When is it *not* okay to ask a girl out?

Sounds like kind of a retarded question, I know. I'm just curious what people's opinions are.

There's one girl I know at church, talked a good # of hours. I got a thing for her but I'm not crazy over her. She's really shy too, so, don't wanna just be like "hey wanna go out," one day outta nowhere. Or would that be alright, to those of you who are really shy with people?
I've always asked a girl out within like a month or 2 of knowing em, never got any bad reactions. It's worked, too, number o times. Never dated a shy girl though.

Bonus question: (I think I know the answer to this one lmao.) How weird would it be to get asked out after talking a bit with a guy while you're working, whether that be at a grocery store, fast food, or a professional setting?
Had a great convo with a girl at a store awhile ago who I thought was cute. Not considering asking her out, being that I like another girl who I actually do know. But it got me curious what her reaction woulda been if I did.

I'm thinking that's a hard no, even if you think the chemistry is there but I dont know man. If a girl I thought was neat but didn't really know asked me out I'd be like why not, but I'm a guy.
When is it *not* okay to ask a girl out?
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