Dear Queenie,
I have developed a bit of a crush on a cashier at Cost U Less. I shop there regularly, and she is often working when I go. She is a beautiful Caribbean woman with a lovely laugh and one of those musical accents I could listen to all day. She's also exactly my physical type. I like women with some meat on their bones. Over time, we've developed a little routine. Nothing inappropriate. Just small talk while she's ringing up my groceries. A joke here. A comment there. She recognizes me now, and I always enjoy seeing her. I'd like to ask if she's single. The problem is that when I look at her and then look at myself, my confidence disappears. I'm an older white man. I'm short. I'm a little round. I'm divorced. And I only live on the island part of the year. Basically, I'm not exactly the gentleman from the cover of a romance novel. I also don't want to be that customer. She's at work. Being friendly is part of her job, and I don't want to mistake good customer service for romantic interest or make her uncomfortable somewhere she has to be. But I also keep thinking: what if I never ask and there actually could have been something? Queenie, should this short, round, older gentleman take his chance, or just buy his groceries and admire the cashier from afar? —Checking Her Out at Checkout
Dear Checking Her Out,
First, congratulations on possibly being the only person at Cost U Less paying more attention to the cashier than the total on the receipt. Now to your dilemma. You're focusing heavily on the wrong things. Short. Round. Older. White. None of these tells you whether this woman might find you attractive. People's tastes are wonderfully unpredictable. You like a woman with curves. Why are you assuming she couldn't like a man with some? The more important part of your letter is this: She's working. That changes how you should approach this. A cashier is required to interact with customers. She may laugh at your jokes because she genuinely enjoys you. She may also simply be very good at her job. You cannot safely interpret friendliness across a checkout counter as flirting. So don't. But that doesn't mean you can never express interest. The trick is to do it in a way that gives her complete control and requires nothing from her while she's working. I wouldn't begin with: "Are you single?" That's surprisingly personal when someone is effectively trapped behind a cash register. Instead, after one of your usual conversations, you could say something simple: "I enjoy talking with you. If you'd ever like to have a coffee when you're not working, I'd enjoy that." Then give her your number rather than asking for hers. And leave. No standing there waiting for an answer. No asking again next Saturday. No suddenly choosing her checkout line every time even when twelve other registers are empty. If she's interested, she has a way to contact you. If she doesn't, your next interaction should be exactly as pleasant and ordinary as the ones before it. That's what separates taking a respectful chance from making someone uncomfortable at work. There is one other thing you shouldn't hide. You live on the island only part of the year. If she does contact you, mention that early. She deserves to know whether she's potentially meeting someone who is available for a relationship or someone who disappears with the season. And stop rejecting yourself on her behalf. She is perfectly capable of deciding whether you're too old, too short, too round, too foreign, or exactly her cup of tea. Your responsibility is not to make that decision for her. It's simply to make sure that if you ask... she can comfortably say either yes or no. Now go buy your groceries. And for heaven's sake, don't suddenly start buying one item at a time just to go through her line.—Queenie
