Dating After 40: Should a Woman Offer to Pay on a Date?

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Should I offer to pay on the first date?

One of the biggest questions singles ask me is, “Should a woman offer to pay on a date?” If you are an independent woman, you may have developed a philosophy that you don’t want to owe anyone anything. I get that believe me. I was single till 40 when I started dating in earnest. I had my own business and took care of myself completely. I certainly didn’t need a man to take care of me.

On my dating journey to find the man I married, I encountered many misconceptions single women share about paying and dating. See if any of these ideas sound familiar to you:

  • I earn my own money, so it seemed like I “should” pay.
  • Why should the man foot the bill for my beverage?
  • I have cash – who needs his?
  • That seems so old fashioned to just let the man pay doesn’t it?

This question of who pays, particularly on the first date, is actually much bigger than you think. You see, the way you interact with a man, from the time you say hello, sets a precedent.  Here’s the biggest lesson I learned about offering to pay:

You are potentially sending a signal that you’re not interested in him.
Oh yes, it’s true.

Think about it. What do you do when you don’t like a guy and don’t want to see him again? You just want to pay and get out of there right? Well that was true for me and for so many of my dating coaching clients. So, if you DO like the guy you just had a drink with, should you risk sending mixed signals about seeing him again? Well, that’s reason #1 why a woman should not offer to pay on a first date!

Here are some other crucial implications to consider about this question, “Should a woman offer to pay on a date?”

1. Just because a man pays for your glass of wine or dinner, doesn’t mean you owe him a thing
2. The pleasure of my delightful company is worth the price of a glass of wine or cup of coffee
3. Don’t have dinner on the first date so you don’t have to feel guilty about a big bill
4. Letting a man pay didn’t mean you give up your independence to him
5. Being treated feels good – it made me feel special and desirable

This last point is so important! As a dating coach I have seen time and time again that women who rush to pay are the women who are also the fastest to complain a man is cheap and never pays for anything. But you  see, you gave him that impression when you insisted on paying your share. Don’t do it.

One thing I tell all my clients is that the purpose of dating is to observe and gather data about a man and how you interact with him, to see if he is worthy of your time and emotional investment. But when you take action, you interfere with your ability to observe. You get in the way and give him something to react to. That’s not what you want. You want to know what a man would do on his own, without your meddling. That’s how you know if a man is truly generous.

Being independent is an awesome quality and men do like women who demonstrate this characteristic. However, if your independence sends the signal that you don’t really want a man because you can do everything yourself, including pay for the first date, that’s actually not so attractive.

Men want to feel wanted the same as women do. And good men, the quality men you long for who want the same committed, loving relationship that you do, they want to do nice things for their women. So please stop getting in the way or pushing men away.

Yes, you can pay your way and take care of yourself. But, in a relationship, the object is to add to your life not hold yourself apart. So, soften up a little. Let him into your world. Allow a man to do something nice for you and pay for that drink.

That softer side is your feminine charm and that’s what turns on a masculine, quality guy. Stop wondering if a woman should pay on a date. Definitely not the first date at least. Open up and let your femininity shine. The men you date, especially the right man for you, will love you for it.

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.

7 thoughts on “Dating After 40: Should a Woman Offer to Pay on a Date?”

  1. Agata,
    I have found when you split the check over the long run, it keeps you separated. Friends split checks. Most lovers do not. Better to take turns than split the check. It’s a psychological thing – when people only put in their half and never more – this can create problems. At least this is what I have noticed.

  2. Thanks a lot for ypur reply and all ypur help and this wonderful website. Why is it that splittingvthe check is not good?

  3. Hi Ronnie, that’s very interesting but i experience the other problem -after few days i don’t know how to offer to split. So for example soon i have a second date. The first was just a coffee, now he invited me for a dinner. Should i offer to split or just let him pay? I want to let him lead but also i know it may be a lot of money.

    • If the first date is coffee, that’s called “Date Zero” and not an official date. I wouldn’t offer to pay at dinner or contribute. He invited you, so he’s taking the lead. Let him have it. If you really want to offer to pay, do that on the second or third date. And don’t split the check, pay for the whole thing. Or buy drinks or movie tickets after. I have found that splitting the check with men is not a great strategy and can lead to problems. xoxox,

  4. I went out with a guy once – nowhere fancy, just an inexpensive cafe – and when the bill came he confessed he’d come out with only a small amount of money and not only did I pay for myself, but most of his share as well. I found this very irritating. What would be your impression of this? Mine was that he was not worth bothering about as he was a bit of an idiot. Interested to hear your opinion.

    • Hi Mel,
      I tend to agree with your assessment. He certainly didn’t plan well. Perhaps he’s the new gold digger that women have been accused of being for so long. Or he might have just made an honest miscalculation. Either way, he’s probably not the man for you. Don’t take it to heart, just move on to find better men.

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