'Keep your crazy in, lady': 15+ awkward high school reunion encounters

Author image for Ben Weiss
Ben Weiss • Writer and Editor
Feb 8, 2024 2:00 PM EST

High school reunions almost never end well. If you managed to survive your own reunion unscathed, please feel free to share any advice on how you pulled that off in the comments. However, if you're like the rest of us and you were also silly enough to attend yours, you probably had at least one awkward encounter that still makes you cringe when you think about it. After all, high school reunions are one of those bizarre phenomena where old dynamics resurface almost immediately. You might end up reconnecting with an ex, a crush, a former friend, or a former enemy. You also might end up having to suffer through a conversation with someone whose name you cannot quite place. 

All of these types of awkward encounters and more were shared by these Redditors via the following r/AskReddit thread. Keep scrolling below for the full anecdotes. For more content like this, here are some funny stories where people watched their enemies make colossal mistakes.

Advertisement
  • 01
    r/AskReddit. Posted by u/DrMonkey7 What's the most awkward thing you've witnessed at a high school reunion?
    via Antenna
  • 02
    Gonzostewie. I play in a band. We got booked by a restaurant "for some class reunion". I show up to set up for the gig & it's my class. I wasn't even invited. 14.6k Share ...
    via u/DrMonkey7
  • 03
    Surullian At my 10th, the organizers gave "awards" to people for various reasons. One girl from our class was given an award for having the "most kids" of anyone there. She'd had 4 by different guys which was part of the announcement. The look on her face as she slinked up to the podium said it all. 6.8k Share
    via u/DrMonkey7
  • 04
    DrMonkey7 OP. My wife (at the time) and I had dated all through HS and college. We married and had a child. We still had a few close friends we graduated with that were going as well. I would say there was about a 70% turnout. We had a good time and everyone got pretty d. We all mingled and my wife talked to a guy who she had cheated on me with right after HS. They didn't speak for more that 3 minutes.
    via u/DrMonkey7
  • 05
    They hadn't spoke since that day almost 10 years before. We had moved passed it and had a family, at least that's what I thought. Less than a month after the reunion I could tell that something wasn't right, when I asked her about it she told me she wasn't happy and wanted a divorce. We had been together for a VERY long time and I was devastated. After a week of feeling like I had failed and doing everything I could to win her back I discovered she had been having an affair with that same guy. 6
    via u/DrMonkey7
  • 06
    [deleted] Haven't had a high school reunion yet, but here's a fun one from my Mom's third reunion. She went with my dad back to her hometown for the reunion. My dad grew up in a different place, so he didn't know anybody there. Bored out of his mind, he decided to have some fun and found a way to discreetly ask someone who the biggest juvenile deliquent, troublemaker was in their graduating class. Let's call him... Albert Davis. So, my dad went to the nametag table and found Albert Davis's namet
    via u/DrMonkey7
  • 07
    feralturtles . Someone made a speech along the lines of, "...to all of those that felt picked on or bullied, I have something to say to you." She then started to sing"Let it go" from Frozen. 4.8k Share
    via u/DrMonkey7
  • 08
    JustaReverseFridge. My friend said her cousin's high school reunion was really awkward because this guy ran up and kissed his high school girlfriend without her asking and then got in a fist fight with her husband, did not turn out well from what I hear. 2.2k ↓ Share
    via u/DrMonkey7
  • 09
    merkmill My mom's 35th high school reunion was at a bar that I frequent quite a bit... I walked in with my mom and went up to a bartender that I know to order a drink for my mom and I. He looked up at my mother and I and immediately got super shy and weird and then said, YOURE THE DAUGHTER OF (my mom's name)??? Apparently he had a huge crush on my mom in high school and my uncle beat the out of him because he creeped my mom out. Very awkward indeed. 2.2k Share
    via u/DrMonkey7
  • 10
    lorum_ipsum dolor. The captain of the football team was a pretty sad sight. He looked like and was so proud of sneaking booze in with his flask. I mean, it was a cash bar but the prices were reasonable... 2.1k Share
    via u/DrMonkey7
  • 11
    jacksake1. Not me but my BIL's highschool reunion. A guy that was severely bullied in highschool started a Facebook group to get the ball rolling on planning a highschool reunion, he planned the venue, food, drinks and asked everyone pay a ticket price to cover it all. He organised the money go into a provided bank account, received 200+ peoples HS reunion dollarydoos and to be heard of again. Never Ive never laughed so hard in my life. ↑ 1.9k ↓ Share
    via u/DrMonkey7
  • 12
    RubyWhiteArt. People coming up to me asking me what's up and seem to know a whole deal about me while I have no memory of who they are at all. 1.7k ↓ Share
    via u/DrMonkey7
  • 13
    honey579badger. When i was like 6 i went to my dad small town 30(?) yr reunion. His ex fiancé (not my mom) was dressed in her prom dress. And kept talking to me saying she should have been my mommy. Even then i knew that was weird. Keep your crazy in lady 1.4k Share
    via u/DrMonkey7
  • 14
    [deleted] At our 15th they asked, then gave out prizes for the person who'd traveled the farthest to attend, traveled the least far to attend, had the newest car, the oldest car, the youngest child ... The look on the MC's face when he realized what asking for the oldest child would mean... ↑ 1.2k ↓ Share
    via u/DrMonkey7
  • 15
    jobrody The lighting was dim, we were old, and some nitwit decided to let people scrawl their own name tags which then hung on lanyards at crotch level. Nobody could hear anything over the snot-nose DJ blasting "Eye of the Tiger" and trying to figure out who you were talking to was pretty awkward. ↑ 952 Share
    via u/DrMonkey7
  • 16
    jinxsays Got invited by Facebook message (we're not friends on fb) by one of the girls who made pretty much the whole time I was there a living . Didn't attend obviously, because everyone I wanted to keep in touch with I did - but got a "aw sorry we missed you hun, we should do lunch soon!" message. But, why? Selective memory, orrrrr? 689 Share
    via u/DrMonkey7
  • 17
    [deleted] Nothing. And by nothing, I mean the awkward feeling at being one of the twelve who showed up. 685 Share
    via u/DrMonkey7

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

high school karen entitled funny petty reunion students Reddit askreddit reddit thread
Scroll Down For The Next Article