So, a while back I wrote this, and I think I missed one important point, that even though Jesus met and loved people where they are, he also never encouraged them to stay in their state of sin, or attachment.
Think about the story of the "Rich Young Man" from Luke's Gospel, when the young man asked Jesus what he needed to do to inherit eternal life, Jesus gives the simple minimum answer, follow the Law and Commandments. When the young man says he has, since his youth, Jesus calls him to more, to rid himself of his attachment to worldly things.
Similarly, in the story of the woman caught in adultery, after there is no one left to condemn her, Jesus doesn't tell her to stay in the same state of life, instead he tells her to go and sin no more.
So while yes, of course, Jesus meets and loves people where they are, he always encourages them to strive to be better and to live a morally upright life, and adhere to those strict moral teachings.
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