Cary Tennis is Salon’s advice columnist. He used to be a hard-living music writer until he hit rock bottom. Unlike any other advice columnist I’ve ever read, his responses are interesting and deep enough that I enjoy reading them even when I can’t relate. Gawker regularly mocks his style as pretentious, but Jezebel says he’s the best advice columnist on the Internet.

In my 20s and confused:

If I were you, I might be a little angry that my culture neglected to tell me the truth about these things, that my education did not prepare me for adversity. I might be upset that I had not gained an understanding of economic forces, of class forces, of the way power is wielded in hidden ways in the workplace, how we are led to believe that things will be easy when they are actually hard.

My boyfriend is bad with money:

What cultural bias it is that makes his sort of financial immaturity less shameful than, say, sexual immaturity, or not being able to tie your shoes or comb your hair, or having a learning disability…Maybe it has something to do, too, with the knowledge a white male has that, any time he wants to, he can clean up his act and go out and earn more than you do. Maybe a certain privilege, built into the system, rewards him for, and insulates him from, his own irresponsibility.

I’m tired of graphic design. What next?:

You cannot change your life without encountering things you didn’t know about yourself. You cannot change your life while still believing that everything you think you know about yourself is true. Change involves shedding beliefs.

My boyfriend’s afraid he will cheat:

Because the consequences of marrying and divorcing are grave and complex, I suggest you talk about what would happen if he were to have sex with someone else. Would the marriage have to end right there and then? Or could you commit, now, to some sort of reconciliation process if that were to occur?

I’m an enabler at the end of my rope:

I know about metaphors. I know that symbolic behavior does not alter the world. But it does allow us to experience our own feelings. It allows us to graphically, viscerally experience what we are doing and how we feel.

Mom, lawyer, musician?:

As men we sometimes do not appreciate the burden of being constantly seen. To constantly be the object of others’ gaze. As if you were under surveillance! As the constant object, you must always prepare yourself for men’s eyes.

I studied print journalism: Now what?:

Paper itself is a kind of message; it tells us that information is permanent, whereas the Net tells us that information is in motion…If information is in motion, does that make it more or less true?…Obviously the world is in motion. So information must be in motion as well.

Should I leave L.A. after one year?:

You will suffer and hate everyone and then one day you will find yourself sitting at an immense console with knobs, and when you turn the knobs some people are thrown into the fire pit and others are elevated to the banquet hall, and you say, How did I get to be in this knob-turning situation? as if you didn’t, secretly, know.

He e-mailed us to say, “I’m dating both of you”:

He made you a nice dinner. He says nice things to you. Those things…are not the relationship. They are relationship-oriented products…As a man, I can tell you that sometimes when we want a woman to do something, we produce our best relationship-oriented products and present them to her as if they represented our current feelings toward her. But what they actually represent is how we think we might feel once we get what we want from her.

Let’s get Michael Jackson to tour the U.S.!:

I imagine that one’s particular attachment to Michael Jackson reflects, among other things, one’s troubled and contradictory relationship to Pan, who, incidentally, was also the god of theater. One thinks of Jackson and his animals and his purported interest in boys and children, and his genius for performance, and one thinks of Pan.