Dear 60-Year-Old Self,

You know that two-bedroom apartment you have in Florida, four blocks from the beach, for $750 a month? Take pictures: It’s a steal, and no one is ever going to believe you ever had it.

You should probably really ramp up your exercise program now. I mean the feeble effort you make at doing yoga, swimming, walking, and biking is all nice, but it’s really not enough. Especially when that walk just takes you and your pals right to the cheeseburger joint on the corner. Let me tell you, fitness is only going to get harder and harder every year.

And sure, right now you say you want to live to be 120, but you have a full-time job and no health serious problems. You haven’t even had a concussion yet from trying ice skate yet. But I’m getting ahead of myself.

I’m sorry I didn’t talk to you more seriously about saving for retirement, especially saving for sudden unexpected retirement, but wasn’t that birthday trip to Cuba a gas? I wouldn’t give it up for the world. Nor the trips to Europe, Costa Rica, or any place else you have in mind.

In fact, I think you should just go wild so when you are 65, and have to deal with some truly horrible external factors that are going to kick you right in the head, at least you can look back and say, “Wow,” I did have some fun. No money, but fun.

Granted, right now I am fighting off a black cloud of depression as I try to figure out how to survive through the next few decades with dignity and more fun, without money, a job, or security. Maybe you should write to your 50-year old self. Perhaps the big clue is there?

Dear 50-Year Old Self,

Whoa, just sitting here at age 60 thinking about how lucky I am, but what a waste the previous decade was, at least in terms of relationships. I do love Florida, although my love life is pretty well flat-lined, but maybe I could have made some better choices ten years ago, like not getting involved with that crazy alcoholic transvestite when I was living in the Ozarks. Yeah, that would have been smart.

So you there, 50-year-old self, take a note: You just got out of one co-dependent mess, relax and enjoy life for a while. There really is not anything wrong with about hanging out with your son and his best friend, sitting on the porch, and watching the world go by. I say, “Milk it as long as you can!” Just stay there in the woods by yourself and pay off some bills. Right? Why risk trying to “save” some poor damaged and deranged soul only to have him turn against you in the end, steal your pick-up truck, and threaten to kill you in the process?

By the way, this might be a good time to send a message to your 45-year-old self.

Dear 45-Year-Old Self,

Seriously, I understand that you are really tired of those cold winters in Maine, and you think it’s time for your good ol’ boy husband to pick up the slack, but before you pack up and follow him anywhere, I just want to remind you that you do have a job that you love and a very cool son, so what the hell? Why not just get rid of the husband and stay put? True, people say being single after 40 is a life sentence, and you are living in such a rural area that you likely never will find another date or another job again, and you are already working double-time at keeping everything together, but girlfriend, you have no idea what’s ahead of you in the Ozarks. I sure hope you have a Plan B should your husband do something crazy, like, oh I don’t know, abandon you and your son there with no friends, not family, and no job. Of course you have a Plan B, don’t you? By the way, how did you end up back in Maine anyway? I thought you left there for good in your 20s?

Oh, right. You are really not known for making great decisions now are you?

Dear 35-Year-Old Self,

Nebraska is not really all that bad now is it? You could learn to like football. Life there is steady, and being a single mom would be all right as long as you just don’t go and get married to some fool good ‘ol boy just because he makes you laugh or because his Mom is salt of the earth and the best grandmother you could ever hope to find for your boy. Oh, too late? Well, hang in there, and at least don’t invest in any real estate because the Farm Crisis is only just about to hit, and the Midwest hasn’t seen anything yet. Whatever you do, don’t believe that going back to Maine is going to be any better because there’s a Recession waiting for those folks, too. By the way, a lot of people live in urban areas and do just fine. Really, they do.

Letter to 25-Year-Old Self

Okay, getting out of Maine right now is a good idea for you, but I’m not at all convinced that heading to the hills of Arizona is your best choice, but it will get you away from all your crazy art school friends and drinking buddies. Of course, you did get accepted to B.U. to graduate school. What’s wrong with that idea? What about all that writing you want to do? Oh, I know? Biological clock. Tick tick tick. Well I can’t argue with that. Good luck. By the way, your future husband is a nice guy, but not a long-term investment. Don’t get too attached, to him or to Arizona. Take lots of pictures. Ektachrome keeps forever, and if you hold your Instamatic way out, you can get your own face in the frame.

Letter to 15-Year-Old Self

Stay away from those prep school boys. They are nothing but trouble. And those other boys, too. Stop goofing around in math class. You’re going to like math once you get to college and find out about Gambler’s Ruin and probability theory. Really! Whoda thunk it? And don’t believe Steve Aiello when he suggests that you need to dumb down to get a date. And definitely don’t believe Mr. Butler when he tells you these are the best years of your life. If they are, that explains a lot about teen-age depression.

Letter to 7-Year-Old Self

Ignore that art teacher who says your drawings are too unrealistic. Work harder on math. Read whatever you want. By the way, have those front teeth finally come in?

Letter to 4-year-Old Self

Do NOT try to hang from that rope on the swing set by your teeth. Bad idea.

Postscript: Sadly, my 4-year old self cannot read yet. Whole cycle is doomed to repeat itself.