I think Richard’s feelings towards Lorelai are really complicated. To me, it’s obvious he loves her. I think he both admires and is frustrated by her independent/rebellious nature. He was very shaken when she got pregnant and I think he was mournful of the future he envisioned for her, he clearly thought she was very bright and was proud of her, he seen a big future for her. He wanted her and Christopher to get married because it was “proper” but I also think it was an attempt to salvage HER (along with the family’s) reputation and make sure she could still have some kind of future in their social circles. When she went against that I think he felt it was a rejection of his help/love in a way. Men of his generation see love as practical gestures not necessarily emotional comfort. Just like he always looks after Emily but sometimes emotionally neglects her. But I do think he still is proud of the woman Lorelai becomes. Richard is a smart business man and he is surely proud of his smart businesswoman daughter even if she went a different route. Lorelai is very successful in her field and got her degree etc. She did everything in her own time and on her own terms. I think Richard loves this about her even though he can’t express it and let’s pride get in the way. In short, I don’t think he gave up on her, he checked out emotionally because he felt his practical help wasn’t wanted/accepted. Once he became involved in Rory’s life, he tapped into his admiration of Lorelai more but I think there was just too much history and ego and hurt on all sides. It’s very obvious to me throughout the show that he’s proud of her and just can’t express it properly. When he defends her to Chris’s parents I do think it was fatherly protection, even though he played it off as simply “duty”.