The ride I do most often is an 11 mile out-and-back that I can sneak in at the end of a work day. Since it is 900 feet or so of elevation gain going out and 900 feet or so of elevation loss coming back, the two directions on the same roads are definitely different experiences.

Loop, out-and-back, point-to-point, lollipop, all can be great, all can be dull as dirt, all can be easy, all can be killer, depending on a number of variables (including who you are doing the ride with). I say: don't over-think it. A fun ride is a fun ride. Enjoy.