Wain seems to bring an unabashed earnestness and uncynical message to many of his films - something I really respond to.
I love that he takes time to develop the characters and their relationships, and that most of the comedy comes from the circumstances and mostly the delivery. It is a good thing that he has built this troupe of very talented comedians like Jane Lynch, Ken Marino, Joe LoTruglio and Paul Rudd who are very reliable.
When I first saw it when it came out I wasn't as taken with it, but revisiting it now everything just clicked. I loved this film and think I'll like it more and more on rewatches. Overall it's my third favourite out of the four films of his I've seen, but that says more about Wain's career rather than the film itself.