I know someone who's my parents' age, (part of the baby boomer generation), has a kid who's in his 20s with no job, no college, and no plan of action, and she seems to be not pushing him at all. She sometimes wishes that he would do something and expresses her concern, but she never pushes or forces him to do anything. This makes me trust her. The fact that she's not pushing her kid to function and is letting him live at home without doing anything makes me trust her and feel like I can share stuff with her.
As much as I hate baby boomers on the Internet, some of the boomers I encounter IRL are really nice, and sometimes I feel a real bond with them. I have always gotten along well with adults until the whole millennial criticism started. But I have to keep in mind that people my parents' age will often have kids my age, and I can tell if they're trustworthy based on how they treat their kids. Seriously. If I think they're pushing their kids to be non millennial and be all hardworking and unentitled and all that, then I wouldn't trust them. But when I hear that they're not doing that and that they're doing stuff for their kids in their 20s and even 30s, then I know I can trust them. That's how I determine whether I can trust a boomer.