communicating

I've always been grateful for the ease at which Mr. R and I have been able to communicate throughout our relationship.  In my adolescence I was very much a people pleaser and my opinions and thoughts were swayed easily by those around me.  It took one significant relationship in my life for me to learn to form my own opinions and not to be afraid to express it.  Although this relationship ended in a terrible heart break at the time I will forever believe that the relationship was significant in my life because I learned my own voice.  Which I am so grateful for.  I've also learned once you have your own voice you must learn when to express it and when it's just not worth it.
Well in the last week I've been put in a horrible situation, twice, where I've had a really hard time communicating my feelings.  It's so frustrating because the topic we are communicating lies very close to my heart and I feel like the person I'm talking to isn't even listening.  I feel like he already knows what he's going to say to me before I've said one word.  He's inconsiderate and interrupts me when I'm sharing my concerns.  He doubts my judgement when I believe in this particular situation my judgement should be honored.  I don't know how to deal with it.  It's not just about getting what you want but feeling like someone at least respects you and understands the needs.

How do you deal with these types of people in your life?
I know that we are surrounded by people who communicate in different ways.
Do I just back on a wait it out? or continue to try to work with this person?

(right now it feels like the more I try the worse it gets)
I should say that this is nothing between me and a family member all is good at home :)