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

Dr. Wendy Walsh
Dr. Wendy Walsh Updated:
Discuss This! Discuss This!
Advertiser Disclosure

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.


No counseling or psychotherapy advice: The Site does not provide psychotherapy advice. The Site is intended only for use by consumers in search of general information of interest pertaining to problems people may face as individuals and in relationships and related topics. Content is not intended to replace or serve as substitute for professional consultation or service. Contained observations and opinions should not be misconstrued as specific counseling advice.

Advertiser Disclosure

DatingAdvice.com is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear across the site (including, for example, the order in which they appear). DatingAdvice.com does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers.

Our Editorial Review Policy

Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.