Lucy was the first friend Kristen made in KW. Working and living together, they became “The Real Housewives of Key West” and invented “SnapBack Sundays” at Blue Heaven. Lucy expanded Kristen’s world and their adventures have been endless.

What started as a tremendous dislike of each other based on first impressions, quickly grew into the strongest friendship imaginable. As roommates for nearly a decade, (in some states, they would be considered common law married) Tom and Alvin share a profound love and admiration for each other.

Becoming besties in middle school, their friendship has spanned time and distance. Chriss has given her 1,000 haircuts while Kristen sang show tunes on a toilet seat for years. They love the Chicago Bears, and hope they crush the Packers forever and always.

Tom first saw Dan at an Open Mic, and liked him immediately. Tom loves the way Dan’s carefree spirit and hilarious perspective almost disguise his intelligence and thoughtfulness.

Daria and Kristen share a secret language only they can understand, after many cocktails summoned it awake. They have a love for dark humor, film, art and festivities. And they are both giant nerds. But cool nerds.

Tom met Landry at the Great Canadian Laugh-Off, and knew they were kindred spirits when they both ducked-out of the T.V. taping to have a beer at the bar. The friendship that started with that beer, continues to this day, 15 years later.

Alena and Kristen have shared many adventures together on the water, and traveling abroad. Whether it’s playing Thundstruck, tickling lobsters or zip lining through a cloud forest-they always manage to have a great time.

Tom and Joe met in the Boston comedy scene, over two decades ago. Joe moved to Key West and Tom went on the road, but they maintained contact and eventually came together again, to build Comedy Key West!

Jill and Kristen’s friendship began watching a Rob Zombie film, and their love for horror flicks, adventure, and crazy Key West nights. After almost 10 years of friendship, they also became roommates, bringing them closer than ever before.

Tom met Steve while performing at Comedy Key West, back when it first opened. As Tom’s youngest close friend, he admires his big heart, his enthusiasm for comedy and has dubbed Steve as, “The Hardest Working Man” in Key West.

Britannie and Kristen met at Blue Heaven, cruised the seas as cabin mates, and got matching tattoos to remind them there are few people who will ride a struggle bus with you, through thick and thin…although sometimes it’s fun to also drive the bus!

Even though they have known each other for 25 years, Tom and James didn’t become close until James moved to Key West. He became an integral part of Comedy Key West, and a great friend to both Tom and Kristen…when he’s not trying to “karate-chop” them.

A huge part of Tom’s life for the past 25 years, Joe’s one of the main reasons Tom ended up in Key West. Early in their friendship they visited Key West and created lasting memories that eventually drew Tom back to the island.