'Southern Charm' Midseason Trailer: Shep Finds Taylor in His Bed and Craig Plays with Fire tram

The cast of Southern Charm is bringing the drama from Charleston to Jamaica.

PEOPLE can exclusively debut the show's midseason trailer, which sees the cast jetting off on a tropical getaway to the Caribbean, where exes Shep Rose and Taylor Ann Green wake up to an awkward morning after.

Shep, 43, calls Taylor, 28, "Miss Kissing Bandit last night," leaving fans to wonder: Did they or didn't they?

Later, Shep deems "single Taylor" a "dangerous" prospect — perhaps not least of which because she seems to also be getting flirty with newcomer JT Thomas, 38, who tells her: "I love you. I would marry you tomorrow."

While the group's vacation keeps them busy with boating excursions, snorkeling, sightseeing, waterfall diving and even a little flame-tossing on the beach for Craig Conover, they still find time to dig into drama — including the hot topic of Taylor's rebound hookup with Austen Kroll following her split from Shep.

"Do you want me to say that he f---ed me?" Taylor yells during one particularly explosive dinner scene.

"That is what happened," says Austen's ex Olivia Flowers, 31, shaking her head up and down. She's later seen crying over her friend's seeming betrayal.

Madison Le Croy, meanwhile, is still basking in the glow of her November 2022 wedding to husband Brett Randle. "Happy Madison is a good Madison," Shep observes in one scene, noting the 33-year-old's calmer, more easy-going demeanor since tying the knot — and moving on from her tumultuous relationship with Austen.

In a conversation with matriarch Patricia Altschul, Madison reveals she's already thinking of having a baby with Randle. "I would love to have a baby — but I remember bedrest. That's nowhere to be," she deadpans, referring to her pregnancy with son Hudson.

As for Shep, he's also feeling more relaxed and even-tempered these days — or, so he says.

"Pissed-off Shep is something that happens for two seconds and it's over," he declares of his new outlook, before the clip cuts to footage of him lambasting Austen, 36.

"You don't give a f--- about anyone except for yourself," he declares.

The trailer also hints at Shep exiting Charleston. "I have to leave town. I feel trapped," he's seen telling Patricia's son Whitney Sudler-Smith, 55.

While Craig's girlfriend Paige DeSorbo, missed out on the Jamaica trip, the two — who have been long-distance dating since 2021 — have been having serious conversations about their future.

"I want a wife and family," Craig, 34, tells Paige over dinner, prompting the Summer House star to make a face and say "ew" before taking a sip of her wine.

However, it seems she might come around to the idea. "Let's put a ring on it," Craig says, before the clip cuts to Paige, 30, admiring a huge sparkler on that finger.

The trailer ends with the cast gathered together outside, all wearing tin foil hats on their heads. "A lot of people say that conspiracy theories are dangerous, but knowing the truth is never dangerous...," Craig says, foreshadowing more revelations to come among the group.