Update: Saved by a more generous spirit than I might have been!  Got an email today from the gentlemen in question: short, friendly.  I will reply & work some type of apology into my answer.   So Kudos to W for being nice (and bonus points for taking a hyphen to share a name with his wife!).

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My 20th high school reunion is coming up this year and the organizers have set up this nifty site where you can post your stats (career, marital status, kids – seems a little mainstream to me, not to mention heteronormative, although they do have  “committed relationship” option which could I suppose work for gay couples outside of Mass.) and pictures, etc.

 Anyway, I was pleasantly surprised to see (because there was no word of him at the 10th reunion) a picture and info about a guy I briefly dated in high school.  He seems to be happy, have an interesting career (he added some explanatory comments) and has a family.

Here’s the background to the bleg.   I dated this guy briefly and broke up with him on senior prom night.  I should have broken up with him a few weeks before prom & given him the option to go with someone else, or I should have sucked it up and waited a few weeks after, if for no other reason than kindness, politeness, or something.  I quite simply never should have dated him, not because he was a jerk or anything, just that I did not have any real interest in him.  In other words, I behaved like a total asshole as there was no reason to break up with him on that particular evening, which holds undue significance in general American culture.

So, here’s the question – based on his current location (he’s abroad & doing work that while interesting is probably not highly paid), I’m guessing that it is highly unlikely he will actually come to the reunion even though he’s posted info so that people can contact him.  I’ve felt guilty about this for about 20 years – do I email him and apologize for something that I dearly hope he barely remembers, but may possibly still be bitter about to the extent he’s given any thought to it?  Or by apologizing do I come across as a bigger asshole by assuming that my need for forgiveness (or need to apologize and thus atone, regardless of what his reaction is) is important enough to contact someone I haven’t spoken to in 20 years?

Any advice (and suggested approaches) would be greatly appreciated!