To set the scene a little better, she has just moved into my area after graduating from college, so educated guess it's she's around my age, and when meeting up with her to see her dog that'd I'd be taking care of regularly, we had a nice conversation for an hour or so. Had some things in common, and overall I had a pretty good vibe about her, at the very least I think we probably could have been friends if we met organically (ie not as a business relationship). I personally don't need the money if things go sour and she no longer wants me to take care of her dog, and presumably it'd be easy enough for her to find a replacement, so I'm not too worried about that. Should I make an attempt to ask her out, either as a friendly event, or as a date? And if so, how should I go about doing it without it being creepy or something?
Should I ask out this girl, who's dogs I pet sit regularly?
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