Don't do the crime if you can't do the time.

In what manner are things awkward? Old Boy-Toy's wife is unaware, as are their mutual friends.

This guy thinks that it would be less awkward if his friends knew about this stuff? On what planet?

Ahhh 43? I bet he is feeling old and, well, middle-aged. (go figure) Wants to let them alllll know just what a hottie boy toy he was, back in the day (cue bruce springsteen)and instead of just saying it, needs some form of whiny justification for such a prick thing to do. or not. I could be totally wrong. :D

Hmmmm, if I read that correctly, he wants to tell their mutual friends but not his wife. Sure, that's going to go well, they won't act strangely around her at all.

It was 25 years ago. Man up and live with it. If the old affair and her husband aren't telling anyone, then leave well enough alone.

Especially if you're being a little economical with the truth about exactly when you met your wife and when the affair ended, which I must admit to being a bit suspicious about. But maybe I'm just cynical.

I don't think blabbing about it would make anyone feel better except the LW, and maybe not even him.

He wants to confess?? Go tell a priest, man, and then forget about telling anyone else. Seriously, does he want his life to be more miserable than it already is? He just wants the woman's husband to not hate him anymore, sounds like. How is telling everyone going to remedy that? Reminds me of the guy who went to confession, tells the priest "Forgive me Father, for I have sinned. I am married with 4 children, 7 grandchildren and one great-grandchild on the way. I had crazy monkey sex with 2 20-year-old hot coeds last night."
The priest was astonished. "Is this your first confession? I've never seen you hear before."
The guy says "Of course you haven't. I'm Jewish. I'm telling everybody!"

HERE not "hear". ack.

"The woman's still with her husband, who still hates me. My wife knows nothing about the affair, but we live in a small town and are starting to run into these two at parties. Should I reveal any of this to our mutual friends? It would make things less awkward when we're all together."

Um first, before blabbing about sex in a small town (really bad idea...) how about apologizing to the cuckolded man, assuming you never did when you were 18? And perhaps extending some real gesture (just saying sorry is actually pretty easy--try *doing* something too as sign of regret) to show him you regret what you did may make your encounters less awkward.

Telling everyone in your mutual circle you cuckolded him years ago, however, is highly UNLIKELY to make your encounters less awkward. In fact, he could take an even more severe dislike to you at that point, couldn't he?

I get the same vibe as Raj. Not only does he propose to lessen his guilt at others' expense, he seems actually to want to brag about his exploits. Otherwise, how could a sentient being imagine it's a good idea to advertise said exploits around his small town?

You may feel better temporarily because you get to dump all this guilt you have been feeling for years.

The problem is you are most likely going to stir up a hornets nest by dumping these bad feelings on others.

Your temporary relief will not last long as the chaos you create by unburdening yourself will swirl around you. Good luck.

He's going to feel better precisely because of the chaos (and notoriety: Look how cool I am!) he certainly already knows he'll be creating.

I know people who brag about their business or artistic or intellectual accomplishments. Maybe this is the only thing this guy has to brag about.

This happened when Reagan was in office and he's still haunted by it? He's afraid to tell his wife something that happened a quarter century ago? Grow a pair and get a life.

I doubt very much that the LW has any guilt after this many years. He's deluding himself to think that blabbing will lessen the awkward moments. He has it all figured out in theory, however, in practice, it just won't go the way he thinks it will. It's got "disaster" written all over it.

This relationship happened when he was single. It's not like he has to "confess" to anyone all sexual deeds done in his single days. What rule book is he reading??

This guy sounds like an aging, self-centered idiot approaching man-o-pause. Just look at his signing line: "Boy Toy"... geesh. Take a look in the mirror and get a slice of reality, Bub.

acid wash jeans - hehehe - I lost the ability to control my breath swallow mechanism and choked on my coffee - I'm still laughing. That's why I love you Amy.