Here's one for a good laugh.
We get invited to my wife's 20th HS reunion in a real small town in southern Indiana, very rural, cows, pigs, barns, farms the whole nine yards. Our background is that we both work and live in Indy, both have 4 year degrees, both of us are professionals, she's in HR, I'm in IT.
Her twin brother tells us the reunion is going to be in a barn or we both understood it was going to be in a barn. I wear a flannel shirt and jeans (normally I wear casual attire for the office, she normally does as well.) My wife looks great in anything but she's got on a very nice wool sweater and jeans.
We go to the barn thing, it's a pre-reunion of sorts, very casual and we fit right in, in fact it was very cold, I'm wearing an LL Bean barn coat so I'm comfy, we have a beer or two, there's a nice fire, etc. This goes on for a couple of hours.
Next everyone says, hey lets go to the "such and such bar". I ask my wife "what is that place?" She said, "oh my, that's a really nasty hole in wall downtown." We didn't realize it but everyone else changes into dress clothes while her and I go as is.
We show up at "the bar" that's actually a place that was once a crummy bar that was completely redone and made into a really nice ballroom and was built for event rentals like wedding receptions, etc. So everyone else is dressed up in dress clothes, I didn't even BRING dress clothes and I'm sporting a freaking flannel shirt and jeans, she at least could pull it off, I look like captain hill jack!
So the whole time I'm being asked if I'm a lumberjack and getting cracked on by the locals. After my verbal a$$ kicking I found a table for us as far away as possible. But it gets better. While she is getting hit on by an ex-boyfriend who is short, drunk and whining about his recent divorce, a nicely dressed woman asks if she and her husband (who I can't see) can join me at our table. I say sure no problem.
So next thing you know off she goes and up walks the husband. So I got stuck sitting next to a guy in an Earnhardt t-shirt and matching hat and dirty jeans. Turns out this guy is an ex-con and now a janitor at a high school or manufacturing plant (I forget which now) in Ohio. I swear I drank more beer that night than I ever have in my life and as God is my witness I couldn't even get drunk, I felt painfully sober the entire evening.