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

Dr. Wendy Walsh

Written by: Dr. Wendy Walsh

Dr. Wendy Walsh

Known as America's Relationship Expert, Dr. Wendy Walsh is an award-winning television journalist, radio host & podcaster, and the author of three books on relationships and thousands of print and digital articles. More than 1.5 million people follow her sage advice on social media. She holds a Ph.D. in Clinical Psychology and teaches in the Psychology Department at California State University Channel Islands and has been the host of "The Dr. Wendy Walsh Show" on iHeart Radio's KFI AM 640 since 2015. Walsh is also a former Emmy-nominated co-host of "The Doctors," as well as former host of the nationally syndicated show "EXTRA." She was named a Time Magazine Person of the Year in 2017 after speaking out about harassment at a major news network.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Reader Question:

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)

Dr. Wendy Walsh’s Answer:

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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