Well this film was predictable to say the least. The biggest surprise I got was when I found out the protagonist was male. I'm not saying this to offend in any way, I think this is one of the things that was done right, the casting of the main character. He is a caricature of what most guys have experienced at some stage in their youth, offering a chance to laugh at ones teenage confusion. However I miss a certain emotional connection to the character. Why should we care about him? Okay he has problems getting the girl he likes, but then again he doesn't really care in the end weather he gets her or not, as long as he gets A girl.
So how could you have made us relate to the protagonist more? Well I think you should have dropped the whole "Shawn of the Dead" style planning montage, for some actual character interaction. This would open a whole new platter of possibilities of where you could have taken this short.
As it stands, this film has a few nice camera tricks. Some match cuts, but nothing that redeems the emotionally stale story. I'm sorry but even comedies should make the audience care what the outcome is. Let me recommend you watch Groundhog Day with Bill Murray. A great example of laugh out loud comedy with emotional substance.
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