It's always best, I think, to allow a person to participate in their own life lessons w/out interference ...
Seeking it out is different; they have directly asked for information ...
As for myself, I will approach a person I'm drawn to & start a conversation, most times, just by listening it helps her/him uncover w/the answers they hold inside ...
Remember, our answers are inside our own self ...
There will be times when what a person untangles w/in themself is not the same as what you & I feel or think they need to know about or how they should approach it ...
People will always believe their own personal interpretation of the truth & proceed from there ...