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.

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?


Leave a Comment