Dating Over 40: When Was the Last Time a Man Tried to Pick You Up?

Dating After 40 & Dating After Divorce

For me, it was yesterday! I am constantly amazed how I am living proof that you don’t need to be tall (I’m shy of 5 feet), thin (definitely not) or young  (I’ve stopped counting) to have men flirt with you, try to pick you up or tell you that you’re beautiful.

There I was, walking from where I parked my car to a meeting downtown. I don’t live in a big city – downtown is a lovely suburban green in traditional Connecticut style.

Half way to my destination, I was joined by a tall, slim, good looking guy of no more than 22. (He looked very young. ) Here’s how the conversation went:

Him: “You are really beautiful.”

Me: “Thank you. How nice.”

Him: “Are you married?”

Me: “Yes I am.”

Him: “Why is it that all the good ones are taken?”

Me: “Oh I know how that can be.”

Him: “Would you go out with me any way? Maybe we could go out for a drink sometime.”

Me: “No, I don’t think so.”

Him: “Well, just talking to you has been good. You really made my day.”

Me: “You made my day too.” (How many 22 year old guys have tried to pick me up lately?)

Him: “I did? Wow. Can I get your phone number then?”

Me:  I laughed.

This isn’t the first time this has happened this year! Over the winter I was at Barnes and Noble with my husband on a cold Sunday afternoon. A man walked by me (my husband was in the men’s room), looked me right in the eye and said, “You are really beautiful.”

Then he walked away. Who does that? He didn’t try to pick me up. It was like a compliment drive-by, leaving me feeling warm and tingly all over.  This kind of thing doesn’t happen often to me, but it does happen. As your dating coach, my question to you  is, when was the last time a man tried to pick you up?

I’m not trying to make you feel bad if  you haven’t been the recipient of some blatant flattery. My point is, can you imagine it happening? Are you open to it happening? And how would you feel if it did happen?

This is where flirting can make a tremendous difference. Men approach you when you seem happy and friendly. When your body language conveys you are approachable and open. For example, would you have bothered talking with this young man or kept to yourself hoping he would go away?

See to me, flirting with him was fun! It made me feel good. He claimed it made his day. I got to tell a great story to friends and make them laugh. I used the incident to write this blog post. To me, this is fun.

Now I know I’m no longer single and looking. But truthfully, my way of handling this hasn’t changed must just because I have a ring on my finger. When I was single and started to seriously look for Mr. Right, this happened on the rare occasion. Initially, I pretended to be married as a way to make a quick exit.

However, once I realized this situation was a way the Universe  could provided me with  feedback on my “attract-ability, I learned to open up and enjoy it. That’s why I still enjoy it today.  After all, what’s not fun about being told you’re beautiful?

Here’s another crucial thing to keep in mind about this situation, particularly true if it happens at a singles event. Other men are watching how you react and interact. Oh yes, they are! The quality men who aren’t players, who don’t have their pickup lines perfected, they hang back to see how you respond to the bolder men.

So, are you friendly? Or do you act disgusted, offended or even bothered by these men?

If a man isn’t your idea of perfection, do you turn away or tell him to get lost? As your dating coach, I strongly advise you to think twice before you react. Because the good guys are watching you to see how you handle yourself. And if you are mean, rude, or appear unfriendly and unapproachable, say bye bye to the good guys.

Frankly, I hope some guy does find you SO attractive that he has to tell you this. And when it does happen, please remember, this is the Universe  reminding you that you are one hot mama, men find you attractive and there are more and potentially better men where he came from if you can muster a smile and take in the compliment.

Photo Credit: kate e. did

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

3 thoughts on “Dating Over 40: When Was the Last Time a Man Tried to Pick You Up?”

  1. This is nice tips for the ladies. my major problem is that many women above 40 always find me attractive even to ask me for quickie. … finding alder women attractive and experienced.


Leave a Comment