This post has nothing to do with transgender so you can tune out if you wish; It's about my almost-27 year old son. Since he was five or six he's been very independent, stubborn, and willful, making lots of challenges for me and his mother (we're divorced). He's also bright, attractive, and has a wonderful personality... when he's not depressed and sour.

A couple of days ago he told me that his mother is going to stop paying the rent on his cheap apartment. He wasn't asking me to pick it up, as he knew I would not. Essentially what happened is that for at least the past year or two she's been paying the rent each month, saying "Okay, I'll do it again this time, but this is really the last time. You must get a job, you know you can. Just do it and hold on to it." Instead he played video games, watched TV, surfed the Web, smoked marijuana, hung out, or stayed in bed, depressed. So now, finally, he's really going to be cut loose. To sink or swim.

He and I don't yell or fight. We enjoy each other's company, I pay for a burger and a beer, and we talk. He easily acknowledges his part in all this. And now he feels that despite the fact that he has a couple of weeks to get a job he's planning to be homeless. He told me that he thinks this will finally teach him the value of money, his things, and so forth.

Oh sure, we talked about all the downsides of being homeless. He did it once before about ten years ago for a couple of weeks. But after a lot of talk and his (to me) rather strange confidence in this plan, I told him it's his decision. I told him how much I worry about him, getting robbed/beat-up/murdered, sick, thrown in jail, etc. Also, I worry about me: that I just know that within a month or two he will call and say that he just has to have $50. Or that he's in jail and needs bail. And I will have to say no.

My mother (yes, the one who committed suicide) is the one who taught me, "Sometimes the most loving thing to say is No" and I think she was quite right. I told my son this, too, and he agreed that I should tell him no. And he also said that he's pretty sure that in fact he will still probably call to ask for the cash. And he knows I'll say no.

Jeez, it's taken so long for us to get to this juncture. I started saying no to him and his mom after the 3rd or 4th attempt at college: "This time really, I'm committed, I'll do it!" A couple of years ago I offered him this: if he pays for his classes and books, I will reimburse him as follows: for an A he would receive 100%; a B gets 75%, and a C is worth 50%. Anything less is zero. He's tried to do that a couple of times; I paid 100% for a pottery class once. I don't care what classes he takes. Just learn something.

He also assured me yesterday that no matter what he has no plans or thoughts about suicide. He will figure something out. I sure hope so.

Tough love. It is tough to love. By the way, this has all been reviewed with a variety of therapists and counselors over the years. I'm sure I could have done a better job back when he was a child. My wife says no, but I am sure of it. But I really did do the best I could.

Emma