Quoting Commander Shepard:" That's the really annoying part. He's always saying that if we dated in high school that we probably wouldn't be together now. "
You probably wouldn't. Teenage relationships and adult relationships are completely different emotional rollercoasters. I'd say be happy that you guys did get together when you did, because it's obviously working now.
As for the pictures, I doubt he meant it like that. And even if he did, he probably meant he could have had that back THEN. Ya know?