I Want to Say Hi to Her. How Do I Keep the Conversation Going?

I have seen this woman several times at the grocery store. I can tell she is very shy. I am also shy and I don’t want to create an awkward situation for her.

I have made up my mind to say hi the next time I see her. Saying hi will be the easy part. She is very pretty, but I don’t want my first comment to be about her looks.

What do I say? How do I keep a conversation going? How do I make her feel comfortable when she appears so shy?

-Randy (Ohio)

Dear Randy,

I once had a man in a grocery store tell me I was attractive and would I go out with him, and I ran for the hills.

A woman goes out with a man not because the man is interested but because she is interested. So give her something to be interested in.

Focus on anything but each other. Talk about the weather, the produce, give her a tip about how to grill the meat she is buying or gossip about the strange cashier lady.

Any conversation will give you an opportunity to showcase yourself. And by talking about something external to the two of you, you will lessen the stress.

You can do this. Start a conversation.

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