Sleepwalk With Me
Have you seen Mike Birbiglia's movie Sleepwalk with Me? I loved it so much I watched it twice within a 12 hour period. It beautifully discusses relationships, marriage and most poignantly the struggle to realize your dreams and has the same candor as This American Life stories (which only makes sense, since it was co-written by Ira Glass). If you haven't seen it, I highly recommend it.
Here's a really great tidbit from the movie: "It wasn't going so well, but I kept telling myself that it was. I think to be a comedian you have to be a little bit delusional. particularly starting out, there's just so much failure. And amidst that failure you have to tell yourself that it's going quite nicely, because if you didn't, you would just never get on stage again."
And a hilarious but beautiful take on love: "Falling in love for the first time is such a transcendent feeling. It's like eating pizza flavored ice cream, your brain can't even process that level of joy... I really feel like our whole lives no matter how low our self esteem gets there's always a part of us that thinks 'I have a secret special skill, that no one knows about.' and eventually, we meet someone who's like 'You have a secret special skill!' and you're like 'I know, so do you! Let's eat pizza flavored ice cream together!' And that's love. It's a mountain of pizza flavored ice cream, and delusion."