Dating Over 40: I Meet Lots of Men But They Don’t Ask Me Out

Joanie has been working with me as her dating coach for several months. A good looking woman at 34, she easily attracts plenty of male attention. Sometimes they ask for her number. Yet, in Joanie’s session last week, she asked me what she could do next to keep the ball rolling with one of the men she liked most.  I took a step back and said, “What?”

Filling me in, she said it was obvious Jeffrey liked her, but his shy nature was keeping him from asking her out. That’s why she had invited him to a dinner party with friends and out to sing karaoke. This took me by surprise – I had no idea she was asking the guy out, a “no-no” in my dating handbook.

My take on Jeffrey was very different. I wasn’t so sure it was OBVIOUS he liked her. Usually, when a man likes a woman, he will pursue her. But Joanie herself had taken on that roll. In fact, she had been pursuing Jeffrey by asking him out – which at the beginning of dating is best done by the man for many reasons. In explaining why this is, Joanie could hear how she was sabotaging herself. After all, her invitations were not working to coax him into reciprocating and asking her out.

Jeffrey could interpret Joanie’s invites in two ways:
1. He might think she wants to be friends since she invited him to events with her other friends
2. He might think she’s being the aggressor by asking him out

Neither interpretation will likely work.  Joanie could be confusing this guy.

The truth is, Jeffrey knows exactly what needs to be done for Joanie to go out with him and if he were interested, or if Joanie gave him a chance, he would do it. However, her interference was getting in the way of discovering just how interested Jeffrey really is.

As a woman, you want to date a man who demonstrates his interest. A man who calls or emails, wants to  meet you, asks you out so he can get to know you and then repeats the entire process. When you jump in to get the ball rolling, you lose your ability to determine his true interest level. Just because a man says yes to your invitation, doesn’t mean he sees you as a romantic partner. The only way to gather data about a man is to observe. If you take an active roll, you eliminate your ability to do this.

As Joanie’s dating coach, I recommended that she stop asking Jeffrey out and inviting him to things, as well as any other men who she feels attracted to. By not initiating and using her feminine energy instead, Joanie will stop wasting time on men who don’t pursue her.  She’ll know who is really interested and who is not. And she won’t sabotage her chances with a man by confusing him.

Often this is not an easy concept for women to understand. Rather than using your masculine energy to make things happen or  commandeering the chase, put your feminine power to work. Smile, compliment, be friendly and appreciative, provide positive reinforcement for what you like. Tell him you had a great time or that you enjoyed talking to him. This is not aggressive – its warm and giving him the  feedback he needs to feel rewarded for his efforts.

Joanie felt providing this kind of feedback was exposing too much of her feelings and making her vulnerable. As a result, she resisted her femininity and felt more comfortable taking charge – but that was getting in her way. No wonder men didn’t ask her out!

After the session, Joanie agreed to try the more feminine approach. Now we’ll discover if Jeffrey is truly interested, or if he was just going along for the ride. And the chances that more men will ask for her number or for a date rise exponentially.

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 Meet Lots of Men But They Don’t Ask Me Out”

  1. So many women do all the chasing then wonder why the guy isn’t interested – of course he becomes lazy, he doesn’t need to do anything.

    Although in these modern times of gender confusion – women trying to be more masculine, taking on the male roles largely as there are no men around and men trying to work out where they fit and perhaps having to learn how to run a house when there is no-one else to do it… I do believe sometimes a nudge can help….

    eg If you think a guy is interesting enough that you might like to get to know him better, perhaps send him an sms giving youry number saying if he wants to catch up for coffee….. Sometimes this is the beginning of your life changing event!

    What some men tell me is they want to know they have a reasonable chance of succeeding before they will take the risk. So perhaps let the guy know you may be interested in finding out more!

    Be bold just a little, then let the guy chase you!


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