Danni Baird and Taylor Ann Green did their best to tame Shep Rose, but these relationships both failed. This season, Shep fell head over heels in love with Sienna Evans, making fans think he was finally ready to settle down. But, nope. This connection also crashed and burned, chiefly because Sienna had no clue she and Shep were dating.
Shep plays the ultimate Peter Pan character on Southern Charm. This narrative is perfectly okay, as not everyone wants a white picket fence and the same plus one for life. However, in recent years, Shep has made mention of settling down and starting a family, so he was pretty bummed that Sienna and he failed to last.
Charmer Shep has kissed many saints in seasons past. He even had a spinoff series, RelationShep, which aimed to help Shep find his one. But sadly, his match from this series also sank. As Season 10 of Southern Charm wrapped, viewers thought Shep might have found his soulmate, but, nope, again.
Shep has dated many potential Mrs. Roses. We will recall these ladies below.
Before Southern Charm existed, Shep Rose dated Danni Baird
Danni and Shep dated long before the cameras picked up to film Season 1 of Southern Charm. They only dated for a handful of months. Luckily, nothing terrible seems to have transpired, as, after their split, they remained close friends. But in Season 6, a secret was spilled that hurt Shep and Danni, courtesy of the muppet-mouth moniker maker, Madison LeCroy.
In 2019, the cast took a trip to Colorado. Chaos touched every cast member in attendance, as usual for this series. As for this long-broken-up couple, Madison claimed that Shep gifted Danni with chlamydia back when they were dating. Looking equally appalled, Shep and Danni denied her hurtful allegation.
Danni exited filming only one season later. She has since found her prince and is living her best life as his bride. They welcomed their first child, a son, in 2023.
Starting in Season 1 of Southern Charm, Shep Rose and Kathryn Dennis held a friends-with-benefits-styled relationship
Shep and Kathryn Dennis never dated. However, there were many seasons where it felt like one or the other would have loved to take this leap. As a forever fan of Southern Charm, I always loved how Shep stuck up for Kathryn. He was always happy to see her face, which she needed, as many of her costars felt differently.
In 2018, Kathryn admitted that she and Shep hooked up multiple times. These hookups happened before and after she welcomed her two children with her ex-who-shall-not-be-named. On Bravo, Shep pondered if they cut the cord too soon, noting that he had fun with Kathryn, as they could be themselves around each other. On Watch What Happens Live, Shep added that he and Kathryn had at least six or seven sleepovers, yet nothing serious came of this fling.
Shep Rose and Landon Clements shared a flirtatious bond during Season 3 of Southern Charm
Landon Clements held no love for the duo of Shep and Kathryn. Landon and Kathryn never saw things eye to eye, as Landon found Kathryn manipulating and tiring. But Landon loved Shep, which she put into the universe during Season 3 of Southern Charm.
Shep and Landon flirted often, but in Episode 10, this all came to a crashing halt. When Shep gave Landon an update on his life, announcing that he was newly single, Landon slid in with a sultry-like statement. First, Landon admitted that she was jealous of his other relationships. Then, using a voice I still hear, Landon said, “Maybe I love you.”
Landon further explained that she had loved Shep for a while. In response, Shep choked on his red wine.
During Season 4 of Southern Charm, Shep Rose pined after Chelsea Meissner
Chelsea Meissner is one of my favorite Southern Charm alums. During Seasons 4 – 6, Shep felt the same way as me. He flirted with Chelsea throughout her earlier seasons, only to get rejected multiple times. However, Chelsea did have feelings for someone in their cast, just not for Shep. Instead, Chelsea dated Austen Kroll, a longtime buddy of Shep.
On the After Show for Season 5, Episode 16, Chelsea explained that she and Shep could never be. He parties too much and fails to work, so Chelsea is not receptive to his advances, Chelsea quipped. Chelsea is now living that single life away from the lenses of Bravo. She and her little daughter are happy and healthy.
In 2017, Shep Rose starred in RelationShep, where he fell for Bella Clark
Shep failed to find love in Charleston. Therefore, a spinoff series called RelationShep arrived in 2017. After a few weeks of searching, Shep introduced a shocking plot twist during the finale when he ended things with his final two bachelorettes. Then, Shep announced that Bella Clark, a 24-year-old brunette who had left filming in favor of her job back in New York City, had stolen his heart.
Shep and Bella tried dating after this series wrapped. However, their ages and locations created challenging narratives, as both held different priorities on what they wanted out of their lives. Now, Bella is married to another suitor. Likewise, several years later, Shep experienced his longest relationship to date (see below).
Shep Rose and Taylor Ann Green dated during Seasons 7 and 8 of Southern Charm
Shep began dating Taylor in 2020, AKA Season 7 of Southern Charm. During the reunion, airing in January 2021, Shep confessed to cheating on Taylor. Even still, Shep and Taylor moved past his infidelity, only to then break up in 2022. During the reunion for Season 8, Taylor emotionally opened up about their split.
Taylor accused Shep of sleeping with over 300 women during their two-and-a-half-year relationship. He apologized for any pain he caused her. However, Shep denied being a chronic cheater. Like many others on this list, Taylor has moved on to another admirer.
Taylor and Shep are mostly cordial on Southern Charm, where Taylor now holds a front-row seat to her ex’s hard-fought, still not won, relationship pursuits.
Season 10 of Southern Charm showed Shep Rose in a one-sided relationship with Sienna Evans
During Season 10 of Southern Charm, Shep found his one true love, or so he thought. Shep met Sienna on Raya, a members-only dating site. He was immediately in awe of her beauty pageant looks and freckly lips. Nearly twenty years her senior, Shep and Sienna began hanging out, and, as Shep revealed on air, he fell in love with this woman almost straight out of the gate.
Cue a cast trip to the Bahamas, her homeplace. To everyone but Shep, the writing was on the wall. Sienna did not care for Shep as he cared for her. Sienna did not even know they were officially dating, prompting Shep to override her statements, indicating they were both in love.
(CLEARLY), Shep and Sienna are over.
Shep Rose hooked up with Molly O’Connell at the end of Southern Charm Season 10
Molly O’Connell is a delightful addition to the cast of Southern Charm. When Molly and her tuba appeared in Season 10, a sense of lightness filled her scenes. Likewise, Molly saw an equally bright ray in Shep, her crush. Unfortunately, her affections were tough, as Shep was “dating” Sienna during this same timeline.
But then, the stars aligned at the end of Season 10. Shep escorted Molly to their summer kick-off bash, where Molly went in for the kill, kissing Shep with all she had. Her dry spell then ended, the producers cheekily noted at the end of the Season 10 finale. During the reunion, they confirmed that they slept together twice, but both are still single.
The soulmate search now continues for Shep.
Southern Charm is streaming on Peacock.
TELL US – DO YOU THINK SHEP WILL ONE DAY PUT A RING ON SOMEONE? IF SO, WHO DO YOU SEE SHEP WITH, ROMANTICALLY SPEAKING? (WRONG ANSWERS CAN ALSO APPLY – FOR FUN).
This story originally appeared on Realitytea
