Crush question: should I or should I not offer to take him home...?

Jeez... so here goes. I like this guy I work with. Two problems: I'm older than he is and we work together. This guy is absolutely amazing. He flirts with me too. He's shy and admitted it to me and I'm shy as well. We like the same types of foods. He blushes when I'm around. I make him a bit more nervous because one time I was waiting on him to finish with a customer and he broke the ceiling tile he was talking about. He smiles at me and gives that "She's so cute" laugh. We text each other on different foods we like and offer each other suggestions...but we never quite make it passed there. When we walk through the store together he always breaks out and sings whatever song is playing over head...its so dorky but its adorable. I think he likes me but he never really initiates anything. I can't quite be sure if its the shyness or not. But I'd like him to. Two weeks ago, I was sitting across from him in the break room and he and our mutual guy friend/coworker were staring at me while I was looking down texting. When I looked back up I said, why are you both staring at me. They didn't say anything and my crush started blushing. I don't know what that means. ANyway, I know next week he gets off work super late like 11pm. I know he rides metro link (our subway system) home but thats sooo late. I want to offer him a ride home but I don't want to cross the line. I mean 8 months ago I asked him to take me home and he did. But we both got off at the same time. But its been so long and I know he's shy and I don't want be like I'm asking for attention... you know. Besides I get off at like 3 and I only live 10 minutes from work so it would be kinda weird for me to leave home and go get him to take him home. But I would do it in a heart beat. Would it be weird if I offer to take him him when he would know that I'd be coming from home to pick him up? Is that overstepping my friendship boundaries?