I feel sorry for the person who told the story, but I also feel sorry for him for the reasons you wrote. He probably thought he was doing something really romantic and awesome, and then it failed and he might not understand why.

I saw a post on Reddit a while back where I felt really sorry for the guy telling the story. He was so infatuated with this woman and tried everything he could to make her like him. I obviously felt sorry for the woman too. She even put a restrainingorder on him and rightfully so, but at the same time I felt so sorry for the guy, because he just didn't get it! He couldn't see how creepy his behavour was, and I wonder if this might have been one of those "nice guys", who thinks they're really nice to women, but they can't see that they're selfish and manipulative. I'm not defending his actions, the woman in question did the right thing, but I still feel sorry for him, because he can't see that he's acting in ways that negatively affects the woman he claimed to love.

A positive anecdote that is sort of related to my point in my other post: A date gave me vegemite once, because he's Australian and I had told him that I like Australia but had never tasted vegemite before. Out of context it would have been a weird gift, but with that context I thought it was a nice one (Even though it tasted awful).