When dealing with others you find that some people have a continuum of parameters from loose to tight when it comes to their rules of play. Some people are very easy going with few to no constraints and others are wired tightly with lots and lots of rules. There's all kinds of reasons for where people fall on this continuum, and when dealing with people, it's good to understand where they fall and why. After that, you have to consider whether their loose or tight constraints fit your needs, lifestyle and interests.
For example, you may have a friend who is bound by very tight parameters, so tight that a single misstep may throw your relationship into a frenzy. If that's true, you may narrow the kinds of interactions you have with that person. On the other hand, you may have friends who have very loose parameters, so loose that you never quite know where you'll land when you spend time with those people. You may enjoy the serendipty and surprise that goes along with loose parameters or you may decide that's too much for you. Whatever the case, it's good to think about where people fall on that too-loose to too-tight continuum as well as where you fall too.
For me, I like a mix. I find that friends who fall close to the too-tight end of the continuum seem to be very detailed oriented and measured in their approach to life. Often, these individuals introduce me to the finest that life has to offer. On the other hand, my friends who fall on the looser end of the continuum tend to be easy going and full of positive surprises--that's a lot of fun. I see value in all the places people fall. I'm open to the mix, but sometimes I err when I expect a detailed individual to loosen up or an easy going person to align themselves to tighter parameters.
The win is when you match people to the event--you find the sweet spots for individuals and groups with just right planning in ways that everyone has a good time. That's a good challenge to embrace. Onward.