How to Approach a Woman at the Grocery Store

Start with a short question or comment about something in front of you both: the strawberries, the cheese, a product you can't choose between. Keep it to a sentence, stand to her side, and let her answer or not. If she answers and stays warm, talk for a minute. If she gives one-word replies, say "thanks, have a good one" and go back to shopping.

It's a gamble, and the people who write about it say so. In the Ask Evie advice column on Substack, the writer says: "Some women find it flattering when a man strikes up a conversation in the line at the grocery store. Others find it creepy." The rule given is to only do it "in a populated place where a woman feels safe to ignore you."

In a Hacker News comment, the writer says there's "nothing wrong with saying hi and having casual conversation with someone in the grocery store." The same comment says that what backfires is being "leery or crude" or asking for a date right away.

Both agree on the same thing: be friendly, be brief and don't expect it to work every time.

The store has good moments and bad ones.

Good moments

• She's browsing, not rushing.
• You're both in a spot where people stop and look: produce, the bakery, the cheese or wine section, a sample table.
• The aisle has other people in it.
• She glances up or makes eye contact.

Skip it

• She has earbuds in. The Ask Evie column's realistic version of the story ends with a woman who "doesn't take out her AirPods" and walks away.
• She's on the phone, has a toddler in the cart or is clearly rushing before closing.
• You're at the checkout and she can't leave. In our view, don't start a conversation with someone who can't walk away.
• The store is nearly empty. The column's rule above says the place should feel safe for her to ignore you.

Don't come from behind her. Walk up from the side, where she can see you before you speak. Keep a comfortable distance. Don't reach past her, and keep your cart out of her way.

The best opener is a real question about what's in front of you. The same column says you'll have "a much higher chance of succeeding" if you talk about something you have in common. The example given: a man in the ice cream aisle notices a woman's concert t-shirt from his favorite band and comments on her ice cream choice.

Here are lines you can use as they are:

• "Random question. Are those strawberries actually worth it, or are they all hype?"
• "Sorry to bother you. You look like you know cheese. I'm standing here with three kinds and no idea. Which one would you pick?"
• "Have you tried this one? I can't tell if it's good or just well packaged."
• (to a woman at the sample table) "Is it as good as it smells?"

Each one is about the store, not about her. That's what makes it easy for her to answer.

Don't open with "You're pretty, can I get your number?" That column says leading with a compliment and a request for a number is less likely to work than finding common ground.

If she answers, ask one follow-up and share one thing about you:

You: "Random question. Are those strawberries actually worth it, or are they all hype?" Her: "They're pretty good. I got them last week." You: "Good. I'm usually terrible at picking. Do you have a go-to for this kind of thing, or do you just trust the label?"

If she's chatty, you'll feel it: she turns toward you, asks a question back, doesn't look away. If she's not, you'll feel that too.

If it's going well after a minute or two, say it plainly:

"I've got to finish shopping, but I've enjoyed talking to you. Here's my number if you'd like to continue this. If not, no worries."

Offer your number rather than asking for hers. A woman in an Upworthy list of tips from women says she prefers it: "I do prefer the offer of him giving me his number vs him asking for mine." It leaves the next step with her.

If she's polite but flat, say: "Good talking to you. Have a good one." Then walk away at a normal pace. Don't circle back to the same aisle, and don't trail her through the store.

Take it as information and keep your face relaxed. Don't ask why. Don't say "I was just being nice." Don't linger. She told you with her answer.

The column's broader advice is not to rely on chance encounters like the grocery store. She suggests meeting people through shared activities such as a faith community, volunteering or saying yes to social invitations. The Hacker News comment says that talking to strangers is a great way to get over shyness, and that the writer met a number of girlfriends this way. Treat the store as practice at saying hello, and give yourself more than one place to meet women.