Guys what does this type of behavior mean?

I kind of have a thing for one of my coworkers we always flirt but we've never taken it further then that

So one night me him and a few of his guy friends went out to the bar and having to take one of them home and being underage I didn't drink with them. After they'd had a couple rounds I guess they all felt bad for me so they offer to all go to his place and let me drink and all of us would spend the night so I wouldn't have to drive anyone home

Now that sounds normal, but I'd never hung out with him outside of work before and I had plans in the morning so I said I'd join them next time but not today everyone seemed fine with it except him, he started saying that I should let loose because that's exactly what I need and that I shouldn't let something I felt like I had to do get in the way of so thing I wanted to do and made me promise I'd join them next weekend

What does all this mean? Does he have real feeling for me or is he just trying to be a friend?
Guys what does this type of behavior mean?
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