Dating Over 40: Most Men Want to Pay

What’s the top question women ask me about dating? Well, after “Where can I find a decent guy?” the most common question is – “Who pays on the first date?”

Now I am happily married, but this was an unusual week because I did a lot of networking. Six one-on-one sessions, plus two big events.  The biggest surprise is what happened when the bill came at the two lunches and three coffee dates.

The big shocker – four out of five men paid!  I took out my cash (after all these weren’t dates – if you know me, you know I don’t believe in a woman paying on the first date) but it was harshly refused in the four instances when the men paid.  Each man strongly insisted that I  “Put it away.”

The fifth guy said – “You want to split it?” Of course I did. I was totally ready and willing to pay my share.  After all, this is business.

I started to think about all the women I’ve spoken with about this topic. Women who insist  they must at least offer to pay.  But 4 out of 5 gentlemen looked at me like I was crazy to pull out my wallet.  And to Mike, Matt, Stu and Jeff, let me publicly say – THANK YOU.  Thank you for reinforcing my belief that men want to treat women well. That men expect to pay.  That men WANT TO PAY.  In fact, I believe it makes them FEEL GOOD TO PAY.

Who are these guys?  Well, of the Payers, four are married and between 40-60 and one is a single 23 year old.  (I thought he was 28.) Mr. Split-the-Check is in his early 50’s and single and he’s the one who knows me best.. Go figure?

With this new experience in hand, I want to reinforce and once again recommend that for women on a first date – keep it in your purse – your wallet that is.  No need to whip out the cash at the end of a meal or coffee.  Relax.  Because if he wants you to pay your way – he’ll have no trouble letting you know that. 

Honestly, it was nice to be treated like a lady out there in the world at large. Can I please encourage you to try it?  Go ahead.  Make your day (and his) and LET HIM PAY.  I think its pretty clear, 4 out of 5 men prefer it that way.

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.

2 thoughts on “Dating Over 40: Most Men Want to Pay”

  1. Hi Anna,

    Feel free to do what you want. I share what has worked for the majority of the 1,000 women I have worked with. You may have a different experience.

    If you look closely, you’ll see that my post uses the word “strongly” not “harshly” which is very different. These men weren’t overpowering me – they were demonstrating their desire to please me – chivalry not authority.

    My life is all about questioning authority – so I do not succumb easily believe me.

    Learning to receive and allowing men to be men (at their best) is an important step in finding a loving healthy relationship. You might want to consider giving a man a chance to please you rather than insisting on being the chick-in-charge. Let me know how it works should you decide to give it a try.

  2. “…it was harshly refused in the four instances when the men paid. Each man strongly insisted that I ‘Put it away.'”

    Hmm. Regardless of who pays, I have to say I’m NOT attracted to a man who “strongly insists” that I do anything, especially on the first date. Authority is a valuable trait in business, but not on a date.

    And personally, paying on a date makes me feel good. Why, then, shouldn’t I do it?


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