Asking Eric: We gave a homeless man $200, and I didn’t foresee how he’d spend it

Dear Eric: During our morning walks, my husband and I became acquainted with “Ron,” a homeless man who always sits on the same bench and always has a cheery hello.

During the holiday season, we decided to gift him a box of homemade cookies and a Christmas card with $200 in cash slipped inside. I’ve imagined him treating himself to a decent dinner or buying something nice.

We knew nothing about Ron, except that he seemed sweet and sober and appreciated our little gifts.

Recently, from several reliable sources, we’ve discovered that Ron has been sending money, including his VA checks, to a woman in China in the hope of getting her to come to America and marry him. People have repeatedly tried to tell him that this is an internet scam, but he refuses to listen.

I find it upsetting that our money is being handed directly over to a scammer somewhere. My inclination next holiday is to continue to hand him the cookies and the card but not the cash. I figure it’s just $200 less for some heartless con artist to steal.

My husband, however, objects. He says it’s none of our business how Ron spends his money. If this gives Ron purpose or pleasure, then who are we to interfere? Our reward should be in the giving and nothing else.

My compromise is to give Ron a gift certificate, perhaps to a grocery store, but my husband feels that even this safeguard is too judgmental. What is your opinion?

– The Christmas Judge

Dear Judge: We don’t get to choose how other people make use of our gifts, especially strangers. Since you don’t have a relationship with Ron beyond these very generous gifts, you’re not in a position to safeguard him.

I’m not wagging my finger, but it’s notable that you know nothing about him and you heard about the supposed scam from others, not from Ron. He’s not shared this part of his life with you.

What you might do is ask him, “What do you need?” or “Is there someplace from which you’d like a gift card?” This way, you can be more confident that you’re meeting him where he is without trying to police his spending.

Dear Eric: I have a friend who is driving me and other friends to the brink with her persistent negativity. This has been going on for years but is much worse lately.

We are all retired, and this friend is substantially better off financially than the rest of us. Despite this, everything is a litany of “poor me” and nonstop negativity.

No one else has suffered grievous losses as she has (we have). No one else is as burdened with problems as she is (we have our own issues, and deal with them). No one experiences as much pain, suffering, loss, misfortune or tragedy as she does.

Literally every conversation ends up being her listing a multitude of problems, all featuring her as the victim. When we try to gently point out that she is financially secure, or has many blessings to be grateful for, it’s just a doorway to yet more complaining, whining and “poor me.”

It’s clear she’s depressed, and it’s also clear that the medications and counseling she’s receiving are not helping. We’ve tried patience, listening, kind boundary-holding on topics, and redirection.

It’s to the point where some friends have stepped way back from the relationship, and where several of us are questioning why we continue on. This woman can be kind, generous and caring but rarely, and there’s little joy in any of our relations with her. Help, please.

– Overwhelmed by Negativity

Dear Overwhelmed: It sounds like you’ve been very empathetic toward your friend, while also communicating – in many different ways – what you need from her.

One of the tactics that strikes me is boundary-holding. Presumably you’ve said to her, “Complaining about this subject is not something I’m able to listen to right now,” or something like that. And, presumably, she’s ignored that.

When people aren’t willing or able to honor the boundaries we’ve set, it often becomes necessary for us to take a step back. You can tell her this. Indeed, while it may be uncomfortable, it’s better to be upfront than to drift away. You can tell her that you care about her and you value your friendship, but specific parts of it aren’t working for you right now and you need to take a break.

In all likelihood, this will be added to her list of complaints. But there is a chance that she’ll hear what you’re saying and try to change her behavior. Her outlook may not change, but right now the substance of your friendship – at least from your perspective – is all negative. She can choose other things to share.

Send questions to R. Eric Thomas at eric@askingeric.com or P.O. Box 22474, Philadelphia, PA 19110. Follow him on Instagram @oureric and sign up for his weekly newsletter at rericthomas.com.