Boomers are faced with many vexing questions—where to live, how to downsize, what medical plan to choose—but I will tell you in advance the one that's going to keep you awake at night: Should I attend my 50th high school reunion?

High school formed us socially. Or maybe deformed us. Naturally, you're curious to see how everybody turned out. Are the popular girls still mean and beautiful? Are the jocks still thuggish and aggressive? Did anyone become fabulously successful? How will my own career and lifestyle hold up? Will I be the belle of the ball, with my amusing stories about the time I interviewed Sandra Day O'Connor and my current life in a Florida retirement community?

Needless to say, I decided not to go. It was just too risky. Too many bad things could happen. The first tipoff was the old classmates who contacted me, trying to round up attendees. One couldn't seem to place me and the other had me confused with a real loser. The clincher was when I saw the list of people coming. None of my four or five friends, the people I really hung out with, would be there. To add insult to injury, they were all in the "Lost/Can't locate" column.

Over the years and through the grapevine I've heard things about the people I went to high school with. As far as I know we had two outstanding success stories. One boy went on to become the attorney general of Nevada, and one girl, who would call me up at night and demand I give her the homework answers, calling me vile names involving sexual orientation if I didn't, had gone on to become one of the top models of the swinging '60s. (Boy, I'd love to see her again. I have a few choice comments to make to her face, comments I've been working on for 50 years.)

No, I was not in the right frame of mind for a 50th high school reunion. I would let sleeping dogs lie and achieve my own closure. Then, about two days after the reunion occurred, I got an email with all the pictures attached—more than 600 of them. Well, forget about closure. I dropped everything and spent the entire day obsessively going over them. Here's what I learned:

The girls (and in this context it is appropriate to refer to 68-year-old women as girls) fall into two categories: those who've have had work done and those who haven't. Those who've had look better. Much, much better. Twenty years younger. I'm not pushing for plastic surgery, but to look good in reunion photos, it's a miracle worker.

The big problem is the neck. The girls were painfully aware of this. You've never seen so much scarf wearing in your life, even to the dinner dance. The class beauty had this little fur thing wrapped strategically around her neck as she performed the Twist.

The boys all looked like they should be addressed as "Gramps." They say men age better than women. Well, not in my class. Hair disappeared, noses and ears enlarged, and the physique of youth was long gone.

The two or three men who could still be called handsome had one thing in common—a full head of hair. I hate to say it, but that's what makes the difference.

While there appeared a genuine cordiality among the attendees, I could see the old cliques reforming. The popular girls got to be popular again, and held court, particularly at the dinner dance. A few, three or four, still had some allure. But most had turned into nice old ladies. In many cases the less popular girls had surpassed their betters as time went by and now had the edge.

I looked for signs of dissipation in the eyes of several of the big drinkers from the old days, but they have apparently cleaned up their act. In only two out of 600-plus pictures did any of the boys and girls look drunk. (Then again, maybe they didn't post the drunk pictures.) One person appears to have been in a horrible accident, but of course I'll never get to hear that story.

Everybody had to do the Stroll at the dinner dance, which I found a little odd as I could not remember a single party where that dance had been performed. For a minute I was back in high school: "They're having Stroll parties and not inviting me!"

The dead were surprisingly present. In fact, they got more picture time than I did. They had a tree planting ceremony to honor the two boys who were killed in Vietnam—better late than never, plus a reminder of what an intense period that was. Out of a class of 100, two were killed in Vietnam.

And at the dinner dance, a table was set up in the ballroom with the graduation pictures of everyone who had passed away. This was the most shocking image of all. There they were, so young and attractive, in their pearls and tuxedos, each with a votive candle in front, looking out toward a bunch of old people doing the Stroll. I was a little shaken to find out that both the girls I "dated" in high school were among them.

But wait. It gets worse. Somebody died. The very next day. She got home from her 50th high school reunion, went to bed, and the next morning her heart stopped.

Well, by this time I seem to have pretty much destroyed the high school reunion business. Should you go? If you were popular and still have your looks, definitely. If you were popular but lost your looks, stay home. If you were a nerd who made millions, absolutely, particularly if you have a trophy wife. If you were medium popular and had a middling career, I'd sit it out. Why rub salt in old wounds?

And if you're dead, don't worry. You're going to be there anyway.

This month I answer that burning question: Should you go to your 50th high school reunion?

For more from Bob Plunket, click here to read his Real Estate Junkie blog. >>

This article appears in the January 2014 issue of Sarasota Magazine. Like what you read? Click here to subscribe. >>