16 High School Reunions That That Didn’t Go Well

Five year reunion- one guy (always kind of a marginal figure in HS, but a nice person), after some sort of discussion, got his paycheck out and got loud saying “Now do you think I’m a loser?” “Don’t believe how much I make? Check this out” Of course, he just made things worse, and everyone was laughing at him. I mean – he had his paycheck on him? Haven’t seen him since, BTW.

At my 10-year reunion, the organizers were doing the thing where they give “awards” for the person who came the farthest to attend, the person with the most kids, etc. The award came up for who had the oldest kid, and people started shouting out their kids’ ages. When it quieted down, this shy girl near the front said in a normal voice, “11” and then we all realized why we had stopped seeing Heather right before graduation.

At my 10 year high school reunion, we had a decent turnout, maybe 100+ people. We were at a pretty nice hotel banquet hall.

There was one guy I had known all through high school, and he was a well known stoner. I’ll call him Chris for this story.

I see Chris walk in to the banquet hall, stop in his tracks, turn around in a very slow 360 degree circle, surveying the entire room. He just says, “Whoa…”, and he looks visibly alarmed.

He stops and his eyes settle on me. I say, “Hey, Chris! Long time no see, man!”. He kind of slides over to me and whispers in my ear, “This is really weird… I’m pretty sure I know every single person in this room.” And that is when I realize he is wearing the same clothes as all the banquet hall workers.


I walk him out to the front lobby, and explain it’s our 10 year high school reunion. He is mortified, beyond embarrassed. He was never contacted, and didn’t even realize it had been 10 years since we graduated. He just knew he was working another catering gig in a neverending series of catering gigs.

I make him take me to his manager. I explain what is happening and tell the manager there is NO WAY this guy is working his own high school reunion. Awesomely, the manager agrees. We find a different suit jacket and tie for him, and I take Chris back to the party. He ended up having a good night.

It’s been a decade since i finished school. I see an old classmate sometimes when he does maintenance work in my apartment block. About a year ago he asked if I was going to the reunion organised by some of our classmates. I said no because i couldn’t think of anything worse and also hadn’t been invited. (Apparently they organised it over Facebook which i dont have.)

When i next saw him 6 months later I asked how the reunion was and he exasperatedly explained that it had been a real s@#t show. The mean girls had started planning it together, fell out and then started each planning their own. So there was about 4 s#@tty tiny awkward parties and everyone was confused.

Small college reunion with my core group of friends from university. This was about 5 years after graduation. We all partied pretty hard in school, but mellowed out in our late twenties. Decided to all meet up for dinner at a local bar/restaurant. Think Applebees, but nicer.

One guy showed up already wasted, with a duffle bag full of multiple packets of weed and the bottle he started on before meeting us. He decided we were boring, finished his bottle in the restroom, and refused to come out. He ended up passing out there.

Bartender kicked him out. He came alone in an uber, and we had no idea where he lived. None of us wanted to take him to our places (he was angry, puking and belligerent), so we dropped him off at his last known address.

His parents’ house.

Both of them answered the door, and we handed him over. It was past midnight and incredibly awkward.

He’s not invited to the next reunion.

Not mine, but my mother went back to her 40 year reunion last summer. In December she left my father (36 years of marriage) for her high school sweetheart and is now living with him.

The people who were supposed to plan our high school reunion dropped the ball, so I figured it wouldn’t happen. But then this other dude from our high school stepped up to plan it. He was in a graduate program and also working part-time at a banquet hall, and he said that his boss would give us the banquet hall space for free. It was a really nice gesture, and he seemed really into it. He had been miserable in high school. Grumpy, sullen, unpleasant, mean to other people. He came out in college, so maybe the weight of having to keep it a secret was part of why he was so unpleasant. Maybe he’d be more fun now.

I was working a s@#t job and had no savings at the time, so I was neither interested in having my former classmates pity me nor was I gunning to shell out a lot of money to attend. Plus my s@#tty ex might be there and that didn’t feel worth it.

The organizer made a facebook event and asked people to venmo him the cost of admission prior to attending. He wanted something like $15-20 a head, I can’t remember. Anyway, it didn’t really feel with paying for. Maybe if there would be some drinks included or something, I would go for an hour.

I sent him a private message asking what the admissions ticket covered — food? Drinks? The space was free, after all. He posted publicly on the facebook page that if the cost of admission was too steep, “message me and we can work out some financial aid.” Uh, what? I then publicly posted, asking what the admission cost covered. No response.

Other people asked too. He said it would go towards having a bartender and server dedicated to the event space, as well as towards food. Okay, fair.

Folks, HE WAS THE SERVER. My friend showed up having not yet paid him, and he barred her entry. The people who had paid the admission cost showed up to an empty banquet hall, were given a menu by their former classmate, and told to order their own food and drink from him. He pocketed the admission ticket money as his fee. After an hour, he brought out one (1) grocery store sheet cake for 75 people to share. That was it.

It wasn’t really bad, just odd. A guy came with full Kiss-style make up on – white face, black shapes around his eyes and black lips. We were too awkward and polite to mention it, so everyone just chatted with him as though it was completely normal to turn up like that.

My 10 year reunion killed itself before it happened.

Turns out our class president (traditionally in charge of organizing) took a hard turn into a Footloose character after high school.

Highlights of her event planning include:

– No alcohol allowed, not even BYOB

– A few classmates in a reasonably successful band offered to play for free. She was adamant there would be no music or dancing

– Plus ones were to be spouses only. Two guys happily told her they’d bring their husbands, and she kicked them both from the Facebook page.

– The venue was the high school’s soccer field. In Iowa. In August. We were welcome to bring our own chairs.

– A few people offered to bring beanbags and bocce and similar games. She said no, because it would make the reunion “too much like tailgating”

– Suggested entertainment was a guided tour of the school, which had undergone zero change since we graduated.

– Catering was from Hy Vee, which is a grocery store. Their food is actually ok, but —

– Tickets were $60.

It was ultimately cancelled because out of our class of 300, less than 10 people bought tickets.

Didn’t happen to me, but I had this friend who got someone pregnant back in the day and she kept the kid, they’ve both been great about it, he helps financially but that was the extent of his contribution. She married soon out of highschool and met a great guy who has been the de facto dad.

Either way, it’s a day where you “bring your kids if you have them” event and someone let slip that my friend is that kids “real”dad. And the kid herd it and it was a f@#king s@#t show. Everyone was trying to figure out who said that, and how could someone spill that secret, etc.

In the end my friend pretended he was shocked, and laughed it off as a joke, which honestly i front of the kid was probably a good move.

One guy had made not one but two fortunes and had a net worth of well over $100 million by our twentieth reunion (high speed modem patents in the late 1980s, early investor in broadband. right place at the right time). He’d already retired. On our classmate update bulletin he listed his occupation as “unemployed and unemployable” as a bit of a gag. Some of the well-meaning but clueless types sought him out to offer encouragement and tips on how to find work.

Leave a Reply

Your email address will not be published. Required fields are marked *