n that note I am going to keep working with this individual and maybe he could eventually be happy
Are you looking for a loving relationship or to be someone's savior?
If I have a partner who I love and respect and is struggling, I'll do everything I can to work with him and help him to be happy. But to enter into a relationship with someone who needs to be "worked with" and who isn't happy in and of himself?
I'd run the other direction.