. . . Not sure what a swingers flag is, but pineapples are generally regarded as hospitality symbols, so there are a lot around hotels, etc. It probably just means “Welcome”.

I think it needs to be upside down for it to be consider a swinger flag and this one doesn’t look rotatable given how it is affixed to the pole

The incredible swinging Shriners!

Yaah it’s most likely a welcome flag. Were grandparents in the northeast? There are tons of them on flags and on homes up this way. Has to do with how difficult it was to get them in the 18th century so they were symbols of wealth and welcome.

The swinging thing I have never heard of, but then again, I don’t pay attention to a lot of social stuff today.

I remember in my area, about 25-30 years ago, everyone was having these types of flags hanging outside, not pineapples, but the same style with the border. Not necessarily the swinging connotations of of these days. Did they ever go to Hawaii and talk about it a lot? Or, hey, maybe everyone is right, they were pretty hip.

“Pineapple Pride” flag. Used by folks to show they love Pineapple on their pizza.

From my understanding, swingers usa an upside down pineapple. Looks like that was hung right side up.

Went to an old cotton plantation years ago the tour guide mentioned pineapples. This article sums it up pretty well from what I remember the tour guide saying.

https://www.atlasobscura.com/articles/history-housewarming-pineapple-symbol

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Even among swingers, an up-right pineapple means you aren’t looking for more partners.