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I think he’s cheap

Will I be able to get over how he spends (and doesn’t spend) his money?

Love Letters

Love Letters

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Q. 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. Soon after, we went on our first date to a coffee shop. 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). 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.”

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 Airbnb and the car rental, and he asked me to Zelle him 50 percent of the expense. I put my foot down and reminded him he makes a third more annually than I do and a has lot more savings. He 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 my daughter for the first time while she visited from out of town. At the restaurant, 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.” Then the waitress placed the check next to him. 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 and share a lot of things in common. He has expressed, from our second month of dating on, that he is very fortunate to have found me, that he loves me.

I feel that if we could work out the issue about his relationship to money, we could perhaps become much closer as a couple. He claims I am a financially independent woman, which he uses as the excuse for not splitting the expenses. 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?


A. The two of you could contribute a specific amount of money to a shared account for travel and fun. He could deposit a third more so it’s equitable based on what you have. Then, when the check comes or a plane ticket needs to be purchased, you could use that account without having to worry.

The thing is, I’m not sure he’ll sign up for that plan.

I’m not necessarily with your friends on this, but I do believe there is something inside of us that wants to treat people to things — or not. It doesn’t mean a person is good, bad, cheap, or the opposite. There’s a different kind of person who grabs the dinner check, not thinking about whether they actually have money in their bank account to cover it (that’s another kind of problem). I am notorious for handing a server my credit card before the check even comes — sometimes secretly — to treat a friend to dinner. That means I’m not even seeing what it costs! The chivalry gives me a high, but it’s not necessarily financially responsible.


You can teach this man your brand of generosity, but you won’t be able to change how he feels about mirroring the behavior. You want him to be someone who wants to treat your daughter. He might never be that guy.

Ask whether his philosophy about money has changed as you’ve dated. Also ask whether he’s saving for something specific. Maybe he’s more careful with money because he contributes to savings for his family. Perhaps there’s an expense you’re missing.

Find out how he feels after treating you (or someone you love) to something nice. Does it make him feel special? Helpful? Good in any way? Or is there resentment?

Those are the most important questions, really. If it’s the latter, and he regrets spending more when you ask, this might be insurmountable.



Fussing over dinner tabs, coffees, trips, etc., is minor league stuff. If you continue to date or marry, you will need an extensive playbook/rulebook/prenup as to home ownership, pensions, insurance, wills, and leaving estates to children, etc. Stuffy, annoying, petty, uptight Scrooge ... I would rather be alone.



No matter how wealthy or generous a person is, it’s always nice to not let them pick up the tab every time you go out. Even if it’s an inexpensive lunch, they will appreciate the gesture.


Your ex-husband was the same. Why sign up for more of the same? If a man I just met said he thinks I want him for his pension, I’d be insulted, not trying to fix him. Honestly, it sounds like you want a man who always picks up the tab no questions asked, and showers you with gifts. That’s fine, but this is not that man. You need to change your perspective or let him go.


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