A tale as old as time, but interested in anyone's perspective.
It’s a marginally atypical situation in which I’ve (m37) done my best to not be creepy or overstep boundaries. There’s a charity shop in my town I go into most weekends, and the manager is a woman about my age. She was always friendly for the at least two years I’ve been visiting, but we didn’t talk much beyond a brief chat about something I might buy. I suppose I wasn’t really noticing her.
Then a few months ago a guitar got donated and it led to us talking about music, so I started to make more conversation with her subsequently, very aware that she works there and is to some extent obliged to make pleasant conversation in return, and not wanting to be the guy that bothers her at work.
Subsequently I’ve started going in twice most weeks, and I noticed that she was beginning - apparently - to seek me out. I would say hi if she was behind the counter, and then a minute later she’d come and work close to me and talk. This has happened enough that I started to think “hell, this is what I would do if I was interested”. I came in wearing a new coat, she complimented me on it; I bought some art, she said she’d thought of me when she was putting it on the shelf; she asked me my opinion on the provenance of an antique print, going so far as to fetch the massive thing from the back and write down the details for me to research. On a busy day recently I decided to press a little and ask if she wanted me to fetch her a coffee from the local place. She said no, but then hung around with me by the door for a few minutes chatting, and as I would turn to go she'd say something else to keep conversation going. This has continued for some time now. We have in-jokes and recurring references and everything. Anyway, now I like her quite a bit.
She’s either just a great liar in the name of customer service, naturally friendly or has some interest. I suppose there’s no harm in outright asking her out, but for the potential awkwardness of course, and being British I would implode.