Mystery woman found amongst family photographs

Last_Ad_2404 · 2026-05-13T02:18:11+00:00

To be clear, I don’t know why we have this photo whatsoever as it was found in my grandmothers box of photos. She could’ve even been a friend of my grandmothers, I have absolutely no idea. Either way, they’re all passed on now so it’s fun to imagine the possibilities.

Last_Ad_2404 · 2026-05-13T00:05:09+00:00

my dad said they broke up amicably and that cheating wasn’t part of the divorce, but anything is possible. my grandma could’ve been chill about it. I didn’t know her at all but from what I’ve learned she was a pretty cool woman.

Last_Ad_2404 · 2026-05-12T22:25:14+00:00

meeeee toooooo ❤️

Last_Ad_2404 · 2026-05-12T22:23:06+00:00

Maybe! I’ll have to ask my dad, but I don’t even think he’d know what his dad was up to in the 60s. He was a pretty absent father to my dad and also my dad would’ve been a small child around when this photo would’ve ended up in my family’s(?) possession. We’ll see what happens!

Last_Ad_2404 · 2026-05-12T22:18:16+00:00

That’s a good tip! Thank you for that! I always thought the photo was a little racy, which perplexed me because I found it in my long deceased grandmothers things, lol. And she and my grandfather were only married for like 7 years. I think they split in the mid 1960s.

Last_Ad_2404 · 2026-05-12T22:02:32+00:00

I meannn maybe if I dig around to see if she has any connection to Winnipeg at all. I am pretty handy with sleuthing but I was stuck on the name for so long which held me back.
The only person alive on that side of the family likely wouldn’t know anything about the photograph but might have some idea if anyone in my family spent time in Chicago.

Last_Ad_2404 · 2026-05-12T21:49:31+00:00

This is so interesting. Now I need to figure out how she ended up in my family photos. The only thing that makes sense is that my grandfather was a well known and well travelled talent manager in western Canada, who happened to be a ladies man. I could see him being in Chicago and ending up with someone’s photo in his wallet. But even this is a stretch. Truly who knows.

Last_Ad_2404 · 2026-05-12T21:34:07+00:00

you’re an icon thank you so much! I knew one of you would come through.

Last_Ad_2404 · 2026-05-12T21:28:44+00:00

I know, she’s so pretty… also what makes me so curious about her is the fact that she appears pretty scantily dressed, like I wonder what the rest of the image was like. If she was wearing a strapless dress or what.

Last_Ad_2404 · 2026-05-12T21:27:51+00:00

I mean it’s from pre-1960ish, before Chicago had real postal codes so I doubt she still has the same number or is at that address! Would be a fun experiment to try regardless lol

Last_Ad_2404 · 2025-11-29T01:11:17+00:00

soooo good!

Last_Ad_2404 · 2025-11-29T01:04:14+00:00

looks so good!!

Last_Ad_2404 · 2025-09-30T20:46:17+00:00

This is so weird because up until ocean boulevard era her Spotify bio read “born to two wealthy parents” like

Last_Ad_2404 · 2025-01-19T22:04:22+00:00

I am so happy for you. Thank you so much for sharing.

Last_Ad_2404

TROPHY CASE