I prefer longer engagement sessions. They are more flexible, more fun and in the end produce better photos because everyone has some time to relax and act natural. Plus, a big thing for me is really getting to know my couples and we only have so much time to do so before their weddings, so having a nice long afternoon to do just that is ideal.
As a photographer, I am always encouraging my couples to get out and do something new. Sure, part of it is that I like to travel, take long drives and explore, but the other part is that I know adventure tends to bond people and opens up that kid center of the brain where we let our guards down and simply enjoy an experience. When those things happen, my job stops being about creating moments and just capturing whats going on in front of me, which is what I absolutely love to do.
Sure, the short session in a pretty field can be nice, but unless that pretty field has some sort of significance to you both, your photos aren't going to have that same pop. And do you really want pictures of yourselves in a place that thousands of other couples have pictures from that year alone? If your answer is no, then give some thought as to what places hold meaning for you or perhaps even a place that you've wanted to go and just haven't. In the end, you'll be more in love with your engagement session because it will have a story and a personal attachment.