Lloyd (John Cusack) the optimist, works up the courage to ask out Diane (Ione Skye), the class brain, even though everyone tells him he is crazy for even trying. Surprisingly, she says yes and soon the two are spending a lot of time together, much to her father's distastes.
A tale of first love that is super awkward, so much so that it makes this film so real and heartfelt.
I love the fact they had Joan Cusack play the sister of Lloyd who is really her brother in real life. That definitely tickled my fancy. And that this was originally written as a novella instead of as script and from that the story was developed. It was refreshing that Lloyd had a core group of female friends that he hung out with and asked for advice, when he did go to the guys he wasn't disappointed, they were jerks and unhelpful, just as he expected.
This is a must watch for everyone. If only there were Lloyds out there in the world, it would be a better place filled with men not guys.