<human>: So I [32M] am very inexperienced for my age, but I'm in a good place right now and I'm trying to get things together. I have a bit of an unfortunate pattern of waiting too long to ask women out, and yes, I've done it again.

At the same time, I have really given this woman a lot of attention. I invite her to do things with me (and she does them), I always chat with her whenever I see her, I often walk her to public transit after I see her, we text back and forth regularly, etc. I really enjoy her company, and I know she enjoys mine. The problem is, I don't know if she enjoys my company as her guy friend or if she would be interested in dating. If it's the latter, I want to give it a shot. If it's the former, I can live with that too, but it's important for me to know.

There are some unfortunate complications, here. First of all, I know her from dance class. Dancing is, by its nature, flirting. I've danced with her hundreds of times. I also have a lot of trouble separating flirting because flirting is fun and flirting because there's actually interest. I also have a sense that women I've developed feelings for in the past didn't expect it when I asked them out, and that made things a little awkward.

So with that in mind, is there anything I can do to get a woman thinking about me as a sexual being, and to make her realize that I'm interested in dating her *before* asking her out so that it doesn't come as a total surprise?

If it does come as a total surprise, does that make you uncomfortable or is it ok, but just weird?

Also, what can I do to keep things from being awkward (from her side) if she ends up saying no?

Give me the gist of the text in a nutshell
<bot>: I've waited too long to ask this woman out, but I still want to. What can I do to make it comfortable for her, whether or not she's interested?