Catfish
This film was especially applicable to our generation. It's about a guy who starts a relationship online through Facebook and it escalates into an obsession. The relationship exists purely online and over the phone for over 9 months. The style of filming is mostly hand-held and so the viewers can feel like they are right there with the characters. It also tells the story chronologically and so the viewer knows just as much as the characters of the film do at the time. In the end, the guy discovers that the woman with whom he was having a relationship online was a complete fake and had created a completely false identity for this relationship.
The director managed to make me care because the whole I had the suspicion that the girl wasn't completely honest with him because if that was so then there wouldn't be much of a story for a film. Even with this suspicion, I was hoping that I was going to be wrong because I didn't want this to happen to the guy. The reason that I cared for this guy is because I have some friends that have gone through a very similar experience with online dating as I'm sure most people of this generation know someone that has gone through something similar.
I think the point of the film is to show the experience of online dating as it develops from the beginning and the risks that are involved with it. I feel that this goal was achieved because it made me personally feel that online dating is rarely a smart option.