You know, its possible that some motivation for his nudging is the recent loss of his wife. It's still completely unacceptable that he does it, but maybe it can sting a little less when he does if some portion of it is wanting you to have what he had.
Yeah. I know that his interfering comes from wanting us to be happy, rather than as a way of condemning our sinful ways. He just thinks he knows the One True Way to be happy, but it doesn't mesh with our happy. I know it's easy for me to say this as a non-parent, but -- parents gotta let their kids find their way (except maybe Charlie Manson's parents; they could have maybe gotten him into a youth orchestra or something), even when the kids' way doesn't line up with the parents' way.
I could easily just tell Tim's dad to fuck off if I thought he was being judgey, but while there's a little judgey there, it's mostly an issue of I Want You To Have This Good Thing AND I Know How You Can Get It. And that's harder to meet with profanity. I'm still not cool with it, I'm not budging on my boundaries, but knowing his motive makes it easier for me to let my anger cool off.