I am almost 60 years old. I was married for more than 20 years and I have been divorced for almost as long (I got married young). Once both children left the nest for good last year, I finally joined MeetUp. I had the best summer of my life by going hiking, kayaking, wine tasting, boat riding, etc. In one of those activities I met “B,” a guy who seemed suspicious that I was a single woman who wanted to live off his pension. I was not even looking for a date! I quickly dismissed him as not dating material, even if I decided I was ready to date in the future.

A couple of MeetUp activities later, he showed more interest and a kind and generous side. He asked questions about me. Soon after, we went on our first date to a coffee shop. When I ordered my coffee, B made no gesture whatsoever to pay for it, so I paid for my coffee. I attributed this lack of chivalry to his lack of experience dating since his divorce 10 years prior. As we have been dating now for months, his lack of chivalry (or generosity) has become a huge issue for me.

Early on in our relationship I shared with him how annoyed I was by my ex who would seldom take me out to eat even while married (we are friends post-divorce and he still does not). My ex would pretend not to see the waiter drop the check on the table or, if he saw the check, he would pick it up, see the total, and promptly return the check to the table for someone else to pick it up. I also shared with B that when traveling with a family member, whose income is twice as big as mine, she expected to share the expenses 50-50. I clearly remember B saying “that’s not fair.”

I told B my love language is acts of service, and that includes being treated out to dinner. Since he comes over to my house three to four days a week and always eats at least two meals a day made by me, I told him I’d be happy if he, in return, took me out to dinner once a week. He did so for three weeks and then it stopped. Once I asked him if he could pick up something to eat at the supermarket for us because I’d had a long day and was too tired to cook. He came empty handed because he could “not find anything.” So I said take me out to dinner, and he did, but I never heard the enthusiasm behind the invitation.

We have gone on two out-of-state excursions. It was at the end of a work-sponsored conference he attended, so his employer paid for B’s airplane tickets. I paid for my own. I asked him before and during the trip to discuss how we were to split the charges, and he insisted we’d talk about it after the trip. Well, he did. At that point he produced a detailed breakdown of the price of the Air B&B and the car rental, and he asked me to Zelle him 50% of the expense. During our weekend excursion last week, I put my foot down and reminded him he makes a third more annually than I do and a lot more savings. So, he kind of reluctantly agreed that I should pay $150 out of the $400 for lodging. After that, we split everything down to gas, and I brought my own groceries.

This week he met one of my kids for the first time while she visited from out of town. I told him I was going to go out to a restaurant with her and that we would like for him to join us if he wanted to meet her. When the waitress came to the table and asked whether it would be one or separate checks, B was mum. There was an uncomfortable silence, so I responded “I guess it will be one.” At the end of the dinner, the waitress placed the check next to him. He left it on the table. Again, there was a terrible uncomfortable 15-second moment, and then my daughter said she’d pick up the check. I insisted she didn’t, so finally B offered to pay.

B and I get along very well as travel companions when it comes to doing activities together. We share a lot of things in common, we enjoy the great outdoors, we love biking together, going on hikes, enjoying nature. He is a great gardener and I love plants. He has planted things for me. He has expressed, from our second month of dating on, that he is very fortunate to have found me, that he loves me, that he is committed to me, and that he is in love with me. I am more realistic and, although I love his company, I see him more like a friend that I enjoy having around. And we are very compatible in bed.

I feel that if we could work out the issue about his relationship to money, and how it affects me in such a negative way, we could perhaps become much closer as a couple. People tell me to cut my loss and move on. That a 60-year-old will not change his ways. I disagree. I think he is accustomed to being a cheapskate but that I can, by way of example and by setting guidelines, teach him a better way. I need your advice urgently. He claims I am a financially independent woman, which he uses as the excuse for not splitting the expenses in a fairer, equitable way (based on our respective incomes), or for not offering to cover the entire expense all together. He and I both are debt free (our respective homes are paid for). He expects to retire in the next two years. I still have five to go. Is there a good formula for couples to establish who pays for what and when?

– Paid