Yeah, pleasing people. Unfortunately, the more you please some people, the more they take advantage! @Captain24
Being assertive doesn't mean you have to be rude.
And there are things we can be more assertive with than others. For example, I'm useless at being assertive when my niece wants to sleep with me... argh... hence she's still here!!!
Whatever it is, family seems to be huge for your family. Why I'm saying it is that I don't talk or see my parents more than once a year... yet you all hang out with each other, have each other for dinner, meet together. In a way, if you don't have this, you may miss it. I hear it can be challenging too. But that's with relationships in general. You can't have the joys without the pain... (and yes, some can be more painful than others).
As for the dogs, maybe they are just cheering you up using the only way they know how? Ruby knows when I'm angry at her. She puts her head down and goes to her pen. She's listens more now... but still absconds down the road. I'm yet to get a victory there. I think she's okay if there were no other humans, but when she sees other people in our court, she runs to them and they all pat her! That's the bad part. When I take her to the dog park, she stays by my side the whole time...