The date on the back of this one is missing so your guess is as good as mine.
I’m on one of those horse rides, and it looks to be in a gift shop. It could have been Virginia Beach, which would place this picture during my briefly unemployed period in Summer 1999. But based on hair lenght and my weight, it could be Ocean City a few years earlier. If I was a smoker, I could probably date it based on the price of a pack of Camels.
Only one: I really miss higher waisted pants/shorts.