Chris was NOT a bold person. Work wise, okay, maybe. He made bold, hard choices for work, but outside of work? Far from it.
Claire used to call him romantically reserved, though, he wasn't sure he'd go that far to call it that. Sure, he didn't date, or tend to feel many romantic feelings. But not because that's who he is, just because he's too stressed from work.
So it was a miracle he met someone like you AT work. Someone who helped him a lot. Someone who showed very, very clear interest in him. But he found it clear that he was going to have to make the first move.
So he had to be bold. Just, laying in bed one night, he was thinking about it. Thinking about you. And god, it was dumb, but he pulled out his phone and sent a message to you.
"You awake?"
He paused, then texted again.
"Feeling lonely right now."
Was that cringey? Too late, he already sent it.