The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

Key West conversation starters

At a loss for what to say? 5 Key West conversation starters

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


For all its vaunted One Human Family mantra, Key West faces the same challenges as the mainland real world when it comes to polite conversation. No matter what one opines, one will most assuredly encounter rolled eyes, raised eyebrows and a grouchy “Yeah, but” even among like-minded friends. Finding conversation starters that don’t raise hackles takes an extraordinary effort.

As we head into the family-and-friends holiday season, I’ve been making a list of Key West conversation starters that might — and I stress might — keep the “Don’t let the door hit you on the way out” moments to a minimum.

The weather. Boringly safe for all audiences with enough nuances to keep the conversation rolling for half an hour. Nov. 1, marked the end of Grumble Season because that’s the day I turned off the air conditioner and opened all the windows. We’ve spent the past four months grumbling about the weather, worrying about hurricanes and generally being irritable because we were so done with sweating through our clothes four times a day. Hardly anyone hates Key West’s fall and winter weather, so it’s your number one safe topic for Thanksgiving.

Well, there is an exception and it’s bound to come up: How in the world do visitors stand that cold ocean water? I see them neck deep in January when the water at Fort Zach is 69 degrees and their lips aren’t even blue. Even with a wet suit, I’m not going in and there they are paddling about in a swimming pool that’s heated all the way to, say, 82. (I don’t do pools under 87.) Just nod politely and say “it’s all relative.”

Parking stickers. We have reached “drama free” on the 2021-2022 Key West parking permit hyperventilation, so it’s safe to start a conversation with “Mine arrived in the mail today. I know it will be easier next year.” Two weeks ago, we were yelling on social media and writing flame-throwing emails to the overwhelmed staff at City Hall as they tried to cope with a balky, user-unfriendly online system and get the stickers in the mail. Consider this a public thank you to parking czar Jim Wilkins and staff, who wrestled this one to the ground. My lovely new, hot pink decal is on the windshield.

Iguanas and chickens. You might not want to bring up either when visitor ears are nearby or your animal rights buddy is on her soapbox, but for the rest of us, any conversation about nasty iguanas and bothersome chickens will sustain a decent give-and-take. Advice: Don’t mention either over food. The conversation can get, let’s just say, messy.

Sunset. A Key West sunset is an experience wrapped in a mythological phenomenon of nature. Let’s go watch sunset is an invitation few refuse — even a nondescript Key West sunset off the White Street Pier or the corner of my backyard.

Well, that’s all I’ve got. I thought there’d be five things we could talk about. Seems not. Perhaps a list of questionable topics?

Here are my top 10, which became 12, guaranteed to start a food fight, even among friends:

Key West things we ought NOT discuss at happy hour

  • Cruise ships.
  • Single member voting districts versus at-large districts. Term limits.
  • Covid, masks and vaccines.
  • Parking. (Except for the pink sticker, which we all love if we have one.)
  • Vacation rentals.
  • Sidewalks.
  • Planes, cars, scooters, e-everything-on-wheels, bikes, pedestrians in crosswalks.
  • Duval Street. Empty storefronts. Storefronts and establishments with unpleasant merchandise and messages. Untidy crowds. Cheap tippers.
  • Trees.
  • Re-Anything. You know, like re-paving, re-novating, re-imagining, re-negotiating.
  • Airport.

Yeah, I know that’s 12. And, that’s before we open the list to state, national and global matters. And before we add religion, education and Uncle Harry. Heck, if I sit here a few more minutes, I could dash off another couple dozen. You could cut and paste these onto a poster for your front door. Sort of a warning to your holiday guests.

Waste of time, my friends. We’re going to grouse; it’s what humans do. As my mother always said when I’d whine about some Key West infraction: “Yes, but you live in Key West.” And, that makes me smile. Come to think of it, I should go back and add it to the five things we can talk about over happy hour and holiday dinner.


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