Each week in Dear Prudence Uncensored, Prudie discusses a tricky letter with fellow Slate writer (and her husband!) Joel Anderson, only for Slate Plus members. This week, they dig into “Food Fling.”
Dear Prudence,
My question concerns asking someone out on a date. I (50s gay man) work at a food pantry which has regular clients who can come in once a month. Over the last 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 text with a casual “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 would know that I looked it up (Creepy, right?). And since he receives a service from me which 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
Read Prudie’s original response to this letter.
Jenée Desmond-Harris: So I chose this one because I wanted to err on the side of making sure the letter writer didn’t sexually harass a client (particularly someone vulnerable and in need of food), but I’m worried I missed a creative way for him to make a move. As someone who’s always been a good flirt and has a knack for pickup lines, what do you think?
Joel Anderson: Hold up before I answer anything, I need to clear the air: You’re the one who once told me that you were a flirt, and you said it in a way that made clear it was an immutable fact about yourself, like having curly hair or long legs. Whereas I never remember saying this about myself, ever!
Jenée: Maybe I’m misremembering and you just said you never had trouble getting a date. Whatever! Do you have anything to add to help this man?
Joel: That’s also false but let me get down to business.
This is a terrible idea. I actually thought you chose this letter because of that time I was setting up landline phone service in Florida (yes, this was many, many years ago) and the customer service rep texted me back after the call to … I don’t really know what you’d call it. But she said she thought I sounded cute. And you know what I couldn’t help but think after initially being flattered? That it was wildly unprofessional and inappropriate.
Sir, please don’t do this. It seems like you have a good thing going for now. If things are going to turn personal, you should let the client be the one to make that happen.
Jenée: I’d forgotten about that customer service interaction. At least in that case, you never had to see her again and weren’t relying on her for anything after the call ended. It also reminds me of when I made a report about a stolen cell phone and the police officer who came to take it kept asking where I was going to hang out that weekend. Not great. I do wonder, though, if there’s some way that’s still within the bounds of professionalism that the letter writer can communicate warmth and openness. Like, I don’t know “Oh I see you got some apples this week! I make an amazing apple pie. If you want, I could bring some in for you to try next time I bake one.” What do you think? Too much??
Joel: Oooooh look at the flirt, back in action! But that’s pretty good.
I also think if the LW just lets the interactions continue, if they’re as friendly and flirty as he believes, that it’ll gradually escalate to a point where the client will eventually ask them out. But if the LW just doesn’t want to leave fate to chance, then yeah, maybe making it clear he’s doing something special for the client, like making an “amazing apple pie,” is a potential opening.
Jenée: I guess the rule I’m comfortable with is “You can be really, really nice and friendly to set the stage for him to make a move but you should stop short of suggesting spending time outside of the food pantry.” The closest I’d be comfortable with would be “Any fun plans this weekend? I’m going to the Memorial Day parade. Maybe I’ll see you there!”
Joel: No wonder you used to have so many suitors! But yes, the details of the invitation are much less important than what the LW shouldn’t do, which is make a direct ask or call or text them at their personal number. In fact, if the LW did the latter, they could find themselves being fired from their position.
Jenée: Nothing that would require the client to say “no.”
Joel: It’s definitely an open-ended invitation, like “I’m going to be here on this day” and then let them take it from there. Or per your earlier advice, the LW should do something that lets the client know he’s interested in him beyond their routine interactions at the food pantry. Even if it’s complimenting a special item of clothing, or turning “How was your weekend?” into a real opportunity for engagement and not polite small talk.
Jenée: Yep. Also: Do you ever wonder what could have been with the Comcast rep?
Joel: Not really, because I was in a relationship at the time! Do you wonder about what could’ve happened with the cop who wanted to help you with your phone?
Jenée: Not in the least. Imagine me as a Blue Lives Matter wife!
Joel: Well, you did once give money to a police fund but I’m glad we’re on the same page, lol.
Jenée: Okay that was a very different time and they got me with a story about injured officers. We’ll save the analysis for another column.
Joel: I can’t wait to read all about it.
