Good stuff man. I like that style of improvisational acting. It's an actual movement called "mumblecore" where each scene has a basic outline (Jenny breaks up with Greg) and the actors bring it to life with their own character interpretations. I think a recent example that was pretty good is the movie "Drinking Buddies". All the dialogue just feels so much more natural and real, because it's all somewhat spontaneous.
I'm by no means a great filmmaker. But here's some very basic random tips after watching yours.
- Invest in a better audio source. A shotgun mic or something. It will make a big difference in the quality. Nothing screams "amateur" more than onboard audio from a camera.
- Nothing wrong with camera movement, but you might want to steady it a bit... even if that means sticking it on a tripod
- I love musical transitions. I use them all the time. I like that it creates literal movement and drives the story forward. But careful about not making them too long. It's somewhat unnecessary. I think your first one was about 2 minutes. I've seen short films shorter than that. Keep that in mind when you think about pacing.
- Speaking of music, be careful not to use copywritten work. It's probably fine for fun productions (I've done it before), but if you ever want to do more with your films you're going to have to use royalty free music or use original compositions you have the rights to.
- Think about how you are framing your shots. A basic understanding of "Rule of Thirds" will help: http://en.wikipedia.org/wiki/Rule_of_thirds
Have a basic understanding of the 180-degree rule: http://en.wikipedia.org/wiki/180-degree_rule
... You can make some of those dialogue shots a lot more interesting if it's not just the person looking directly in the camera framed right in the center of the shot. Think of those basic "over the shoulder" shots you see in most movies.
Just some really general feedback. All the technical stuff is far less important than just telling an interesting story. You should totally think about finding some of those film race competitions in your area. Attempting to conceptualize, write, cast, film and edit a 4-7 minute short film in only 48 hours is a ridiculous undertaking and the results are usually predictably awful, but it's a a ton of fun. Here's one I did last year for the Seattle 48 hour Film project:2013 Requirements:
Character: Gino/Gina Asplund, a Barista
Line of Dialogue: "There must be something in your ear"
Each team picked a genre out of a hat and we got stuck with "Fantasy"https://www.youtube.com/watch?v=qIrqtmzItPA
There are far far better filmmakers than myself out there (a couple on this forum, I think), and a endless amount of free information online, but if you ever have any questions or anything, feel free to send me a PM. I'm self-taught in all this stuff. You'll get better each time you make one.