Evangelist - consider the "lawyer" of whom you provided an example. WHY did Jesus ask him what the law said?
Because that man was under the belief that the law was the way to salvation. Jesus didn't ask him what the law said to convict him of his sin; He brought his attention to the fact that the law couldn't save him.
That's not unusual, Jews naturally thought the Law saved them, or that they had kept it, Lawyer's aside. You'd be amiss in thinking He didn't use the law to convict him of sin, as He in fact did just that.
Note
Luke 10:25-37, how the lawyer asked who his neighbor is, the illustration of Christ to show how he had missed keeping it, and assuredly as 'the rest' (
Eph. 2:3) this man missed the mark. This is God's way, showing how we missed the mark and fall short, convicting of sin. Therefore he did not love the Lord with all his heart, mind, and strength, nor his neighbor as himself, which is possibly why he retorted with questioning who his neighbor is. So he had not kept the law and Christ used this fact to convict him of his 'missing the mark'.
As pointed out, the rich young ruler is a prime example that negated your first paragraph. He was an arrogant, prideful young man who sought Jesus. But even more so, in this example Jesus started with the commandments, but went beyond when He told the young man to give it all to the poor and follow Him; in other words, don't just follow the commandments, but exemplify the love He has for those less fortunate.
If that doesn't translate to "God loves you," I don't know what does.
The rich young man never kept the commandments, he fell short, as have all men;
Romans 3:9, 23. This was Jesus' point and why He stated for him to give up everything he had to follow Him, in other words the Christ of God was proving he had in fact
not kept the commandments from his youth up. The rich man was covetous, which is idolatry
Col. 3:5 and this showed he hadn't kept even the first of the commandments,
Exodus 20:3-5.