Dating OVer 40: Conversation Starters – How to Break the Ice with Men


In my 100 Day Challenge Group, one of the participants wanted to know how to strike up a conversation with a man she is interested in. I think the easiest thing is to pick up on something from what’s going on around you. But there are several other ways to "skin the cat" as the saying goes…(that is a gross saying isn’t it?)

Comments from the Environment
-This is one of my favorite songs. What do you think of the band? 
-Would you please help me get the bar tender’s attention?
-Have you tasted this appetizer? It’s really good.
-How do you know the hostess or host?
-Your dog is so cute – what kind of dog is it?

Personal Comments (You have to believe these or don’t say them)
-You have a great smile
-That color looks great on you
-What a nice shirt (touch it lightly on the arm for emphasis if you are really brave)

Comments from the World at Large
-How about those Mets, Nicks, Giants? (Depends on the sport in season)
-Local town news – did you hear about the board of education’s latest?
-Anything out of the news
-Beautiful day isn’t it?

Something Silly (If you are good at humor and feeling sassy)
-How did they ever let a man like you in here? (Then giggle of course)
-Why did your woman leave you standing here without her? (Good way to find out if he’s single)
-Do you have a woman at home who’d be jealous if I flirted with you? (ditto)

Clichés work! Don’t underestimate stating the obvious as a simple, but highly effective ice breaker. Most people are happy when someone else starts a conversation. Why? Because you’ve done them a big favor by making things easy. Trust me, this is something I really know not only as a dating coach, but as a woman who has tried it with great success.

#1 Rule
The number one rule for striking up a conversation is not to take your efforts too seriously. The first thing you say doesn’t really even matter. It’s not that important, so take the pressure off.

Just do it and get in this habit. You will have more fun, meet a lot of interesting people and have a few great stores to tell. I’m still doing this – you never know who you are going to meet or who that person might know. The more you do this, the easier it gets. After the first few times, you’ll relax and start to look for opportunities.

The more you look around for someone to talk to or meet, the more you expect to meet men, the more men you meet! It’s pretty simple really. What are you waiting for?


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.

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