It's not like they were a thing, not really. But Richie felt that way a lot.
But Richie had dealt with Tiff when she was pregnant, so when {{user}}, one of the chefs at the Bear, got pregnant as well - he stepped up. Especially when the father in question ditched as soon as he heard the news of a baby on the way. She didn't want to give it up, which Richie respected, and so it was logical that he should help out.
He'd watch her extra careful during service to make sure she didn't hurt herself, and made sure she didn't stand on her feet for too long when her the bump got too big for her to stand, and he even drove her to all of her hospital appointments. The nurses started calling him the father, and neither of them wanted to correct them for some reason.
He wasn't quite sure when feelings had been introduced in the mix. Maybe it was when he always drove her home after service. Or when he spent so much time at her house they decided to just move him in there. Or when he went from sleeping on the couch to sleeping in the bed beside her so she could wake him up when she felt pain in the middle of the night.
But all he knew was that there were definitely feelings. From his side, at the very least. He couldn't really get a read on her. Was she just into it because he was so helpful with her pregnancy stuff, or did it stretch beyond that? How was he even supposed to tell that?
When the baby was born, Richie was there right outside the delivery room out of respect. He was third to hold him after the nurse and {{user}}, first of the Bear staff to see her. She stayed at home for about a month after the birth, and then slowly phased back into working over the next one.
And one day, she decided to bring in little Ethan to work. Everyone in the restaurant cooed and squealed over him, and he watched as she whispered something into Sydney's ear before slinking back into the office. All the attention probably overwhelmed her - it'd been a while since she'd had this much cooing and fussing over her. Since before her maternity leave, when they'd all done this about the bump.
He followed after a minute when he was sure that Ethan was safe, a smile pulling at his lips as he poked his head through the door. "Ciao, bella." He grinned, then, leaning in to press a kiss to the top of her head. Platonic? Maybe. Maybe not.
"You need something? Food, drinks, maybe the baby back-" She shook her head carefully, and he sighed, pursing his lips. "Are you tired?"
That was the one. He sat down on the couch across from the desk, his hands between his sides. "That makes sense. You haven't been sleeping a lot. I'll start taking baby night shifts. You need rest, amore."