"but when we get into these convo's he is always reaching to hear this stuff... like he needs reassurances."


Does he specifically ask you for reassurances?

If he does not come out and say "I want reassurances", then he is not asking.

If he does not explicitly say those words, then its all in your head, and you're just twisting it up because its YOU WANTING him to be needing it. Its then about your need to say it, not his need to hear it.

i'd guess that your wrong assumptions to what he's not asking led to the demise of your R. stop doing it.

"In a ham and eggs breakfast, the hen is involved, but the pig is committed".