I’m nopt sure mine fits with the tone of the thread, but mine came when I had a sex dream about a co-worker and, in the dream, I said, “No, thanks.”
I’d had my share of “headaches” up to that time, but in a dream!?! WT… H, I guess.
-When I noticed I was older than the Playboy centerfold
-When I met someone who had never seen B/W TV in a household setting
-When I met someone who had no idea what I was talking about when I described that plastic adapter you snap into the center of a 45 so you can play it on a turntable
I was in a bike shop last year and took one out for a test ride. While taking the bike outside I asked the girl how you changed gear on it - I knew that the shifters had developed since I’d last got a new bike in 1984. She misunderstood me and started to explain how derailleur gears work - to her the bit that was invented 90 odd years ago was the same as the bit that was invented 3 years ago.
It’s hard to explain why, but she managed to make me feel both old and stupid.
When a friend of mine asked me if I knew Phil Collins was in a band before he went solo.
It could be worse; I had a co-worker who didn’t even realize Phil was ever a “regular” pop singer. She thought he was just a “composer and singer of Disney soundtracks.”
When the ‘cover bands’ that occasionally play in a park near where I live stopped playing ‘oldies doo-wop’ and switched instead to ‘Billy Joel’… :eek:
Oh, while we’re on the subject of music: a few years ago, there was a local radio station that used to do “Now and Then” music blocks, meaning they’d play an new and then an old song by a particular artist. At any rate, I turned them on one day in the middle of U2’s “Mysterious Ways.” Far from my favorite U2 song, but I stuck around to see if maybe they were going to play “I Will Follow” or “Gloria,” or maybe at least “New Year’s Day” next.
At the end of the song, I realized that"Mysterious Ways" had been the “then” track. 
So, to sum up, you know you’re getting old when: a radio station plays a song recorded after you consider the artist to already have been washed up, and they call it an oldie but goodie.
Let me make you feel better, I think they were asking you because you just met all these guys tonight. They were being polite, not making you feel old.
As for me, I’m only 26, but I always feel old when I realize that the teenagers I have to supervise weren’t even born when The Simpsons debuted. That blows my mind in ways some of these other examples (which I can somewhat relate to) don’t.
…when you read in the Dope about the hot actress in the latest Harry Potter film (which you saw a couple days ago) and all you can remember is a child. You follow his link…and all you see is a child.
You know you’re old
When I realized I was older than the college football players–sorta felt old.
When I realized I’m older than the professional players–that’s old.
…when they talk about players who are well past retirement age and they are my age!
I dunno, man. If he’d been 23 instead of 33, the politeness probably would have taken the form of, “Dude, you want?” 
Ah, so old people don’t smoke pot. Excuse me while I inform a certain old pothead of that.
I didn’t say it was valid. But when I was in my early twenties, I would have felt it really dangerous to just assume a guy in his mid-thirties was “cool” like that.
Maybe it’s just because I don’t want to smoke pot that it makes sense to me. I was absolutely awestruck in my teens when my friend’s sister just lit up in front of a group of us without asking and thinking it was OK.
No one wanted to smell like that and we made her put it out immediately.
No, I get what you’re saying. I was joking.
I realized a few weeks ago that at work I casually refer to people 20 years old as “kids”.
I’m only 23
I started feeling a disconnect from “younger” people when I was in college. Around the time of the Bush 41 generation, ahead of the first Gulf War, it seemed to me like there was a big change in the culture. I was a child of the 80s .
I was at a boat party on the Thames a couple of weekends ago, and an attractive young lady asked if she could borrow my newspaper.
I thought “how nice, maybe she can help me with the crossword”.
Turns out she wanted a clean surface to hoover up some Colombian Marching Power from… :dubious:
Sigh… I’m only 29, and an ex-raver as well.
(Hah! That’s another one… admitting that I am an ex-raver. The thought of dancing in a field till 6am doesn’t sound half as appealing as an evening on a tuscan hillside with a bottle of wine or three.)
That was a cool essay. Subtract 20 years, and the Atari, there’s me.