DRAMA! AskMeCha: need some dating help... →[More:]Anyone ever successfully asked out someone that provides them a paid service (not that kind of service lulz)?
Here's the situation: I have a bit of a crush on the woman who cuts my hair.
I've been going to her for a little over a year (essentially the whole time I've lived in this city). We've always had pretty easy conversation. She's read at least one book I've recommended (a finance/econ book, no less, which is my profession). She has a sardonic sense of humor very much like my own.
Through our conversation, I know that she's single and recently bought a condo in my neighborhood. She has mildly complained about bad luck on first dates and being alone of Valentine's Day.
I haven't notice any clear-cut signs that she's interested in me romantically. But my track record tends toward obliviousness and I don't know how demonstrative she is anyway.
Normally the awkwardness of the situation would scare me off entirely. But, to be honest, I've not made much of a social or romantic life for myself since I've moved here and I'm starting to get restless. Not that I'm only interested in this woman because I'm lonely; rather, I'm considering what is for me an "advance maneuver" in dating because I got to start somewhere and she's the most person I'm most interested in.
But how do I do this? I can't imagine sitting in her chair with a cape draped over me and asking her out while she cuts my hair. Not to mention all the other employees and customers within earshot.
Is this just a hopeless awkward scenario? Am I kidding myself about what she may or may not think about me?