A few come to mind..

1. Purchased a coffee from Artigiano in Vancouver, reputably the best coffee in the world, retails for around $100/lb. I think one serving was around $10-12 at this coffee shop. I guess I don't have a taste for fine coffee, if I didn't know how much it cost I wouldn't have thought any different

2. Had a $35 kobe beef burger at a fine restaurant. Easily the best burger I've ever had, but of course no where near 3x as good as a $12 burger. No regrets, this one was worth it just once

3. Watches, I've had a couple of impluse purchases.. figure I spent about $500 too much on one watch (I should have purchased the watch I originally had in mind), and another watch I paid about $1,200 too much as I didn't negotiate what I could have

4. Back in 1997 I recall spending around $600 on an 8MB Voodoo2 video card for my PC

5. In Hong Kong back in 2001, I ordered a $50 bowl of shark fin soup (trying to impress some girl hah). Nothing special here, I don't know what the fuss is

cheers,
elapsed