My brother and I have had an uneven relationship. He was the “firstborn” - good-looking and whip-smart, but often too busy with his friends to even acknowledge me, the awkward kid seven years younger.

But in his early-20’s, my brother changed. He obsessed about losing his hair and became surly with me as if it were my fault that I apparently don’t have that baldness gene.

He’s now 38, married 17 years to a devoted woman. They have a son, age nine. I love the boy and regularly visit him to kick a soccer ball around together, and encourage his growing interest in music.

I’m 31, in a happy relationship with my girlfriend. But lately, I feel uneasy that something’s definitely going on badly and affecting my brother.

Normally, he earns a lot more than me, because he’s in real estate sales which have been soaring during the pandemic.

Also, his wife has a steady good income from her home-based job. Meanwhile, I’m a high school teacher doing okay for our needs.

Yet lately, my brother’s regularly asking to borrow money from me. Initially, it was $100 or so for something that my nephew needed - new running shoes, a ukulele, etc.

Lately it’s been more. He surprised me with a request for $2,000! My brother said he needed help with last month’s bills because they had to get a new air conditioner during the heat wave. His roof also needed repair.

I started to wonder just what he and his wife do with their earnings.

Years ago, my brother was playing the stock market beyond his means, and without much knowledge, and he lost a bundle. He borrowed from our parents back then, but Dad’s passed since and Mom lives on her pension.

Could he be doing this again, and if so, is it like an addiction?

I love my brother and would be happy to help as much as possible if there were true unavoidable needs.

But if he’s taking big risks on a gamble, I have to stop funding him. Also, I’m increasingly worried about how all this affects his son’s future. How do I handle this?

Worried Brother

It’s not easy to reason with someone who likes to take financial risks because they’ll always raise the stakes, as in saying that they’ll quit after the next big horse race, or a hot stock purchase that’s going to triple its worth, or in this case, maybe he’s into some other get-rich-quick scheme.

Time to talk straight to him. You cannot afford to cover his losses.

Whatever he is overspending on, he’s going to have to figure out how to pay his debts on his own.

If you wish, you can also set up a government-secured education fund for your nephew, in the boy’s name and yours only, to assure his future education. But don’t tell your brother about it.

Ask him what’s really going on, and tell him you’d love to discuss and help – but not financially.

FEEDBACK Regarding the “Unnoticed Wife” (August 26):

“It's possible that her husband (and the Unnoticed Wife) are as clueless as I was about how different people express and require love.

“My ex-husband had his own love language of "words of affirmation" and I definitely do not.

“Although our marriage crumbled for many reasons, I wish I had known then about love languages.

“Perhaps I could have been a more supportive partner and also better explained to him what I needed.
“Been there, didn’t do that.”

Reader’s Commentary Regarding the ex-husband who wants his ex-wife’s friendship (August 26):

“My wife and I were both divorced many years ago. I maintained closeness with my daughter who lived with her mother and stepfather. My second wife’s two children lived with us but their father made no effort to see them.

“My ex-wife and present wife were friendly although the ex’s husband didn’t want a relationship but tolerated it. My present wife insisted that I treat my ex’s new children as if they were family friends.

“Both my ex and her husband have passed. My wife and I have lived into our 90’s. All of my ex-wife’s family, children, grandchildren, nieces and nephews are what we call our family today.

“We recently moved into a retirement home and the young people who did all the work were children of that extended family. They all love us and we couldn’t love them more.”