Surprising Love Revelations: Unveiling the Romances of Chesapeake Shores Cast

Attention all Chessies! Hallmark Channel enthusiasts have shared laughter, tears, and heartfelt moments alongside the beloved cast of Chesapeake Shores since 2016. Behind the scenes, fans have also become captivated by the genuine friendships and romantic lives of the stars.

When Chesapeake Shores first graced our screens, we were introduced to the endearing O'Brien clan. Eldest sister Abby O'Brien (portrayed by Meghan Ory) makes her way back to her hometown following her divorce, accompanied by her two children. This reunion brings Abby back into the loving embrace of her sisters Bree (played by Emilie Ullerup) and Jess (portrayed by Laci J Mailey), as well as her brothers Kevin (portrayed by Brendan Penny) and Connor (played by Andrew Francis).

The O'Brien family is not complete without Megan (Barbara Niven) and Mick (Treat Williams), who set a great example for true love. Fans have been captivated by the romantic ups and downs of all the O'Brien children, especially Abby's love life.

In May 2021, Jesse Metcalfe, who played Trace Riley, Abby's former high school sweetheart, surprised viewers when he announced his departure after five seasons. Metcalfe revealed in an exclusive interview with We in October 2020, prior to his final appearance, that he had personalized the role to fit himself. "I tailored that role specifically for me. I mean, the series is based on a book series where the character is an architect. So I had the freedom to completely transform the character and make him more like me."

Evan Kincaid, portrayed by Robert Buckley, became Abby's new love interest, leaving fans curious about her eventual happy ending. In August 2022, Chessies finally received the answer as the long-awaited sixth and final season premiered.

Even though the 10-episode finale marked the end of the series, fans can take solace in knowing that the close-knit O'Brien clan will still be seen. The cast, who are great friends off-screen, have openly expressed their fondness for each other following the conclusion of filming.

"After 6 seasons, I am happy to announce that filming for #chesapeakeshores has come to an end! It has been quite a journey, starting with #hyperemesisgravidarum and ending with #covid," Ory shared on Instagram in July 2022. "I want to express my deep gratitude to our incredible cast and crew for their patience with me during my struggle to not get sick around anyone."

Ory also took a moment to acknowledge her "amazing" husband John Reardon for being her rock and holding everything together. She added, "I also want to thank our two wonderful nannies, without whom we couldn't have managed. With both parents working on TV shows, having two nannies was a necessity! #ittakesavillage. I sincerely hope that everyone who watches enjoys the final season! Xo."

Ory's TV sister, Ullerup, also became nostalgic when bidding farewell to her colleagues in the same month. "I had the privilege of portraying the daughter, sister, and brother of these incredible and eccentric individuals for six years. This has been the longest-standing job in my career," she expressed alongside a group photograph. "Countless events unraveled in our imaginary world, as well as in our personal lives. It was a comforting feeling to have a second family to share both the highs and lows with."

The Love & Glamping star, whose real-life husband, Kyle Cassie, made several appearances on the show as Martin Demming, concluded, "I am confident that each and every one of them will move on to accomplish great things, as they are genuinely gifted individuals. I will forever cherish the blessings that #chesapeakeshores has bestowed upon me. What an incredible journey, family."

Scroll down for a complete guide to the cast’s real-life romances:

Credit: Ricardo Hubbs/Crown Media United States

‘Chesapeake Shores’ Cast’s Dating History: Inside the Hallmark Channel Stars’ Love Lives

Attention all Chessies! Since 2016, Hallmark Channel fans have had the pleasure of laughing, crying, and falling in love with the captivating world of Chesapeake Shores. But beyond the screen, fans have also become engrossed in the fascinating friendships and romantic journeys of the show's stars.

When Chesapeake Shores first premiered, viewers were introduced to the endearing O'Brien family. Eldest sister Abby O'Brien, portrayed by Meghan Ory, returned home after her divorce, accompanied by her two children. This reunion brought Abby back into the loving embrace of her sisters Bree, played by Emilie Ullerup, and Jess, portrayed by Laci J Mailey, as well as her brothers Kevin, played by Brendan Penny, and Connor, portrayed by Andrew Francis.

The O'Brien family relies on both Megan (Barbara Niven) and Mick (Treat Williams) to set an example of what true love looks like. Fans have been captivated by the romantic highs and lows of all the O'Brien children, with Abby's love life being a major focus. However, in May 2021, viewers were surprised when Jesse Metcalfe, who portrayed Abby's high school sweetheart Trace Riley, announced his departure after five seasons. Prior to his final appearance, Metcalfe shared in an exclusive interview with We in October 2020 that he had tailored the role to his own personality, deviating from the character in the book series where Trace is portrayed as an architect.

In August 2022, fans of the beloved series finally discovered if Abby would find her happily ever after with new love interest Evan Kincaid (portrayed by Robert Buckley) who quickly entered her life and filled the void. The sixth and final season, consisting of 10 episodes, provided the long-awaited answer.

However, the finale did not mark the end of the O'Brien clan for fans, as the cast members are close friends in real life. In fact, many of the stars have already expressed their affection for each other after completing filming for the series.

The final season of #chesapeakeshores has come to a close after 6 seasons. Despite dealing with #hyperemesisgravidarum at the beginning and #covid towards the end, it has been an incredible journey. Ory expressed her gratitude to the cast and crew for their patience as she battled through her illness. She also gave a special thanks to her husband, John Reardon, for his unwavering support. With both parents involved in TV shows, they relied on not one, but two Nannies to help with their busy schedules. Ory hopes that everyone who watches the final season will enjoy it. Xo.

Ory's TV sister, Ullerup, also became emotional when she bid farewell to her work family during the same month. Reflecting on her experience, she expressed gratitude for portraying the roles of daughter, sister, and brother to these wonderful and eccentric characters for six years. This has been the longest-running job of her career, providing both professional and personal growth. Ullerup cherished the moments shared in their fictional world and appreciated having a second family to navigate through life's highs and lows. Additionally, Ullerup acknowledged the exceptional talent of her colleagues, expressing confidence that they will embark on successful endeavors in the future. She concluded by expressing everlasting gratitude for the gifts and opportunities that #chesapeakeshores bestowed upon her. It was truly an incredible journey with her "fam."

Scroll down for a complete guide to the cast’s real-life romances:

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Meghan Ory

The leading lady of the show tied the knot with Reardon, a Canadian actor, in 2008. Since then, they have been blessed with three children, the youngest of whom was conceived during the filming of season 6 of the Hallmark series.

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Brendan Penny

Penny has been married since August 2010. He shares two children with his wife and has chosen to keep all of their names private.

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Laci J Mailey

Mailey wed Steve Bradley in July 2016. The twosome welcomed son Cassius in October 2019. They expanded their family in March 2022 with the arrival of their daughter.

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Andrew Francis

The Canada native celebrated his five-year dating anniversary with Carrieann Bailey in March 2022. The couple share two dogs, Mystic and Spirit.

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Emilie Ullerup

The Danish actress and her longtime partner Cassie got married in 2015, but they postponed celebrating their wedding with friends and loved ones until August 2018. In January 2020, the couple joyfully welcomed their first child, a son named Wilde.

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Treat Williams

Williams married Pam Van Sant in 1988, and together they had a son named Gill in 1992 and a daughter named Elinor in 1998. Tragically, Williams passed away at the age of 71 in June 2023 due to a motorcycle accident.

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Barbara Niven

The Oregon native was married to British film producer David Niven Jr. from 1993 to 1998. The exes share one daughter, Jessica.

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Robert Buckley

Buckley, who debuted on the show as Evan Kincaid in 2021, embarked on a whirlwind romance with Lea Michele back in 2016. After parting ways in July of that same year, the One Tree Hill star found solace in the arms of Jenny Wade. The couple exchanged vows in May 2018, and three years down the line, their love story blossomed with the arrival of their adorable baby boy.

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Diane Ladd

The Mississippi native, who portrays grandma Nell O'Brien, has had three marriages. Ladd and Bruce Dern were married for nine years until their separation in 1969. The former couple has two children, actress Laura Dern and the late Diane Dern, who passed away in 1962 as a young toddler. Following her divorce from Dern, the Alice alum tied the knot with William A. Shea Jr. in 1969, but they ended their marriage in 1976. Currently, Ladd has been happily married to Robert Charles Hunter since 1999.

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Jesse Metcalfe

In January 2020, we exclusively revealed that the renowned actor from "John Tucker Must Die" and his fiancée, Cara Santana, decided to end their 13-year relationship. Later that same year, Metcalfe began dating model Corin Jamie-Lee Clark and openly acknowledged their love in December 2020. Fans may recognize him from his role as Trace Riley on the beloved Hallmark series, which he portrayed from 2016 to 2021.

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Jessica Sipos

Sipos, who plays Sarah Mercer, Kevin's wife, tied the knot with Nicholas Lendvoy in July 2013. In April 2020 and March 2022, they joyfully welcomed their son, Woods, and daughter, Dru, respectively.

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Carlo Marks

The actor, who plays Jess’ husband, David Peck, is in a long-term relationship with Shivani Ruparelia, who first popped up on his social media pages in early 2017.

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Gregory Harrison

Since 1980, the Falcon Crest alum has been in a marital union with Randi Oakes, who is both a model and actress. Together, they have four children: three daughters named Emma, Kate, and Lily, as well as a son named Quinn. Starting from 2017, Harrison has been portraying Mick's brother Thomas O'Brien.

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Greyston Holt

In July 2022, Holt made an exciting announcement about the upcoming arrival of his first child. After being in a loving relationship for over a decade with Cristina Rosato, the Canadian actor shared the joyous news. Their journey together began in 2011, marked by their early days of posting photos on social media. Holt became a part of Chesapeake Shores in 2019, showcasing his talent as Jay Ross.

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Stephen Huszar

In 2021, the Canadian actor, Huszar, played the role of Luke Tatum in nine episodes. While he has charmed numerous leading ladies in his Hallmark Channel films, it wasn't until June 2023 that he publicly confirmed his real-life relationship with Katie Cassidy, his co-star in A Royal Christmas Crush.