Dating Over 40: When He Wants You to Pay for the Pizza

Dating Over 40 or Dating After Divorce

Talking to my friend the matchmaker today, he told me a story about a guy who he’s working with. Now here’s a man who needs some dating coaching. Although, both parties might benefit…

Stu is 45, divorced for three years and looking for wife #2. He’s been with the matchmaker for 18 months looking for Ms. Right. Here’s what happened on his latest string of dates.

Date #4 with Sheila, the couple goes out for pizza. The conversation has been going well and it is date four, so they certainly like each other. Problem is, Stu was taken to the cleaners by his ex wife. So he has a bit of a chip on his shoulder about footing the bill for dating. Up until this point he has paid the bill when it arrived. But now, on date four, he wants to test the waters.

Picture this: The bill arrives for $26.95 covering a large pie, a beer and a soda. He looks at the bill and turns to his date, Sheila and says, “It would really help me out if you could pay for the pizza tonight.” Sheila (we can only imagine her thoughts) replies that she didn’t bring any money with her and so she’s sorry but can’t help him out tonight.

I’m surprised by both daters to tell you the truth.

First, Stu follows up the date with a letter stating he can’t date Sheila any more. A letter Stu? Really? As a professional dating coach for people dating over 40 or dating after divorce, this is where it would feel a lot better to never hear from the guy again vs. to get that letter.

I personally learned this lesson the hard way – DON’T SEND ANGRY, STUPID LETTERS! No break up mail please. If you can’t say it to the person’s face, just don’t say it. This is true only for the first few dates, not for months of dating. Different rules apply to a relationship than dating.

The matchmaker thought it was unbelievable that Sheila didn’t have any money. OK, I agree. Seems unlikely she had no money. But in Sheila’s defense, if Stu didn’t have money to pay for that pizza, he had at least two options:

1. Tell Sheila before they go out that he needs to go dutch-treat this week since cash is tight.
2. Don’t go out to dinner!

Springing his need/desire for financial help at the end of the dinner was horrible. It’s just WRONG. I remember being on a second date, when the guy asked me if I wanted to go back to his place for some afternoon delight. Uhhh, no. I declined. His reply was since I said no, my half is $12.50 for the lunch.

Me? Happy to pay and get the heck out of there. Or I could have told him “Too bad – your stuck and see you.”

From your dating coach’s perspective, Sheila had a right to be put off by his behavior. It’s not totally about the money either. Its about how the message was delivered. If Stu had told her the truth, that money was tight and they needed to go dutch-treat – she might have even offered to pick up the bill.

But Stu was demonstrating a deeper issue. Not about paying for a pizza, but the massive chip on his shoulder about how he doesn’t want to pay. He doesn’t want to foot the bill. And he never wants another woman to take advantage of him financially.

In the dating business, we call this BAGGAGE. Actually, everyone calls this baggage. Stu needs to work through his anger and money issues regarding women before he’s really ready to connect at the heart level. If you enter into relationship thinking you could get taken, chances are really strong that you will.

If a man asks you to pay for the pizza, you have several choices depending upon how you feel about him and what date it is:

1. If it’s date 4 or more, you really could pay for the pizza if your date asks nicely and prior to the date’s start
2. You might want to offer before he asks – at some point, it is time to contribute
3. If you have a problem paying, offer to pay half
4. If you don’t want to see him again, offer to the the date
5. If paying bothers you, or the way your date asked you bothers you, but you like him a lot, then go on another date to see what happens next time. It might be a one time situation and not a trend. You’ll never know if you don’t give the guy you like a shot and the benefit of the doubt.  Anyone can be short on cash once in a while.

photo creidt: Scott Feldstein

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: When He Wants You to Pay for the Pizza”

  1. I always take enough money to pay my own way and a bit over when I go out to eat. Would have been unexpected, unpleasant and our last date if this was me. Hopefully, would have made a graceful exit and no response to his letter. Poor gal…


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