Dating Over 40: I Can’t think of What to Say

Last night the group coaching call was really powerful.  Jean asked a great question about starting conversations. Her friend suggested that when she sees a man who interests her, she should find a way to say something.

She was at the doctor’s office and a nice looking guy sat down next to her in the waiting room. Jean made herself put her book down, to think of something to say.  But no ideas came.  He was sitting right there, putting on his shoes and socks (not sure why they had come off but that’s probably another story.) Yet her mind was a blank screen.  Finally, she was called for her appointment and the moment passed her by.

Jean complains that she freezes like a deer in the headlights and absolutely nothing comes to mind!  She just doesn’t know what to do!

For starters, I think Jean should just make it a practice to talk to men.  Any time, any where.  Don’t wait until you see a man who pops your cork – that’s way too much pressure!  Instead, talk to any guy with whom you come into close proximity.  As an example, Jean could have said to Mr. Barefoot, "Do you think sock, sock, shoe, shoe works best, or one sock, one shoe?"  This meaningless type of question is just a conversation starter without much substance. But hey, that’ s all it takes.

Another thing for Jean to think about is where she’ll find men to talk to.  Her immediate reaction when I asked this questions was that she doesn’t really run into many guys. So I asked if she knows everyone in the building where she works – she said "No." What about in the elevator, in the parking lot, in the lunch room? "OK" Jean said, "I’m starting to get the picture."

See, men are quite literally every where.  It’s actually hard to avoid them unless you’re in a convent.  And the best places to strike up harmless conversation without pressure are all the mundane places to which life brings you. In line at the bank, grocery store, deli counter, or dry cleaners.  At toll booths, in the gas station or convenience store.  Honestly, opportunities abound.

You don’t need to marry these guys or even give them your phone number. But talking to them does give you an advantage – the edge of being comfortable striking up conversations, meeting new people, and flirting with men any time and any where.  That’s quite a skill and a big boost to your confidence.

And the best news? When you do encounter that special man, you’ll be so well practiced that he’ll just be another guy to you.  No freezing, just a smile and plenty of confident charm – ahhhh you’re relaxed and having fun!

Jean and I discussed how many times a week she thought that she should talk to strangers and she signed on for twice a week.  A bit lame if you ask me.  So I had her stretch that goal a bit. I asked her how it would be if she did it four times a week?  She cringed, but did agree that she’d get a lot more comfortable, a whole lot faster.

Lastly, here’s the biggest benefit of all.  Jean would have to start looking around her for potential men to talk to.  Now this would be novel because Jean spends most of her time totally focused on handling her tasks as quickly as possible to get home to her kids.  So as mentioned earlier in this piece – she doesn’t even notice any men around her!  With this homework assignment, she’ll have to start looking for men – and that is huge!  Now she’ll be looking for men and opportunities, a whole new mindset that changes everything.

It’s Monday.  Why not join Jean and try it yourself this week.  Talk to three or four men you don’t know.  Smile, and start a few conversations.  See what happens and notice any changes.  After a few weeks, my bet is, you’ll be very pleasantly surprised when you look back and notice how much your perspective and outlook have changed and how much easier it is to start a conversation.


Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

1 thought on “Dating Over 40: I Can’t think of What to Say”

  1. I like this idea alot. BUT a little concerned because of the prospect of speaking to a weirdo.

    I do actually talk to many people at work (who by the way are men). I have no problem.

    In fact, for the first time in my life I actually converse regularly with someone I am attracted to. However he is not attracted to me.

    I think he prefers them wild or thin or young or both.


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