Dating Over 40: Flirting Dilemma – How to Know When You’re Over Thinking

While this post is about a guy, this plan will work for women too. So jump in and try it! 

There’s this cute guy at the gym who I’ve been coaching a bit. There I am on the elliptical trainer, and he often comes up to chat. It often moves into a bit of a coaching session. Sam knows he’s got my attention – I can’t go any where for 30 minutes. And to be honest, I really appreciate the distraction from my workout –not my favorite thing.

Sam is 30, is in really good shape, a lean muscular body, 5’7" and a very handsome face. He’s friendly, sweet and personable. So what’s his problem? Well first off he’s on the shy side and a bit intimidated by good looking women. He could have more confidence and he’s completely rejection avoidance. Now that’s a real problem for a single guy who wants a girlfriend.
I’ve given him homework to imagine himself as the kind of guy who easily starts conversations with attractive women. Sam says that has helped a lot. He’s pushing himself to say hello and flirt a bit more than his usual hang-back ways.
Last week Sam told me about a woman he’s been watching. He thinks she might have a boyfriend and is concerned she might not be approachable because she’s always got her iPod ear plugs on. Sam asked me if I would check out her body language to see what I thought.
I turned to Sam and told him NO. Here’s how I coached him through this one:
"Sam, you are really over-thinking this and making up stories in your head. Maybe she just wants to listen to her favorite tunes while exercising. Who says she’s got ear plugs in so she doesn’t have to talk to anyone? If you want to talk to her, just walk up to her and say ‘Hi’.
Why are you already be creating rejection stories? Stop making excuses, take a chance and just go talk to her! Next time I see you (three to four days) I want to know that you have already had your first conversation."
Sam looked at me with an expression of surprise. He realized that what I said was true. Sam agreed that he makes up rejection stories in his head and he does this all the time. No wonder he has trouble approaching women! He sabotages himself by expecting to fail without ever talking to anyone. That’s a great method to stay safe AND stay single.
I recommended my original exercise, but added a new step. Not only did I want Sam to see himself as a guy who easily approaches and talks to attractive women, but I asked him to start imaging that it’s Labor Day weekend (three months from now). I want Sam to start look back on the most successful, flirty fun summer he has ever had. He thinks about all the great women he’s met and talked to and how much easier it got.
I’ll let you know how he does. But one thing I can promise Sam, and you too if you want to try this, is that if you really practice this vision, you will improve your confidence. This is a very powerful exercise that really works! It’s totally worth the effort and time invested so spend a minute or two a few times a day and watch how things change and open up over time. There just isn’t any down side so why not start right now?
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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