The Five-Year Engagement starts out being very funny and then just barely grazes the finish line towards the end. Obviously with a title like "The Five-Year Engagement," there's going to be some ups and downs in the relationship, but man this movie meanders. It's not that it stops being funny as there are still a decent amount of jokes to be had all throughout. This is mainly due to a great supporting cast which includes Chris Pratt, Allison Brie, and Brian Posehn. The problem is that the movie just takes way too long to get to its inevitable conclusion.
The leads, Emily Blunt who plays Violet and Jason Segel who plays Tom, have great chemistry together. Tom and Violet decide to postpone their wedding after a year of planning because Violet just got into the University of Michigan's post-doctorate program which lasts two years (they moved there from San Francisco). Honestly though, I thought the reasoning for them not getting married was quite contrived. It was literally, "let's just hold the wedding off" even though the move doesn't really seem to necessitate holding off the wedding.
Violet enjoys the move to Michigan as her career advances further, but Tom's a chef and he turned down a head chef job back in San Francisco. The best he can seem to do in Ann Arbor, Michigan is to work at a sandwich shop. His lack of career success frustrates him but he tries his best to put on a happy face for Violet. The second act kinda drags on for quite some time turning this into a two hour movie. The Apatow crew really pressed their luck doing this with Bridesmaids, but Bridesmaids was long because the funny scenes lasted longer. Five-Year Engagement just feels stuck in its own contrivances.
I've gone over this before with other movies: when you know the movie is going to end one way and it takes so long to get to that point, it's a problem. A goal for a movie like this is to make you forget that you know how it's going to end, funny scenes help that. You know Tom and Violet will finally get things right and be married in the end, I get the struggle of the five-year engagement but the reasons for the postponement are just too weak. This makes for a very frustrating watch.
I'm generally a fan of the Apatow brand as well as Jason Segel and Nicholas Stoller. I still think they overdo it with the gratuitous sex scenes that always seem to delay the third act of their R-rated movies (this includes Forgetting Sarah Marshall and Get Him to the Greek). Five-Year Engagement is mostly a successful movie, but as a classic romantic comedy, it comes up short.