A.

You have a wonderful rule not to hit on people while they’re working.

This other person might have a rule not to hit on customers. Great!

Both rules are understandable. But they get in the way of possible romance – or even friendship. 

Let’s start with friendship. Can you tell this person you’d like to take them out to honor all the work they’ve done for the community? Can you invite them to a dinner at your house where there’d be a few local friends?

If it’s a food or beverage store, you could say, “I’m using the ingredients I bought here. Come join a few people at my house to see what I did with them!”

If it’s a car shop, I have no ideas. But you get what I mean.

The gateway to a date can be a low-stakes friend thing. The goal is to get the relationship out of the store. It’s like having a crush on someone at a shared workplace. Things are easier to figure out once you’re at a restaurant down the street from the office.

Even if you get a no, you’ll know you tried – and they can always followup with their own request.

It might help to frame this in your brain as an attempt at friendship – because you might decide that’s all it is. You’re in the fact-finding stage of a new relationship. Save your nerves about romance for later.

– Meredith

Readers? We’ve had a bunch of “how do I ask this person out in an awkward place” questions. How has this worked for you? How would you want to be approached?

Send your own letter here – or to [email protected]. I’m reading. And again, I’m looking for questions about friendship complications, too.