupts the continuity of the scene progression. There's a few other places where that happens but that's just me being technically critical.

Also I noticed a single-frame edit at 2:28 of black (between the notebook shot and phone booth) that needs to be taken out. Overall the video is good and I liked it.

It isn't a huge issue, I'm not sure what you used to edit but I've encountered this while using FCP X (although the rouge single frames usually aren't of a black generator but rather a random screencap from one of the other scenes)

Solid first attempt. One piece of advice would be from an artistic point of view. While it looks like you're going for an old home movie look the composition doesn't really mimic it. Everything looks very stable and cleanly shot. One thing I'd try for next time would be to do all those shots hand held with the stabilization turned off and get in tighter to your subjects. If it's supposed to be a home movie then try shooting it like one. If it's a friend shooting it I don't think they'd be that far back with a tripod. Making it look more spontaneous and personal will help connect the viewer to the subjects and what they used to have, giving everything a bit more emotional weight. Also, a different color timing for those flashbacks would really help. Something a little more washed out and maybe adjust the motion a little bit to simulate the old 15fps 8mm films. All of that will help define the flashback from the present. Overall a very nice first video. Can't wait to see future videos! Nice work!