Picking up tab is wearing thin

DEAR AMY >> I have a long-standing platonic friendship with “Brian.” He was recently diagnosed with a very serious illness.

I have always and often treated Brian to restaurant meals and entertainment. I have more than he does, and I am genuinely happy to do this.

However, lately, he’s asked me to take him and also his incoming visitor friend/cousin/grandmother, etc., to dinner.

I have no interest in taking people I don’t know to dinner.

I have paid a lot of money for all kinds of sometimes major expenses for him over the years.

The last time I paid for dinner, Brian sounded angry. He sneered and said we are “just a couple of gossips.”

It’s true that I talk about what is going on with me and mine. He also tells all in great detail.

To be honest, we’re both pretty boring — and so are our family and friends.

We all make mistakes. We are all human. I have lots of regrets, and I’ve always talked honestly about them.

I celebrate the good news I hear from him, and I feel sad when I learn about tougher events about his friends and family. And then I forget it.

We all are just living our lives and doing the best we can.

I am tired of being asked to pay for all kinds of things. Is that rude now that my friend has a serious illness?

If I do choose to pay for dinner again, what dinner conversation is now appropriate?

I guess if we are not allowed to compassionately discuss our friends and families, then we are left to discuss the news. I find the news pretty depressing.

Am I just a “gossip”?

— Upset

DEAR UPSET >> Your friend is seriously ill. This is bound to make a person reflective and occasionally grouchy.

When he remarked that “We are both just a couple of gossips,” he was referring to himself, as well as you.

I see this as a fairly common observation to make when you realize that the bulk of the conversation is usually about other people.

You should talk about it. Say, “I’ve always thought our conversations were pretty benign. I never judge anyone you’ve told me about, and honestly think we’re all pretty boring. But does it really bother you, or were you just blowing off steam?”

You’ve obviously been keeping a tab and have reached the end of your tether concerning picking up the check.

If you don’t want to treat others to dinner, you should be honest, and say so.

But yes, I would say that completely pulling the plug on this friendship now that your friend is ill is less than compassionate.

You say, “We are all just living our lives, doing the best we can.”

Ask yourself: “Am I doing the best I can?”