Should I bring up an issue with my roommate / best friend a week before we leave for winter break?

Hi there.  Thank you for this questions.  I can understand how this can be a stressful item to think about.  Usually, talking things out can feel better, even if we do not end up with the exact solution we wanted.  It can be common that an unresolved item can give us lots of added stress and eventually it is likely that it will come out in a way that you did not intend for it to.  This is why many would say it is a good idea to go ahead and talk about it to see where you are on this topic.

It is important to realize that the outcome may or may not be as you wish, and we will want to be sure that we go into the potential discussion with an open mind and be able to listen to understand instead of a specific goal to get the other person to see it our way.    The way to find out if your roommate is wanting something specific from you is to ask directly.   You seem to know them well and have a well established relationship.  You likely have more insight into how to approach them than you've given yourself credit for.

Of course, each person has the right to choose what is good for the, whether religion or otherwise.  They could very well be concerned for your well-being if they perceive that your actions are putting you in danger.  At the same time, it is your decision as far as who you spend time with and so on.  

I would estimate that not discussing this would lead to more stress and it would likely feel better to know the status for sure and have a defined direction.  This is why many would find it helpful to go ahead and have the discussion and know the status before going on break. Then you can enjoy break and not spend time wondering about it and second guessing things.  I am sure you worked hard during college and would benefit from a true relaxing break without any extra distractions.  As best friends, I would hope that you can have a discussion in a civil way.

Don't forget your "I" statements and clarifying questions to aid you in the potential discussion.