Patricia surprises Cameran by planning a glamorous retro baby shower, but not everyone gets an invite. At the shower, Craig and Naomie fall back into old habits and an unexpected guest turns the event on its head. As Cameran begins to face the realities of becoming a new mother, Kathryn makes up for lost time with her kids. Meanwhile, Thomas considers his future with Ashley.
Kathryn takes the high road by inviting Thomas’ new girlfriend, Ashley, to lunch. Meanwhile, as Cameran’s due date approaches, her anxieties over becoming a mom subside. After spending time with Cameran, Chelsea begins to fear motherhood may never be in her future. Austen concocts a plan to get Craig back in the dating saddle. Unfortunately, Craig’s sights are set on winning Naomie back until a heated conversation between the pair threatens their future.
As Thomas ponders his next steps with Ashley, Patricia encourages him to propose. Austen's parents push him to make some strides professionally, while Craig hires a coach to help him get his life on track. Naomie gets wind of Craig's new crush, and turns Austen's Halloween party into a house of horrors when she comes face to face with the woman.
Naomie prepares to open her family's new restaurant, and finally comes to terms with the fact that she isn't over Craig. Meanwhile, Patricia and Craig have a heart-to-heart about relationships. Cameran tries an old fashioned trick to get baby Palmer to make an appearance with the gang. Thomas gets himself into hot water with Ashley after she sees him flirting with Kathryn. Meanwhile, Shep steps in to help Austen and Chelsea define their relationship.
Cameran suspects that she may be experiencing labor pains. Kathryn prepares for her first day of work, while Craig helps Austen realize things are over with Chelsea and refocuses on wooing Victoria. Patricia tries to make Ashley into the perfect Southern Belle and hosts a dinner party with the men of Charleston to test her skills. At the party, it seems Thomas only has eyes for Kathryn...and he may not be the only one.
Cameran plays the pregnancy waiting game while the rest of the gang prepares for a trip to Shep and Chelsea's hometown, Hilton Head. Meanwhile, feuding exes, Craig and Naomie, attempt to act civil with the help of an old furry friend. Austen decides to rekindle his romance with Victoria, but fears Chelsea's reaction. As Kathryn plans her son's birthday, Thomas' girlfriend gets sour from the invitation snub. Tensions flare at a beachfront argument, changing one relationship for good.
Emotions run high during the gang's first night in Hilton Head, when Ashley confronts Kathryn. After the group is forced to pick sides, everyone is walking on eggshells for the rest of the weekend. When the last flare up comes, it's Austen who gets burned when a flirtation with Chelsea comes back to haunt him.
As the Hilton Head trip comes to an end, Shep visits his mom and finally admits some truths about himself, as Chelsea takes a trip down memory lane and opens up about her past. Meanwhile, back in Charleston, Austen attempts to make amends with Victoria, and Cameran finally welcomes her new bundle of joy. When everyone comes together to celebrate Saint's second birthday, Thomas and Kathryn finally find the sweet spot with their co-parenting. Ashley, on the other hand, has a bone to pick that might just send her packing.
Austen prepares to debut his beer to his family and friends and Craig makes progress on his pillows for Patricia. Cameran tries to adjust to her new life with baby Palmer, while Kathryn and Shep spend some quality time together. Ashley returns from California, but her relationship with Thomas is still on the rocks. Meanwhile, Chelsea and Victoria finally cross paths at Austen's beer tasting event, putting him on the spot about their relationships.
After basking in the glory of his successful beer event, Austen is hit with romantic reality and Craig faces some harsh truths. Meanwhile, as Thomas and Ashley struggle to resolve their issues, Chelsea feels vindicated when she hears some news from Shep. Cameran finally gets to enjoy some freedom from motherhood, Kathryn goes MIA and her friends fear the worst.
Thomas continues to pressure Ashley to get a job in Charleston, leaving them in relationship limbo. Meanwhile, Chelsea and Austen come to terms with the state of their friendship, while Craig and Naomie, once again, try to navigate dating post break-up. After Thomas invites the gang to watch him play in his last polo match out at Brookland Plantation, Kathryn must face her fears of returning to the place she thought would be her happily ever after.
After 5 years of constant tension, Patricia finally extends an olive branch and invites Kathryn to her Winter Ball. As these two former enemies make peace, the delicate truce between Craig and Naomie blows up when he brings a date to the Ball. Meanwhile, as Austen tries to warn Thomas that there's a nasty rumor circulating about Ashley, he's the one that gets burned by Ashley. When Kathryn and Ashley finally sit down to talk for the first time since Hilton Head, their conversation quickly turns combative.