Is it a terrible idea to try dating a guy that works at our local supermarket? Everyone there knows my husband and me and we shop there daily, but gosh he’s so cute!!

You miss 100% of the shots you don’t take. Better an “oops” than a “what if.” I usually say go for it when it comes to cute guys, especially when there’s very little at stake.

Important note: don’t ever harass strangers. Regardless of gender, unwanted sexual advances can make people uncomfortable, and people in a service job often have to act nice even if they want to send you different signals. So do it in a self-aware, non-threatening way. Methods I’ve used:

  • Leaving my number on a receipt when my waiter was cute (with a big tip!)
  • Leaving my number on a leaf tucked under a cute hiker’s water bottle
  • Handing a cute bartender a coaster with my number saying “I’m sure you get girls giving you their numbers all the time, but anyway, here’s mine.”

You could try leaving him a cute note with your number - if there’s a tip jar, drop it in there with his name, or leave it on a receipt. Maybe something like “I’m so glad I’m in an open relationship, so I can give my number to cuties like you!” or whatever fits your voice.

Or, just walk up to him when he’s stocking a shelf or his cash register is slow, and be flirty and bold: say you’re in an open situation and you like him. If he seems confused or uncomfortable, drop it, but if he smiles and seems interested, leave him with a smile and your number.

Of course, if this is an issue of personal safety - if you live in the kind of community where this could blow up your reputation, or if you’re worried about the grocery store staff reacting negatively, maybe it’s better to drop it. But that’s your call to make. 

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