I was recently chatting with an old friend I haven’t seen since high school. We bumped into each other at a coffee shop and spent about 30 minutes reminiscing. Out of nowhere, she reached her hand out to mine and said how sorry she was that so-and-so had passed away.

I was in complete shock! I hadn’t heard, though it had been a few years prior. And the person in question had been my first love, my high school sweetheart, my first everything! I was rocked!

The conversation moved on quickly, we said our goodbyes and went our separate ways. But now I’m obsessed with this information, looking him up on Google, trying to remember every word we ever said to each other.

Would it be wrong to reach out to his family? His parents and siblings? I haven’t seen or spoken to any of them in over 15 years.

Gutted

It depends on what kind of relationship you had with his parents and siblings. If you were that close with his sibs, I’m surprised they didn’t reach out when he passed. If you weren’t that close, then why would you reach out to them? Especially so many years after the fact.

However, if you can keep it together, then there’s no harm in reaching out. A parent never gets over the loss of a child, and to hear from someone who loved their child might give them some warm feelings.

But first, you need to make peace within yourself with this loss.

I’m the eldest son with one sister. She and I have battled over her and her adult son living rent-free in our parents’ home. Her son is a freeloader.

I quit school with my parents’ approval, worked and paid $40 a week in rent to them for six years; then l rented my first home, for a decent monthly rate. Now my sister’s son lives rent-free, when l believe the house should be sold before tariffs cause its value to crash.

My dad passed years ago. They gave his coin collection to my nephew and our relationship has disintegrated. The amount of money that is wasted drives me nuts. Mom lives with my sister and her husband but for a person that grinded every penny into a dollar, the waste she overlooks is irresponsible.

So why do people get crazy over settling an estate when a parent is still alive? The simple answer is the Gambling Partner. My net worth is high but with no kids, my estate will go to charity before I leave anything to my ungrateful family.

Left Out Will

I’m not sure what your question is here but I can see that you have a complicated relationship with your sister, her son and your mother. So let me try to help.

Your mother is obviously a senior and living with your sister and her family. Let’s assume they look after her properly. Still, try to spend time with her at least weekly. Take her out for a meal, to a show, for a walk in the warm summer evenings, so you can get her out of the house and get some private time with her. Hopefully she’ll feel safe to tell you if anything is amiss at home.

As for your sister, she can’t be enjoying life with a gambling addict. Show her some compassion. Maybe living rent-free with your mom is the only way she can secure a roof over her head. And maybe having her son living with her keeps her safe from her addict partner and helps with your mom.

Since you’re financially secure, why does it bother you so much? Try to let it be.

FEEDBACK Regarding the widower and a new companion (Nov. 28; Feb. 10):

Reader – “I’ve been a widow for nine years. If any man I was involved with suggested I get rid of my husband’s picture, I’d suggest he could show himself out.

“My mom died when I was in my late teens. My dad was married to my stepmother for 25 years before he passed. Someone asked her once why she didn’t get rid of photos of my mom. Her response, ‘They were married for 37 years.  A life together that can’t and shouldn’t be erased.’

“However, I do agree with ‘except in the bedroom.’”

Lisi – Your stepmother sounds like a thoughtful and caring person. You’re fortunate she came into your father’s life. A healthy relationship recognizes that both parties have a past. Unless sordid, ugly or painful, there’s no reason to erase its existence. Our past shaped us into who we are at present.