Just found out a boyfriend I had in high school passed away last October

I'd say for you it is beginning to happen. Now when I look up past acquaintances, I am surprised when I learn that they are still alive.

Because most of them are now gone, r1?

I was in my late 20s and early 30s during the height of the AIDS crisis and literally was losing friends and acquaintances on a daily basis.

An experience like that completely reshapes your views and outlook on life.

Condolences:

1) if you went to HS together and were friends before the relationship - yes - you can express condolences.

2) If you didn't know the guy before and after the relationship, no, do not express condolences to the family.

That is my take on things.

Yes, OP, this is what happens. Welcome to late-midlife.

OP, in the last few years, I've lost my Mom, a woman and dear friend who changed my career, my best friend to suicide, and, most recently, an older man who lived in my building; this means his caretaker, whom I'm close to, will have to move away.

This is a lot of loss in a short amount of time; I'm older than you, but I guess this is what we can expect as life -- and death -- goes on.

I'd express condolences to his sister, OP. Do you have happy memories of him, maybe one in particular? Tell her, then. It'll put a smile on her face.

I reconnected with a friend through Facebook. I knew her in high school through my cousin. I'd invite her along with my cousin to dances at my all-boys high school. Oftentimes my Dad picked us up. She told me that she remembers my Dad telling me, when we got to her home to walk her to her door and wait until she got in. She thought it was very gentlemanly of him to do this. My Dad died almost 25 years ago. The story brought a smile and a tear to me. So, contact your old friend's sister

The dying off starts in your 40s ,by the time your 60 (as I am) you barely notice it unless its someone you were very close to. About 10 years ago I went on a kick to find as many ex's as I could only to find out that so many were dead. I remember thinking "Jesus,Im not THAT old!" but then I just quit looking them up. Most depressing.

When I met my partner in 1981, between us we had 30-35 friends we saw pretty regularly. The last one died in 2004. Life in NYC back then killed three of ‘em (murdered, all random), ODs killed a couple, one died scuba diving, two of cancer, and the rest to HIV.

Welcome to the rest of your life, OP.

Did you know his sister? If you didn't end things nicely and didn't stay in touch, yes, I think it'd be weird to DM her and express condolences. Lord knows what version of your story her brother told her. Would be better to post a public message.

[quote]The guy who died last year I lost my virginity to.

Make sure to lead with this in the condole comments.

What did they die of?

r9 Did you live in the South Bronx? 3 murdered friends, even during the early 80's, is not normal. Maybe they were sex workers or drug dealers.

Did Susan Dey off her condolences, OP? Use that as your benchmark.

[quote]It's strange because I'm beginning to learn of people's death that I knew when I was young. I'm almost 49, and am wondering if this is about the age when it starts to happen?

If you're lucky and missed the 80s and 90s, then yes.

Since his death was many months ago, I wouldn't bother sending condolences. You were not part of each other's lives for many, many years.

If you think you might be mentioned in the will, then by all means make contact.

It's never inappropriate or too late to express condolences. A private message is fine, just say that you have only recently learned, you have many fond memories of time spent with her brother, and you are sorry for her loss. Nothing is weird about it, she doesn't need to know the terms of your separation or virginity. Even if he died alone with no friends, she will be heartened to learn that he had a friend. I've lost plenty of family members at this point and received condolences from many I've never met and I've been comforted by their thoughts.

“He loved getting rammed doggy-style. Anyway, sorry for your loss”

A former boyfriend died three years ago at the age of 61. We lived in the same town but hadn’t spoken in years.

Executive trainee, 29, shot jogging along the FDR Drive

VP, NY Life, 50’s, break-in, Stuy Town, throat cut.

Assistant Marketing Director, Pan American Airways, 41, bad trick.

All in Manhattan. NYC was different then. I hope it doesn’t revert that. It was great if you were young, but for a lot of reasons, it could be a dangerous place.

[quote] It's never inappropriate or too late to express condolences

That's EXACTLY why I send hand-written notes and wreathes to my husband's dead relatives. Thank you for your support

r12: I believe the woman died of kidney failure. I don't know what he died of, though.

Thanks for everyone's input. I think I'll just leave a comment on his condolence page.

"Assistant Marketing Director, Pan American Airways, 41, bad trick."

You mean she was prostituting on the side?

I’m sure the sister is sitting all alone just waiting to hear from another of her dead brother’s egocentric ticks, because, OP, this is all about you, isn’t it?

^tricks, not ticks.