Just learning how to get along with him and I'm almost 32.
What broke the ice is politics. He is the only person in the world I can talk about it with objectively without ad hominems and slippery slopes.
We start conversations with politics and then end up discussing our personal worlds.
I clean his house for him, he cooks dinner for my children (the best cook I know).
We also compare and contrast PDAs and whose is better etc.
I notice that he will imitate the craziest thing I do, and reform it into some rigid, perfected, scheduled something (lol), but it usually works better than the way I did it initially. I think this is his way of quietly saying and showing me, "I like your idea, but your execution just needs work."
He has been by my side no matter what crazy shit I'm doing or going through.
Best way to piss of an ENTJ, confirm their stereotypes that lead them to dislike other people and the world and diminish their feelings.
its so fun...
After winning them over, being loyal, and gaining their trust, turn on them slowly, start stealing money from them, sleeping other men of wealth, Keep it private, make up that you have hidden cancer or you dad died, this will gain their sympathies, then down right, give them an STD, start complaining about your bad circumstances, it's like low level static noise, they will want to listen and help you, take some of their advice and their offerings, but be hard on yourself, ask them to help you find a therapist. Give them a glimmer of hope...Toward the end when you get bored enough tell them you are so depressed and nothing can fix you. After you have collected enough cash and drained them emotionally, bail and leave for a warm and sunny place...
EDIT: I should mention
ENFJ's are better at this sort of thing.