pfft who wants to acknowledge trauma?? so much better to keep that shit bottled right on down and pretend it isn't affecting your life in terrifying ways?? i mean it's good for human growth and all but messy characters are the best imho so....
while their childhoods are pretty different, he learned pretty early on that his parents love was 100% conditional upon him being exactly who they wanted him to be and for a long time he had to tow that line in order to have a relationship with his younger brother whom his parents basically have always used against him which is oh so much fun. he hasn't had a serious adult relationship since his parents strong armed him into ending things with his (gasp) white girlfriend whose family sounds somewhat similar to naomi's adoptive family however a little more stability in that respect so i think he'd really get his and olenna's background to some extent, not that olenna has ever been all that open and depending on how open naomi is, he may just know the barest of bones of details about their fam. he's kind of a prickly pear when it comes to getting to know others and doesn't really care much if people don't like things about him, if anything he sort of leans into the things people find offputting about him whenever they're around in an attempt to keep himself from y'know, getting attached and ultimately losing someone again because surprise! he's a shell of a human!