Photo 99 was from the college days. This was Matt and Steven in Steven's dorm room at Erskine. If the date on the picture is correct, it was April 20, 2002, which makes sense.
Here's #100... the last of the Random Photo game.
And since it's the last one, I'll go ahead and give the answer...
This was me and Ginger in the summer of 2007 out on the boat. I miss the boat.
But I miss Ginger even more!!