I don't know if I've actually gotten worse as I get older, but at least I'm realizing more and more that I'm terrible at interpreting the body language of girls I'm interested in. It doesn't help that my "type" is the bubbly, smiley type of girl who's so friendly that guys mistake it for flirting all the time. There's this girl that I'm currently interested in, and some of the things she's been saying to me would be unmistakably flirting if she were a normal girl, but nope, I won't make that assumption because she's got that "accidental flirt" personality type. The only way to find out is to ask her out, but I'm also hesitant to do that because if she says no, I'll still be seeing her every day at work.
The bubbly flirty types are so hard to read, and if you call them on it most of the time they won't believe you anyways. But heck, ask her out anyways. So what if she says no? As long as you make the attempt relaxed and casual and she turns it down with some grace, then no harm no foul, and there's no reason for things to be awkward.