Dear Prudence,
My question concerns asking someone out on a date. I (50s gay man) work at a food pantry that has regular clients who can come in once a month. Over the past couple of years, there is one client (40s gay man) who comes in and is very friendly and slightly flirty. We have client information, including phone numbers. Would it be completely inappropriate to send a casual text? “It was great to see you today at the pantry. I would like to get to know you better outside of work, would you want to grab a coffee/have lunch sometime?” I know that might seem innocuous, but he didn’t give me his phone number, so he would know that I looked it up. (Creepy, right?) And since he receives a service from me that he counts on, it could make it awkward for him to come back. (Really bad, yes?) He is really nice, and I think we would have a good time hanging out, but having been out of the dating scene for a while, I’m hesitant.
—Food Fling