I met my best friend in high school, when we both showed up for football tryouts. He was taller, I was faster. Luckily, the coach wanted us both on the team.

We went to the same university, lived together on campus, then moved to a neighbourhood house shared with other students.

When my sister visited us for a football weekend, she and my best buddy took off for half a day without me. She wanted “to see the town,” I was told. I already knew better.

They got engaged when he and I graduated. My then- girlfriend was at another university, but arrived for the ceremony. She warned me that day that my sister wasn’t committed to my best friend. I got angry and didn’t believe her. We almost broke up over it, but I now think it was because she knew the truth.

Flash forward five years. My friend got a great job while my sister insisted she wasn’t cut out for a career or for raising kids. Instead, she spent their money on expensive clothes and hung out with like-minded friends in high-priced restaurants.

I loved my sister when we were kids but saw her become totally self-centered in high school, always looking for “fun.”

Recently, after her husband returned too early from an out-of-town conference, he found her at home, cheating with another guy.

I’m shocked, angry, embarrassed and hurting for my best friend. I can’t forgive my sister for her disregard of their marriage vows, yet it’s really no surprise. She was always on her own path.

Now, if I badmouth my sister, I’m disloyal to family and my parents will be terribly hurt. But if I support her, I may lose my long-time friend. How do I handle this situation?

In the Middle

In this delicate situation, the “middle” is the worst place to be. You’re a man with two important but different loyalties here. That’s an inescapable fact.

Talk to your sister if she’s open to it, but don’t pronounce judgment. She’s an adult who wanted out of that marriage, whether she said so or not, and for her own reasons which she may or may not share with you.

Talk to your friend, as soon as you can. Be clear that you had no inkling of your sister’s involvement with another man. If your friend shows that he’s very angry, recommend that he talk to a professional therapist. Above all, stress that you still consider him your lifetime buddy.

It may take some time for emotions to settle on both sides. Meanwhile, your connection to both parties calls for not repeating their personal stories to others who might question you.

Reader’s Commentary Regarding the statement from a reader (March 29): “My 30-year marriage is a mistake. Should I tell my son?”

“I appreciate the advice you gave. When I was in my early twenties, one parent left my other parent and told me that the marriage was a mistake, and if they could do it all over, they would ‘never have had children.’”

“I’m certain that my life is a gift (and I know my parent loves me despite the short-sighted comment.) It’s fine to have feelings and opinions, but much of the time keeping them to oneself is the smartest, kindest thing to do.”

My father died two years ago. Me and my brothers have tried to fill the void in my mother’s life. She’s 75, in good health. They were together since she was 20. She’s very pleasant, kind and generous.

She has several close friends whom she doesn’t see often due to distance. She’s happy, but understandably lonely now.
I want to help her find friends and more connection. I want her to be happy without carrying so much lonely heartache.

I’ve never had online friendships or relationships. I doubt my mom would want to develop connections online.

How can I help her connect to other people in the real world?

 A Loving Son

Wherever your mother lives, there’s likely a seniors’ program in the larger neighbourhood, and/or a faith group of her interest, or a dance and movement class that welcomes seniors.

Check online information for available recreation programs that you and your brothers can take her to see.