Len really wasn't one to toss pity around. He didn't have time for that shit, especially considering his own personal background. So his reaction had less to do with feeling bad for Barry and more to do with that sudden overwhelming sense of disappointment. Which, to be fair, probably came from an entirely selfish place. But he'd never claimed to be anything else.
"You are broken though," he had to point out. Not to be patronizing but acknowledging it was kind of important. And he already had the feeling that skirting around the issue like a giant elephant in the room was going to win him no points. Not that he was fishing.
It was tempting to get down to Barry's level. Eye to eye, but he had a feeling that wouldn't go over well so he avoided the instinct. So he kept his face neutral and decided to plow straight ahead. It wasn't like say too much could make the conversation any more awkward than it already had the potential to be. A gentle hand he was not, but apparently Barry didn't need that anyway.
"Question is, are you broken here?" Len tapped the side of his head, because that was honestly important. Broken bodies could be mended. Broken minds not nearly so much. He knew that better than most, in fact.