Shep tries to right his wrongs from Auldbrass and invites the gang on a trip to St. Simons Island, but his efforts are in vain when his emotions get the best of him. Austen expresses concern for Taylor’s future with Shep. Craig loses his temper when Naomie’s actions bring up wounds from the past.

The gang takes a much-needed break from Charleston and heads to Auldbrass, an estate designed by architect Frank Lloyd Wright; Naomie divulges her new love interest to Leva and Austen, who prove they are not the best at keeping secrets.

The wedding countdown begins for Lil Craig and Peaches. As Shep opens up to Whitney about his marriage fears, Austen sulks when Olivia arrives with a blind date. Craig and Naomie bump heads on boundaries. Maid of honor Madison and best man Austen bump heads.

The holiday season is off to a rocky start when the gang gets together for a Friendsgiving feast. Austen hosts and leaves certain people off the guest list. A newly single Kathryn searches for things to be grateful for. Paige comes to town, and while Craig imagines what it would be like for her to live in Charleston, not everyone is ready to give thanks for her presence.

Patricia invites the guys over for a gentlemen’s dinner. The ladies get together for a night out on the town. As the girls take the time to face their issues head on, a faux pas at Patricia’s leaves Craig in major debt. Shep’s honesty comes into question when past secrets surface online.

‘Tis the season to start some drama! Craig prepares for his Sewing Down South Holiday Gala and faces difficult decisions with the guest list. Shep reflects on his actions toward Taylor and proposes an idea that leads some to question his intentions. Venita worries about the state of her friendships with the group. Austen and Olivia make strides in their relationship while one guest takes bold strides on their way out of the party.

Madison shocks the group with rumors about Olivia. Kathryn sets the record straight on her relationship with Chleb. Taylor puts Shep on blast and Olivia puts Austen in the hot seat, but an emotional discussion brings everyone to tears together.

After being excluded from Olivia’s oyster roast, Venita looks within and spends time with her mom in hopes of gaining insight to her family’s secret past. Craig may have a new secret of his own when he goes against Paige’s wishes and meets up with Naomie. Wedding bells are in the air for Shep, though not in the conventional sense.

Tensions continue to rise on the group's trip to Auldbrass; Craig demands apologies; Olivia wrestles with her feelings about Austen; Whitney deals with the repercussions of breaking bro code; an egg toss scrambles Shep and Taylor's relationship.

Madison and Venita's joint party takes a turn for the worse; Paige sets ground rules for her relationship with Craig; Shep struggles to get Taylor to trust him while he's away; Kathryn sets up a girls night out to celebrate her new status.

Shep and Craig help Austen move things out of his childhood home; Taylor voices concerns about Shep's past infidelity back in Charleston; Olivia prepares to throw an oyster roast, and one guest's presence causes Austen to spiral.

After a tumultuous year, the Charleston crew is back and ready for a fresh start; Kathryn throws herself a 30th birthday party to celebrate another decade and a clean slate with a new man by her side.

Chleb is on the receiving end of Kathryn’s anger and makes a big decision. Austen is hurt that Craig didn’t tell him about hooking up with Naomie and suspects the former couple is hiding an even bigger secret. Naomie decides to throw a party where Austen tries to confirm his suspicions. Olivia defends Kathryn, causing a rift between her and Venita.

Austen gets emotional when he learns his parents are selling his childhood home; Chleb leans on his cousin for support in the wake of his break-up with Kathryn; Shep's past comes back to haunt him when Taylor voices her concerns for their future.

The boys have a barbecue and while the grill gets hot, the drama does too; Craig looks to Paige for advice on how to mend his friendship with Austen, but Austen's got bigger fish to fry when he learns some shocking news about Madison.

Austen finds it hard to bite his tongue when Shep feels attacked by the group. After a day of golf and shrimping, an English countryside dinner sets standards high for a civilized evening, but some guests have other plans. Naomie leans on her friends for support when Craig lashes out, but finds Venita’s allegiance is elsewhere.

Craig faces the wrath of those he wronged at his holiday party. Venita faces the reality of her failing friendships. Leva gives us a peek into her new show. A scorned Taylor reveals the truth about the end of her relationship with Shep.