I prefer to play a course for the first time either alone or with someone who knows about the course, its history, and its quirkiness. Usually I learn little about a course by playing it for the first time with a group.
I love to finish up work for the day around 5PM, on the road a couple of hours from home, stop at a course I haven't played in a while or at all, grab my clubs from the trunk, pay my green fee, and get paired up with another single out for the evening to play a quick 9 holes. Almost always the other single on the course plays frequently by themselves on a weekday evening, and they often have tremendous insight into a course, no matter how simple the course is, along with a bit of local flavor. I may never meet this person again, may never play the course again, but the experience stays with me always.
And to those of you that stop at ND, let us South Benders know, we can play a round somewhere locally. Today might not have been so good though....45 and rain!